One, quite introspective, I write personal essays reflecting on the lessons and discoveries I had so far on the journey of creating a meaningful life. The other, on the contrary, is very much outward focused, I write to help you create a personal brand, a body of work on the internet, express yourself, and find your unique angle.

But today, I found the point where both converge.

I realized that they were never conflicting, they were just different angles of one clear exploration: How self-expression influences the shaping of a meaningful life.

And to deepen this exploration, I invited Dr. Hermano Castro, psychiatrist and psychotherapist, and content creator focusing on areas of human behavior and relationships, to help us answer questions, and make connections that were still vague for me.

I have followed Dr. Castro’s work for many years, which has helped me so much along my journey. He also published the book Communicating Like an Adult — one I almost begged him to translate into English. I’ve never found a book quite as helpful and practical on self-expression and communication.

We talked for a little over one hour, touching on topics like identity, purpose, personal opinions, relationships, and so on. Trimming his insights for a written piece was one of the hardest jobs I ever had. I did my best and my recommendation is: grab a good cup of tea, and set aside 20-30 minutes to read the full interview. It’s worth every line of it. He left me 🤯 the entire time.

But, just in case you want to explore around, or go straight to your area of interest, I broke down the interview into four parts:

• Part 1 - What it means to live a meaningful life and what’s the role of self-expression in it?

• Part 2 - Communication and relationships

• Part 3 - Communication and work

• Part 4 - Communication and the internet

After reading this, you won't see yourself the same way. Now, enjoy! And let me know what part resonates the most with you!!

Part 1 — What it means to live a meaningful life and what’s the role of self-expression in it?

(1) Nathalia: The theme of the interview is how self-expression influences the creation of a meaningful life. My first question for you is: what would be your definition—your view—of what a meaningful life is?

Hermano Castro: This is an excellent question, because I always say that the definition of words matters. Sometimes we use words without reflecting on what they mean.

When someone says “I want to live a life with purpose, a meaningful life”, we have to start from this person’s understanding of what that means. Otherwise, how will you know whether you’re living it or not? We need to define the starting point.

And I like to point out that a meaningful life is much more a feeling than a concept. If I ask someone, “Do you live a meaningful life?”, they can feel whether they do or don’t.

“Yes, I feel my life is meaningful.” They don’t necessarily know how to explain what makes it meaningful, but they can feel it. So the first point is that meaning—this idea of meaning—is a feeling to be accessed, with many individual and subjective nuances.

If I put it more practically, I like to think that a meaningful life is one in which I understand there are goals to pursue—goals with value and meaning—and I understand that I’m able to walk that path. I can advance on that path at my own pace, as I enjoy moving through it.

So, in other words: I’m living a meaningful life when I’m moving toward goals I consider valuable, while I enjoy the path, and gradually feel I’m moving closer to what I desire.

If I don’t know what goals I’m moving toward, or if I set them but I don’t even know if they have value or meaning to me, it will result in you setting goals while feeling stuck.

You won’t be able to progress and you won’t know why. You will probably fall into that abyss of feeling that life has no meaning, or it does have meaning but you can’t reach it.

(2) Nathalia: When you talk about setting goals, connected to the idea of purpose, I’m curious where these goals come from? What should one look for to become aware of them? Is it something we find or is it something we develop?

Hermano Castro: We can think that our life is made up of different dimensions. When we think about goals to pursue, we can think of it through these dimensions: interpersonal life, intrapersonal life, professional life, family life, hobbies, material goods, spiritual life, community life, etc.

So, when someone says “I want to improve my social life”, we have to be clear on what this means: you want to improve it in what way? Where are you now and where do you want to get to?

The same thing when people say “I want to improve my love life.” Ok, but how?

“I want to improve my family life, my material life, my intrapersonal life, my spiritual life, my community life, my professional life.” From each dimension, we already have a broad range of possibilities. But it’s not necessarily clear what I want to achieve in each dimension or why I’d like to achieve that.

And that brings us to a more philosophical concept I find fascinating from analytical psychology—Carl Jung, for example—who brings a wonderful concept worth sitting with called circumambulation.

Here’s what’s interesting, Nathalia: if you notice, we don’t choose our interests; in a certain way, they choose us.

For example: when you say “I love country music.” You didn’t decide to like it by your own free will. One day a rock song played and you didn’t like it, a jazz song played and you didn’t like it either. Then a country song played and you liked it. Why? Who knows.

We can try to explain, but it remains mysterious.

Our interests reveal themselves to us. What we find meaningful in life is more perceived than decided.

So, you might say, “I want to improve my professional life; I want to be a lawyer.” What exactly makes you want that? What do you feel when you imagine yourself as a lawyer? How does it move you or not move you?

The answer to the question “How can I find my purpose, or goals that feel meaningful?” is to identify what moves you, what calls you, what elicits your impulse and enthusiasm.

Enthusiasm is a word I love. If you look at its etymology, it means “God within”, a feeling of fervor toward something you don’t choose to feel; you’re taken by it.

At the same time, this requires connection with yourself, because you have to perceive what happens inside you when you face these possibilities. And often we are disconnected, looking to see whether others will like it, whether we’ll be approved, whether someone will get mad, rather than noticing what’s happening inside of us.

In summary: we can think about different dimensions of life and identify the “track” of enthusiasm in each one—where I am now and where I’m being called to.

From that calling, I can refine and shape my next step. I don’t have to be impulsive: “My enthusiasm tells me to drop everything and backpack.” You could do that, and sometimes it’s exactly what you need. But you can also use discernment, thinking about a life project that makes sense given your reality, context, and enthusiasm.

Those are good guides to find purpose. What do you think?

(3) Nathalia: Fascinating. I’ve never thought of it that way. Now that we covered the definition of what a meaningful life is, I’m curious if for you communication and self-expression are synonyms or different things?

Hermano Castro: They can be synonyms in some contexts. Communication means bringing information into the world, to materialize what is inside you and to externalize it in a comprehensible way.

This intersects with expression. To express means placing yourself on the stage of life. Life is happening; and you decide whether you want to participate in it or not.

To express is, in a sense, to communicate your identity—who you are. In that sense, yes, they can be synonyms.

(4) Nathalia: Why does having an opinion/a point of view contribute to a more meaningful life? Does that conclusion make sense?

Hermano Castro: Yes, at some level. Even if that opinion is built on faulty ground, self-expression doesn’t necessarily mean saying or doing things the “correct way”; it means participating.

We can also participate in life by making mistakes, and there’s nothing wrong with that.

Having an opinion is communicating to the world what you constructed from what you lived. You had experiences, gathered information, and synthesized: “This is how I understand what’s happening.”

That synthesis you concluded can have many faults in it, and that’s fine if you’re open to being challenged. Ideally someone, in good faith, can point out your gaps of perception and understanding, and from there you can form a better opinion.

The alternative is: If I never express an opinion, I’m not formulating a worldview, maybe because I’m distracted or afraid to express. The consequence is that other people won’t know how I see the world, which makes it harder to interact with me. It can even make it harder to feel connected or compatible.

At the same time, we can fall into the trap of thinking we must have an opinion about everything. You don’t necessarily need to. You can say: “In my view, I don’t have enough information to go deeper.” That is also an opinion, it tells others something about your identity and what you’re interested in or not.

Different people will react differently to your opinion of not wanting to add to a topic, some will try to teach you, some won’t engage with you, others will listen and identify with you. What you express in the world will shape how other people will interact with you and at what level of interaction that engagement will take place.

(5) Nathalia: You talk about expressing opinions as if expressing one’s identity. What is identity in this context?

Hermano Castro: Opinions are more volatile than identity. You can change your opinion instantly with new facts.

But sometimes for some people, changing an opinion would also mean changing a relevant part of one’s identity, which is why people try to resist it. People who experience this make the mistake of thinking that an opinion represents the totality of their identity.

Generally speaking, our identity is one of the mental aspects that we dedicate the most effort to defend and protect.

One definition I find fascinating is: identity is the set of emotionally relevant experiences through which you narrate your individual story.

If I ask “Nathalia, who are you?”, you’ll narrate facts: I’m from Brazil, I work with communication, I’m the daughter of... etc. You won’t tell me “I’m someone who ate eggs for breakfast or watched cat memes in bed”, because for you, those aren’t emotionally relevant.

We experience the world through the frame of a narrative. What composes this narrative are the emotionally relevant experiences we have. That set forms your identity.

Taking this concept a little further: identity is the role you believe you play on life’s stage. How did you decide to take on that role? Through the emotionally relevant experiences you gathered throughout your life.

That’s why it’s important to tie purpose to enthusiasm: enthusiasm is a strong emotion.

If you do things only because others told you, it may not be incorporated as deeply as when it’s connected to your desire. The more you have emotionally relevant experiences in different dimensions, the more solid your sense of identity becomes.

There’s a trap that can result in a weak sense of identity, which is when we build our sense of identity from intense emotions like arguing, fighting, or proving ourselves right. If that’s all someone has as their identity, it will be very hard to change this, because this person will end up concluding that if they lose that, they are left with nothing else that makes them feel relevant.

So they defend opinions fiercely because they confuse “any opinion” with “my whole identity”.

(6) Nathalia: If I feel I’m not living a meaningful life, could it be because my identity/narrative doesn’t open doors for that? Is it possible to change one’s identity to connect to a deeper sense of meaning?

Hermano Castro: Yes. We do it all the time, not necessarily consciously.

Many people grow up as projects of their parents or society. They don’t identify with it and don’t feel emotionally relevant experiences through it.

Then they realize other experiences would make them feel more connected, and they move toward them.

Like someone who was supposed to be the family doctor but, in the middle of medical school, they realize that music is what feels meaningful for them, and they leave medical school and go in pursuit of music.

So their identity shifts from “family’s doctor project” to “musician living a creative life.”

We are constantly reconfiguring our identity throughout life as a whole, through each moment we live, based on the experiences that are presented to us by life.

(7) Nathalia: And what if someone feels like they lack purpose and don’t know what path to explore moving forward? How can someone decide what experiences to explore when these experiences are not being spontaneously presented in their lives?

Hermano Castro: Perfect. This is common in the clinical practice. A patient arrives at their 20s, 30s, or 40s saying: “I’m lost… I don’t know what to do... I have no purpose.”

The first inevitable step is to get to know yourself, because before deciding where you want to go, we will identify where you are now and why you’re in this place.

If you don’t know where to go, why is that? What happened in your life that prevented your path from being revealed?

Sometimes you lived a life where no one was interested in your interests; no one noticed your signals when you were drumming on the table and thought “well, maybe he’s into percussion.” There was never a person who noticed that you hated leaving the house, but whenever it was to go out to nature, you loved it.

On the other hand, we could have lived a life where we were restrained. Whenever you were drumming on the table, someone told you to stop it. Or whenever you were excited about nature, they told you it was nonsense, and pushed you in another direction.

That’s how you disconnect from your interests and focus on what others want. You lose the ability to validate your own interests.

So first we understand: what kind of life did you live? What interests showed up? What was suppressed? What paths were you directed toward? What were your doubts and existential dramas? All of that points to your interests.

In essence, you need to identify those interests because they will need pursuing, at least on some level.

So we revisit the person’s life story and map it. Instead of skipping ahead to “find purpose,” we first understand the deep reasons you haven’t found it yet.

One step at a time.

Nathalia: I love how clearly you laid out stages so people can locate themselves on the path.

Hermano Castro: Yes. We sometimes think of self-knowledge as something navel-gazing, but it has practical utility: to orient you. When you know yourself, you know which directions interest you more or less, where you have aptitude or limits. Self-knowledge sharpens your decision-making.

(8) Nathalia: Usually when people say they want to communicate better, they are advised to seek a public speaking course, or a writing course, or any way that helps them with articulation. What would be your advice for someone who wants to develop their communication and self-expression skills both in personal relationships and at work, or any other sphere?

Hermano Castro: That’s a great question. Communication is a tool, a tool for connection. That’s the purpose of communication.

The better I communicate, the better I express what’s inside me so others can understand clearly who I am and what I want. So, before starting a speaking course, start with your goal: what do you want to communicate, aiming at what goal? What are you envisioning?

In my book ‘Communicate like an adult’ I define the first pillar of communication as defining your goal or intention.

If I want to communicate better with you, I need to know: ****what I want you to know? With what intention? How would I like you to act based on that? If I don’t know the answer to this, I can have the most sophisticated vocabulary or articulation, but I won’t necessarily connect with you.

To connect with you, it helps to be connected with myself. I know who I am, what I want, what I prefer, what could help me or harm me. Then when I approach you for a conversation I take all that I know about myself and try to put it into comprehensible words.

If I don’t know who I am and what I want, it’s common to find myself in the situations we hear about in romantic relationships when we hear “You have to improve your communication”.

Let’s say I don’t like that my girlfriend acts in a certain way. So I need to improve my communication with her.

But if I don’t know what a different way I’d prefer her to act looks like, in what way does her current behavior bother me? If I don’t know, then we have to step back, and first understand myself.

Sometimes someone connected to themselves can help you communicate—ideally that would happen in family systems, but often it doesn’t.

Still, we can catch up and develop this skill ourselves.

Part 2 — Communication & Relationships

(9) Nathalia: We all hear that to improve our relationships and conflicts, we need to improve our communication. I think that there are people, like me, who believe they communicate well, but I also believe that we all have blind spots about our own capabilities and skills. What question would you ask me that would reveal my real ability to communicate well right now?

Hermano Castro: Communication is a tool for connection. If you want to know how well you communicate, evaluate how connected you feel to other people.

If you say “I communicate very well.” I ask you: “Do you feel you have good relationships?”. If not, there are two possibilities:

1. You’re in a place surrounded by people who truly don’t know how to connect, and you may be a victim for being surrounded by them; or

2. You may not know how to connect with others.

Connection takes two people. You might be able to communicate really well, but if the other person is at an initial level, there’s a limit to what’s in your control.

After I launched my book How to communicate like an adult, I started receiving messages from people like: “I did everything you recommended in your book but my partner is still difficult.” Communication isn’t a tool of control, that would be manipulation.

Even if you communicate clearly, the other person may have a “dirty lens.” Your message may be clear, but their perception may not be clear. So you can recognize: “Within what’s my responsibility, I communicated well, even if they may not be able to see clearly.” You can invite them to wipe their lens clean, but you can’t force them to see your side or communicate at the same level.

So, being aware of this, we can avoid falling into some traps of taking on responsibilities and guilt that aren’t ours. Because maybe the other person isn’t so open or willing to connect with you at the same level you are.

When we look at the collective, we can have a better idea of our own capacity for communicating well: if you can’t connect with anyone, maybe it’s not only a matter of skill; it may be your connection with yourself.

It’s easier to connect with others when you’re connected with yourself.

(10) Nathalia: There’s a biblical saying “If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you”. In your perspective, what is the impact of not expressing ourselves fully in a romantic partnership, or in our friendships, both for the one who doesn’t express and for the relationship in itself?

Hermano: We could do an entire interview on that. Using the biblical metaphor: there are sins of commission and sins of omission. We often underestimate omission.

You can be wise in what you express, you don’t need to express everything impulsively, because that would be indistinguishable from a 2-year-old child.

You can be wise in your communication when you understand what would work best to connect with the other person, while having clarity on what goal you’re aiming for with what you want to communicate.

Omitting can be dangerous because people think it maintains peace. Sometimes it does, if it’s something trivial you can truly let go. But sometimes it’s relevant, and if you don’t communicate it, it keeps circling in your head and tormenting you.

Sometimes, it’s important information about who you are or how you feel, and you’re depriving the other person of knowing that. And when you do so, you are also depriving yourself of discovering who they are in response to what you have to share with them.

We get to know each other not only by what we reveal to others about us, but also by observing what their reaction is to what’s revealed to them.

For example, let’s say you made a mistake and you don’t want to communicate it because the other person might react badly. Assuming so, it’s not like they wouldn’t be that person anymore just because you omitted this information from them. They will continue to be a person that reacts badly whenever they learn about a mistake you made.

If you know how they will react in the face of this, you will also discover if they are open to doing something to change this inadequate behavior. And with this information, you can decide what level of bond you want to cultivate with this person.

Another point is that omission breeds resentment, and the more resentment is built, the more disconnection happens between people.

Sometimes when we express ourselves we can generate some conflict indeed, and the problem is that people think that conflict is something horrible to happen. Conflict is uncomfortable in the short term, but avoiding it can become a bigger debt later. Would you rather experience X discomfort now vs. 10x discomfort in the future?

There’s no right or wrong, but knowing now that this is how things work, you can decide for yourself.

(11) Nathalia: So communication is both a tool to express and understand who we are, and to understand who the other person is based on how they receive that information.

Hermano: Exactly. And I like to reinforce this to my patients so we don’t fall into the trap of thinking “if I communicate really well, everything in my life will be perfect”, “If I communicate really well, the other person will always be nice and respectful to me”. This is not necessarily true, and not necessarily bad.

Sometimes the other person can respond angrily to me because the way I communicate is actually bad, and I didn’t realize I was disrespectful because I’m used to speaking in this certain way.

But if I know that I worked on my communication skills, and I know how to reach out to you respectfully, and still you respond to me in an aggressive way, this is valuable information about who you are that is being revealed to me: that you are aggressive with me even though I addressed you respectfully.

I can consider whether this happened because you’re feeling overwhelmed in this specific moment? Maybe that’s something happening in your life that stressed you out? Or is this a pattern that keeps showing up no matter the circumstances?

So, I can propose another conversation: “I notice that when I make requests, you react aggressively. Is there something going on?” And I will learn more about the context of your response. That’s fostering connection.

A true connection needs to be based on truth.

Part 3 — Work

(12) Nathalia: In your experience, do you notice if there is a connection between having a hard time positioning yourself professionally, and also in our personal lives, in our relationships? Or are these different things?

Hermano Castro: No, they usually overlap in most aspects, and it relates to one’s personality structure.

The most validated personality theory today is the Big Five. The big five refers to the five factors that form our personality, and each one varies from 0 to 100%.

Each one of us will show a certain percentage for each factor. None of them is right or wrong. But each one presents advantages and disadvantages depending on the level you possess for each.

One factor is agreeableness, which means how much a person tends to consider the other’s problem as their own, and how much tendency they have to become submissive to others to avoid causing pain.

So, for example: Someone who has high levels of agreeableness, they may be very polite, and may fear being assertive because they don’t want to upset the other person.

On the other hand, when someone has low levels of agreeableness, they will have a tendency to be more competitive/direct, and may fall into being harsh and less empathetic.

There’s also a difference between genders, for both biological and sociocultural reasons. Studies have shown that women have a tendency to present higher levels of agreeableness when compared to men in general.

Someone who has a high-agreeableness trait might be afraid to be assertive because they worry that it will bother the other person, or upset them. And if this happens, the discomfort is so great that they tend to avoid it.

So, using this example in the clinical practice, when we identify these traits, we work on ways to help them express themselves in a more assertive way, developing a sense of self-protection because they usually struggle to negotiate on their own behalf.

The other side of it is not great either. People with low-agreeableness have a tendency to be more assertive and straightforward, but they will have to learn compassion and tact in how they express themselves if they want to connect better with others.

Our personality greatly influences our experience of situations, for example: if you put a high-agreeableness person in HR firing people, they might burn out quickly. A low-agreeableness person might thrive. Neither is right or wrong, it’s about fit.

(13) Nathalia: A common struggle that people share with me is that they can execute their work well but can’t talk about it or articulate their perspective. Do you have any insight on this gap?

Hermano Castro: Ok, so these are different skills. Just because I know how to do something well doesn’t mean I know how to communicate it well. Even on a neurological level, they happen in different areas of the brain. A great example of this is when we’re studying languages. Just because you understand a language well doesn’t mean you can speak it properly.

These are different functions. So, if one of these functions, for example the communication one, is not well developed in you, you can start training it. Instead of focusing on doing more of it, which won’t help in the communication aspect.

You have to set the right goal to work toward according to the area you want to develop.

(14) Nathalia: Nowadays, for autonomous professionals/entrepreneurs, communication becomes practically a business requirement due to the social media marketing aspect of growing a business or practice. How can someone who struggles with this start communicating without feeling like they’re “performing”? This is another struggle I hear a lot too, when people say they don’t feel like themselves. What’s your view on this?

Hermano Castro: Ok, there are many nuances here. Let’s explore the different layers. Performance isn’t necessarily bad. Right now I’m performing, but I’m performing appropriately for the context. If you’re going to show up in social media, you will perform at some level.

Performing doesn’t necessarily mean that you’re not being authentic, this is a trap we may fall into at times. For example, I like to use this metaphor to reflect on this: Water has three different states. It can be solid, liquid, or gas. And whatever state it is, it is still water.

The same applies to us. When I’m in a clinical session, I’m Hermano, the psychiatrist. Does this mean that I’m not being myself? No. I’m performing my psychiatrist facet authentic to the context.

I’m not Hermano the psychiatrist when I’m with my girlfriend or around my family, unless they need me to perform some aspect of my work. And even under this performance, I will still be authentic to myself.

Authenticity means to be connected with your essence.

For example, if you’re naturally shy or reserved but you force yourself to be a loud comedian online, you would be acting in dissonance with your essence.

It doesn’t mean that you cannot do that, but it means that doing so will feel heavy and uncomfortable.

Considering that communication is a tool for connection, and social media, in theory, exist to connect us to others, a good strategy then is to follow authenticity: show a facet that’s authentic to you so the right people can resonate. At some level, this helps people to identify with you.

If you offer people a performance that’s not authentic to you, you will end up attracting people who don’t really connect with you.

But back to the question, you don’t need to be on social media if you don’t want. It definitely helps as a tool to promote your work in the times we live in. But then you have to ask yourself: what is your goal? Why are you doing social media? To get more clients? To build partnerships? To become known? Once you have this defined, then you will understand what you want to express, and the more authentically you do so, the better you can position yourself, and the more connection you create.

Being authentic doesn’t mean oversharing. It means expressing something essential in a true way that enables connection.

Entrepreneurship becomes easier the more you know yourself because you will shape your business and make choices that match your personal traits and characteristics.

Part 4 — Internet

(15) Nathalia: I have followed you on Instagram for many years, where you always seem to have a consistent presence. What motivated you to start communicating on social media?

Hermano Castro: That’s an interesting question. I used to create content in a more informal way for a while, but I started taking my account seriously when I started psychiatry residency, when I was graduating as a psychiatrist. My main goal was to attract patients so I could launch my own private practice. But the reason why I think I’ve been consistent with it is because I always wanted to be a psychiatrist since I was 14 years old. I love this profession. And when I started the residency I was so excited about it, I wanted to learn everything there was to learn and my hobby was studying psychiatry.

I would devour books and get excited about what I learned. And I noticed “Nobody talks about this, I want to talk more about it.” So, I started making videos and it became like a study diary: I recorded connections I discovered and made videos about them.

In my perspective, the reason why I started creating this connection with my audience was because something about my enthusiasm resonated with them. It wasn’t something costly to me, or heavy, because it was an outlet for my own expression: I wanted to put reflections somewhere, organize my thinking, leave the learning recorded, and see how it landed.

I learned something almost daily and shared it, and it became a pleasure, especially because it worked.

(16) Nathalia: Did you ever worry about what people would think? Did you have any insecurities that many people feel when expressing themselves online, or did it always come from a place of expressing your enthusiasm?

Hermano Castro: Oh yeah, it always comes up. This also relates to some deeper aspects of personality. For example, I have low agreeableness, so much so that I became famous for my series “Loving slaps from the psychiatrist” (literal translation), where I reveal the real motivation or dynamic behind people’s messy situations they bring to me without sugarcoating it or protecting their feelings.

Sometimes I know that some topics will create controversy, and sometimes I even want that, I want to see what happens. I love it (laughs).

But sometimes it also becomes exhausting, because it’s common that people misunderstand you online. And even though sometimes I already expect to be misunderstood, sometimes I’m really surprised by how badly people misread things. But it’s part of the game. Even if you are super strategic, and approach any topic in the softest way possible, you still run the risk of being misunderstood at some level.

Depending on the personality, this can hit one person harder than it hits others. But this is something that is within your control. You can adjust the rhythm, how you handle it, and respect your limits.

And this goes back to knowing yourself.

(17) Nathalia: Do you think that social media sometimes create an illusion of self-expression? In the sense that people think they’re expressing themselves but are actually performing an edited version of what others expect?

Hermano Castro: It’s very tempting to fall into that trap, and it has a lot to do with your goals. What is the reason why I’m expressing myself through social media? Sometimes, you might have a goal you haven’t fully admitted to yourself yet — that you’re actually looking for mass approval.

Then you may express opinions that aren’t yours, because you saw they get praise. You might reaffirm other people or ideas because it’s what’s trendy even though you don’t really resonate with that. Or you might criticize something or someone who doesn’t actually hurt your values because the online masses are more likely to validate.

And it might even feel rewarding in the short term, but it’s not sustainable. Life happens in the long term. Eventually the mask falls, you contradict yourself, something true is revealed, and the contradiction is exposed.

People hate discovering they were deceived.

So, if you have the main goal of being approved by others, no matter what you’re doing or saying, not only in social media, but in life as a whole, it doesn’t work well as a long term plan. For example, I might pretend that I don’t like rock music so you like me, and in the short term you actually do, and I will feel that people in general like me for this. But then one day you catch me listening to rock music, and all our relationship was built on the fact that we didn’t like rock music. So now, that relationship is doomed.

A better goal, that we should cultivate, is to reveal who we truly are. Your authenticity will attract people who genuinely like you.

And even if you hold a belief that people would never like you for who you truly are, I usually bring the counterpoint of: it’s impossible to be hated by the whole world population. Even the maniacal serial killers receive letters from fans saying how much they love them.

There are always going to be people who will resonate with you, and others who won’t. You need to discover who they are, and to do so, you need to reveal who you are in truth.

I’m not saying this out of moralism, but from my clinical experience. I’ve seen hundreds of people who tried to employ these strategies, and all went wrong eventually.

(18) Nathalia: Ok, so here’s my last question: with AI being the “hot topic” of the moment, people who want to express themselves at times in their relationships, work, or online, they turn to AI first asking variations of the question “How do I say this?” or in the worst cases even “What do I say?”. We’re creating a habit of putting a machine between us and our communication. What’s your view on this? Is it ok? Does it harm our ability to express ourselves?

Hermano Castro: The main question here is: since we observed that this is happening. What is the cause that is leading this habit to take place?

I see this as a symptom of a generation that feels disoriented. “I didn’t learn to communicate well, I need to do so in this exact moment, but I don’t know how. Who can help?”

Sometimes you never even learned to ask for help, and the AI is there, it welcomes you, it reassures you always, it’s private (in theory), so you seek help.

I don’t see it as necessarily a problem if you’re using it as a tool for orientation and refinement. For example: “I want to decline an invitation. I was going to say: ‘I don’t want to go.’” AI might help you phrase it more politely like “Thank you so much for the invite, but I’m not available to go.” That can be healthy and teach you patterns. Now you understand how to decline other invitations in the future.

What I see as extremely problematic is when people use AI to delegate decisions. Like “Hey ChatGPT, that person invited me to go out. Should I go?”. When you do this, you are handing over the protagonist role of your life to an algorithmic machine.

There’s even the trend of “ChatGPT tarot” becoming an oracle. “ChatGPT, draw a tarot card for me so I know if you should meet that person or not.

Anytime we use technology to delegate decisions, it becomes a problem.

This is part of being human, it’s not like this never happened before. People try to do this with therapists all the time “Should I end my relationship?” If I answer this question for you, I’m robbing you of your life’s purpose.

If I tell you “yes, and it goes wrong, you will blame me; if it goes right, you don’t get the credit, it’s all because you followed what I told you to do.

So, the worst thing you can do is to delegate decisions, because anytime you do so, you undermine your own satisfaction. You will never give yourself the right merit for living a satisfying life, it will always be because someone else told you so. And that’s very sad.

So, whenever we are talking about AI, oracles, or people, it isn’t harmful if you’re using it as a tool, the real problem is when you delegate the power of deciding over your own life.

What did you think of the interview?? I would love to know what stood out for you!

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Resources & Support

• Dr. Hermano Castro's book Communicate like an Adult (Portuguese version).

• 📔 Get my Workbook - Reconnect with Your Authentic Voice: Guided exercises integrated with AI to find your voice and tell your story.

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We all want to hear that everything is going to be ok. Things will flow. We will get what we want. Then, moved by this desire of self-soothing, we reach for external things to us: Tarot cards, systems, seers. Whoever and whatever can tell us: “It’s going to be ok.” But what I’ve found for myself is the exact opposite. Every time I reached for external reassurance, I was actually giving my power away.

The feel-good trap and the trade-off you don’t see coming

I was 21 when I went to my first astrology consultation. My friend had visited this guy and said it was “life changing.” He told me about things that happened in my past, which I confirmed. He told me about the energetic moment I was going through, and hinted at some things in a broad sense that would happen in my future.

I was impressed that he could identify things I had experienced in the past, so I assumed that he was right about my future, even though I had no idea of what that looked like. Nonetheless, I left that day feeling really good. As if I knew more about myself than before, as if I was better prepared to deal with life. Even though, absolutely nothing changed. I didn’t change. Circumstances stayed the same.

Then, some time later, my mom told me about this aura reading thing she did and how incredible it was. So, I went and tried it for myself. As I sat in front of the woman with her eyes closed, she hovered her hands around me and started talking about all the colors she saw, and the flowers around me. She told me about how I was an old soul, told me about a past life, and the purpose of my soul in this life. Wow. What an experience. I left that meeting feeling so great and energized, nobody had ever said such nice things about me. I felt seen. Someone actually could see through me. But unfortunately, I went back to my life. And nothing changed.

Years later, I was going through a phase where I felt really stuck and directionless about my professional path. I was completely burned out from a job I could not leave. I wanted to move out from my home city, but didn’t see how. I cried often from the pain of the moment, and uncertainty of the future. Then, one day an older friend I looked up to (she was in her 50s, when I was in my 20s) told me about this man. She had a medium-sized company and clothing factory, and she said she didn’t make any decision without consulting him. Maybe I should talk to him. And so I did. Because I really needed someone to tell me that I would be ok.

I scheduled the meeting and arrived at his place. It looked precarious, in a really poor neighborhood. I remember looking around and feeling really weird about the energy of the place. But I couldn’t trust my feelings. I felt powerless in the face of life. I needed someone to tell me I would be ok. So, I sat in the chair in front of him, and he takes cards, and numbers, and stuff I couldn’t make sense of. He starts talking, interpreting what’s for me from all those objects and what he sees. Until he opened his mouth and the next thing I heard made my soul detach from my body into a profound state of numbness and freeze. He said I wouldn’t find love. And he said that at a time when the only good thing I had in my life was a relationship with a boyfriend. And he said that to someone whose most profound trauma and fear was being unlovable. That night, I was having a panic attack in my boyfriend’s bedroom. And I was triggered into a depression I had just recovered from a little more than a year ago. I went looking for perspective, expansion, and to hear that things would be ok. I left hopeless about every aspect of my life.

It took me many years and therapists to recover from that day. To actually make sense of what had happened. I went to a complete stranger to tell me what I should do with my life. I didn’t feel good when I met him, and still I stayed. I was retraumatized at a moment when I was feeling the most vulnerable. And the reason why it had that impact on me was because if I need other people to tell me things will be ok, I cannot take my power back when they tell me it won’t.

You might think that was my last time reaching for external guidance from complete strangers. It wasn’t. Most times, it’s not one situation that makes us rethink and learn more about ourselves. Most often it’s a series of repeated situations that happen until we say “ok, that’s enough. This shit needs to change.”

Our need to make sense of things

I know that astrology, tarot, human design, and other things are becoming more and more popular. So, we are also living in a world of more and more uncertainty.

What I used to hear about these systems, and I used to also repeat myself, is that they help us to learn more about ourselves and know ourselves better. After at least 15 years of experiencing life since the first time I engaged with these things, I found that not to be true.

You can’t learn about yourself from someone else. Most often than not, you’re being fit into a stereotype. You are having characteristics about yourself validated, so that you “accept” more of yourself and earn the right to say “but this is who I am.”

The way we learn about ourselves and how we are is by knowing how to feel our feelings, validate our inner experiences, and then analyze them. Why do I feel this way? How am I perceiving things? Do I like how this happened, or don’t I? What do I need now? What would I like to be different? And so on. The way we learn about ourselves is through self-inquiry based on our experiences and experimenting with different behavior to test new outcomes.

But these are hard questions to sit with most of the time. Especially when we don’t have the answer straight away. Or when we don’t trust ourselves. Or when we never learned to validate who we are and what we feel. It’s easier to go to someone else hoping to hear “Everything is going to be ok,” so you can feel good. At least for a few hours.

The real problem is that you don’t trust yourself yet

I remember when, in my early 30s, I discovered human design, and I started praising it for how it had changed my life. I was again, once more, deeply unhappy at a job, burned out (Hello, my own patterns), and beating my own ass up every day for not doing better. Then I learned that because of my human design profile, I needed to rest in between sprints (not surprising, right?). And from that day onwards, I stopped beating myself up and gave myself permission to rest.

Human design didn’t tell me anything new I didn’t know about myself yet. It just revealed how little I trusted myself with my own perceptions, feelings, and experience. I needed something external to me to tell me what to do.

The problem is that when you reach for these types of external guidance, you give all your power over yourself and your life away. And maybe you don’t feel like you have power when everything feels out of control, or facing pain and uncertainty. I get that. But you do, and sometimes the most powerful thing you can do is just to sit with your feelings, and fear, and uncertainty, and breathe. Let the waves move through you, or through the season of life you’re going through, until you can see things more clearly.

Anyone telling you about you or your life is still just another human. Another human with pain, with fears, with traumas, with limited understanding of life. There’s nothing that is said by anyone that doesn’t pass through their own filter and interpretation. Which makes it even crazier that we would trust other strange people to tell us how our life should be.

Looking back at my life so far, I know one thing for sure: Things change. Everything passes. Repeated cycles of pain come from repeating the same behaviors (most of the time unconsciously). When you change the way you act, things around you change.

I went through moments when I felt stuck professionally. When I experienced heartbreak. When I felt alone. When I had existential crises. The only thing I can spot in common among all those situations regarding what made me move past them is this: action and patience.

Act, even when you’re unsure of the outcome. Try something different. Show up differently around people. Break your own patterns. You will see so much change in life. But for this, self-observation, self-inquiry, and being able to be present with your feelings, including painful feelings, are required. Therapy also helps.

Things will be ok. Not because other people are telling you so. But because you’ve got yourself.

But honestly, this is what really made the shift in me

I practiced and studied Buddhism for many years, so one day I was at the temple, and I asked the monk: What is the Buddhism view of astrology?

He told me that astrology used to be used in the past by masters to have a sense of the karma of a group or civilization. Not for individuals.

And by karma I want to clarify that it doesn’t mean destiny, and it doesn’t mean something good, or bad. It means tendencies according to your actions. A simplified example for clarity: if you eat loads of sugar every day, you have a tendency to experience diabetes. If you are frequently generous to people, you have a tendency of experiencing people wanting to give back to you.

In direct translation from Mahayana Buddhism, karma is defined as “intentional action of body, speech, or mind that creates future consequences.”

The whole purpose of the Buddhism philosophy and meditation practice is that we can gain more awareness, self-understanding, and power to change our actions, in other words, our karma. Because when we change ourselves, our reality changes.

Which contradicts entirely the point of reaching for systems that reinforce a certain way of being, or aim to predict how our future will unfold, to hear that everything will be ok, when the power of making things turn out okay is within us.

Curiously, Sadhguru, a famous Indian mystic, who is known for having experienced enlightenment (I’m not confirming, just reporting), said several times: “astrology is guidance for fools”.

He argues that people who accept predictions about their life refuse to use their own intelligence. “An intelligent person cannot easily be predicted because they may act creatively.“ Astrology and other systems may describe influences, but living according to predictions means giving up your own intelligence and self-responsibility in life.

Which turns out that life proves it right. Remember that older friend in her 50s I looked up to, who had a company and wouldn’t make a single decision without consulting her guy? I learned a few years ago that her company broke. She was in debt with multiple other businesses and suppliers. Doing her best to avoid paying her debts.

Well, it seems like she handed her decisions to someone else for years. And when things fell apart, there was no one to hand that back to. I guess she never learned to trust herself. Or take real responsibility in life.

I think about that sometimes.

Warmly,

Nat

Have you ever left a reading, consultation, or session feeling great, but nothing actually changed? What were you really looking for?

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Mail club for self-discovery

If you enjoyed this piece, upgrade your subscription & join The Letters Circle , to receive a physical letter 💌 every month in your mailbox, with reflections and exercises to discover more about who you truly are. 📮

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It’s been a while since our last links I sent to my friends, so I bring you the compilation of the last two months <3

It has been a month since I arrived to live in the jungle of Costa Rica for five months this year, and while I absolutely LOVE the hot weather, the surf, and the tropical vibes… it has been quite an adventure to adapt to such a different reality from what I’m used to.

There’s no power or internet where I’m staying, so houses are powered by solar energy, meaning we can only connect power during the day. Internet is powered through Starlink (kudos to Elon Musk for this, it really works). And the closest town is 30 minutes of bumpy driving. It has only three streets and an abundance of coconut water (which became my motivation to endure the road) 🌴

Every little thing you take for granted in the city can be a mission here, and I’m very proud I managed to send the first letters of our mail club, where I shared more details about life in the jungle 🐒

But I digress. Let’s get right to the point. Here are the links I sent to my friends in December and January:

On the Self

You Can Do Anything You Want, You Are Bound by Nothing

For when you need a boost of inspiration to just go do the thing.

by

How to Get Whatever You Want

On how to ask so you can receive

by Jim Rohn

this will help you figure out what you want

On expanding your surface area for luck so serendipity can find you

by

Monthly (physical) letters for self-discovery

On creating a monthly ritual to reflect and discover more of yourself

by

On Communication

Being Nice Won’t Save You in Difficult Conversations

On how to be kind and assertive in conversation, instead of being nice and taken advantage of.

by Jefferson Fisher

The constant struggle to be articulate.

A reflection on the struggle of being understood and seen, making the interesting point that our difficulty communicating well might be less about finding the right words and more about our reluctance to take up space.

by

Personal rebranding is not what you think it is…

How to build an online presence that reflects who you really are and what to focus on at each stage of your journey

by

On Relationships

How I Manifested Better Friendships

On being intentional in ALL relationships so you can get what you give.

by Meehika Barua

How to fall in Love

On letting yourself be seen, so love can find its way to you

by

I hope you find some of these helpful!

And if you have any recommendations of links, please send me my way or share in the comments :)

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The letters Circle 💌 A mail Club for Self-discovery

If you enjoyed this piece, upgrade & join The Letters Circle to receive a physical letter with a self-discovery practice every month in your mailbox 📮

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Lately, I’ve received some emails from you sharing your stories. While it makes me really happy that you trust me enough to share bits of your journey, most of them finish with a similar ending: So, what do I do?

The series of emails took me back to the version of myself that, up to a few years ago, also used to ask other people: what should I do?

Since I've outgrown this habit, and my life has gotten much better for it. So here’s what I’ve learned about making decisions for yourself, and how it builds self-confidence and self-trust.

It’s not that you don’t know how to decide; it’s that you worry about what other people will think of it

I think that deep down we all know what we want for ourselves, but what often gets in the way of pursuing that is the fear of what other people will think of us. Will they think I’m choosing wrong? Will they think I’m a loser? Will they think I’m ungrateful? That I don’t care? Will they think this or that about me (fill in with fears in your mind)?

So, we don’t allow ourselves to truly focus on what we want and what matters, because our primary attention is going towards how it will be perceived by others. This can be your friends, your family, people on social media, and also no one but a projection of “others” as a faceless group that you carry on your shoulder or in the back of your mind.

Sometimes “others” are only one single person who you admire for some reason, and while they don’t spend one minute of their lives thinking of you, or knowing that you exist, you still wake up every day trying to prove yourself to them because of what you project in your mind about what they mean.

I made the “right” decision when I accepted a high-paying job years ago, only to find myself crying and drained at the end of the day. I also made the “wrong” decision when I decided to give a second chance to someone who had hurt me deeply, only to end up with the best relationship I could ever dream of.

I put “right” and “wrong” in quotes because those labels reflect how other people viewed my decisions at the time, not how I understood them myself. In both cases, I ultimately did exactly what I wanted. Still, I won’t pretend that external validation played no role: knowing that some people would see me as more impressive for accepting that job likely made it easier to say yes. Likewise, when I decided to give a second chance, I found myself second-guessing not because it felt wrong to me, but because I feared being judged as foolish if it didn’t work out.

One practice that has helped me decide when I get voices in my head is to sit with myself for 10 minutes and for this time being, remove any perceived opinion of others from the equation. That’s when you gain some clarity on what is left for you.

There’s no right or wrong decision, there’s only what is aligned in the moment

Other times, it’s not what other people might think that gets in the way, but the overthinking of all the potential outcomes of a decision, which leads to analysis paralysis.

In essence, there is no wrong or right decision, simply because we can’t foresee how things will play out. Sometimes, we just have to trust life. Also, labeling decisions as right or wrong means that you first have to answer: right or wrong for whom? and with what goals in mind?

The only right decision is the one that feels right for you in the moment according to your intentions, even if your intentions change later.

Eight years ago, I left Brazil for Europe with no plan, no network, and no money, but the little I had saved to cover basic three-month costs. Was that the right decision? Probably not in the eyes of most of my friends who were marrying, buying apartments, and getting promotions in their jobs. Probably not in the eyes of my parents who weren’t trying to stop me but were silently worrying about me “throwing my life away.”

But for me, I was thinking: what is the worst thing that can happen? I come back to have a roof over my head, and food on the table in my parents’ home, to the same friends I had for a lifetime, and the same work opportunities I already knew and didn’t want.

You know, if you start that course you always wanted but midway you decide you don’t like it, you can always drop out. If you move to a new city or country and decide that it’s not what you actually want, you can go back. If you quit your job to build the business you always dreamed of and it doesn’t work out, you can always get another job.

I think that so much of the pressure we put on ourselves that leads to overthinking is the perceived notion that whatever we decide, we have to stick with it for a lifetime. No, you don’t.

Very few things in life are irreversible. The only one that truly matters is death. I truly believe that besides death, there is so much possibility of workarounds no matter what happens, if you put your mind to it.

How making decisions helps you build more self-trust and confidence (no matter the outcome)

I made the wrong decision every time I decided for something that others thought was better for me but it went against what I wanted for myself in the moment. Just for the reason that I was betraying myself and giving little by little the power of my life for others to decide, which over time made me feel insecure in the face of life.

People might offer us things, or advice, and do things for us because from their perspective they believe that they are doing what they think is the best for you.

But the only person who can possibly know what is best for you in the moment is you, even if it turns out with an undesired outcome.

Because in that moment you’re learning to think for yourself, and part of learning also means that you will get things “wrong” sometimes. Which is very very very important in the process of learning to trust yourself and backing yourself no matter what happens.

One of the reasons why I used to ask others what to do because I was scared I couldn’t handle things if they didn’t go as planned. Most of the fear wasn’t about practical outcomes. It was about emotional ones. Later in life, I discovered that it was because I didn’t know how to feel my feelings.

That’s why training yourself to make decisions (by deciding!!) along with building the emotional capacity to stay with what arises is the best way to build self-trust and confidence in yourself, no matter the outcome, because after many repetitions, you will know that no matter what happens you will be ok, because you got yourself.

It doesn’t mean that you can’t consult people you trust on their perspective and opinion. I still do it multiple times. What changed is that now, before I ask a friend or a mentor what their view is, I already have my own opinion formed for what I want. And I use others’ perspective as a way to notice what feels right for me.

Another important point to add is to be aware of who you are asking an opinion from. Everyone shares their perspective through the lens of their own fears, traumas, values, and desires. While the point is not to be constantly looking for self-validation, be sure to talk to people whose discernment you truly trust, and feel aligned with decisions they have made for themselves.

I can’t tell you enough about times when I felt deeply insecure and would share my troubles with anyone who wanted to listen, which only served to get them trauma dumping on me, and fucking with my head even more.

Direction makes decisions easier

I heard from a psychologist one of these days that people struggle to make decisions in their lives, like staying or leaving a relationship, job, country, etc., when they don’t have a clear vision of the life they want for themselves.

A vision doesn’t need to be specific to its core, but it needs certain direction. A great way to find direction is to think about your values, aspirations, and dreams. Once you have it laid out, it’s easier to decide what feels right and aligned in the moment. Even if it changes later.

Warmly,

Nat

I'm curious, tell me: what's your way of making a decision when you feel stuck or unsure?

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The letters Circle 💌

If you enjoyed this piece, subscribe & join The Letters Circle to receive physical letters 💌 with self-discovery practices every month in your mailbox 📮

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One day, when I was 15, my mom handed me the envelope that arrived for me in the mail. I was confused because I never received anything in the mail. I wasn’t old enough to pay bills yet.

When I opened it, sparks were popping inside my chest of anticipation, while I pressured the corners of my mouth to contain the big smile wanting to come out so my mom wouldn’t ask me too many questions.

My best friend had gone to live in New Zealand for a year, and two months had passed since she left. In my hands I held the 5 pages handwritten letter with rich details about her new life, the experiences she had, the people she met, and her perceptions of such a different way of living.

I couldn’t believe how cool was that. Because yes, we had email at that time, and also Skype for calling through the internet. So receiving a letter felt quite unexpected.

Especially after I realized that she had to:

• Think about me

• Make time to sit and write

• Make it look nice and cute (she did!!)

• Go physically to the post office and send it across the world

All of this to reach me.

For some reason, the letters, even though they took a month to reach me and another month to reach her, made us feel close to each other more than ever video call ever did.

It wasn’t just the letter or its contents, but each time I received a letter from her, I turned into a ritual. A moment to sit with her words and be present.

There was something about holding her words in my hands that made them feel more real, as if they could reach something deeper in me.

In four days, I will be leaving Portugal to live for five months somewhere in the jungle of Costa Rica. I have no idea where I’m going, although I heard it’s beautiful there.

My boyfriend was invited there for a work project, and I’m joining along. I’m excited, but I also worry about feeling isolated after building an engaged social life here in Portugal. Which brings me back to those letters from New Zealand. if physical connection mattered then, maybe it matters even more now.

Sure, chat apps, social media, and video calls are always there, but for some reason it doesn’t feel present enough.

That’s when it clicked for me: It seems like this is the perfect moment to go back to the old ways of connecting with people. Through the joy of physical things.

What if I create a letters circle?

I invite you to join the letters Circle

Each month, I will send you a physical letter 💌. Something you can hold, reread, and return to.

I’ll be sharing reflections about building inner authority, and developing self-trust, and one practical exercise in each letter that helps you develop deeper inner clarity.

I hope this becomes a monthly ritual for you to slow down and reconnect with yourself, as it will be for me while writing them to you.

Okay. Feeling excited? Me too! So, how does it work in practice?

1. Join the Letters Circle by upgrading your subscription.

2. You will receive an email with a form to share your mailing address.

3. Letters will be mailed every 17th of the month, or the next working day.

4. You’re welcomed to write back to me, or share your thoughts directly in the chat/email!

This feels like an exciting experiment, and you know how big I am on experimenting with things that bring us joy. I hope that this excites you as much as it does me, and I can’t wait to send you the first letter.

Subscribe now

Warmly,

Nat

Did you ever have a letter, a postcard, or a note that stayed with you longer than any text ever could? When was the last time you received something in the mail that actually made you feel something?

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I was in a beach parking lot, handing out samples for my newly launched smoothie business. I was about to get in the car and go home when my business partner said, “Wait, there are three guys standing by the van… let’s just do one more round and we’re done.”

So, I walked to them and said, “Hi! We’re a new smoothie business in town… would you like to try some samples?” They were excited, they liked the taste, we took photos, we posted on Instagram, and I went home. What I didn’t expect was that my DMs would get busier after that promotional post. But not necessarily because of the smoothies.

The texter (one of the guys of the van) was not only showing up in my DMs, but as if by magic, he seemed to be everywhere I went in town. After a few weeks of multiple “coincidences,” or better said, pursuit, he finally asked me on a date.

He was fun, cool to talk to, and I felt physically attracted to him. He was kind and attentive, but after a month seeing each other, I told him, “Don’t expect anything from me, I only want to be friends.”

Something about him didn’t quite click: he clearly expressed his intentions, he was very communicative, and he was available at all times. He was different from anyone else I had dated before. Which made my brain get to the obvious conclusion: I have to run away.

Over the following months, it was a cat-and-dog game. He continued to text me, somewhat a bit intense for someone who was a friend. I continued to hang out and surf with him, somewhat confusing for someone who is not interested. Occasionally, he would drop in a “joke” about wanting to be in a relationship with me, and I would become meaner over time, saying things that would break his heart, in an attempt to push him away.

“I’m being honest, I don’t feel anything for him”, I said to a friend one day who insisted that we would be great together.

I thought my friends were crazy, and I started to get really annoyed with them. “How come they don’t see me? How come they don’t listen to me? I don’t feel anything and I cannot make myself feel things if I don’t!”

One day, months after that first date, I am in a therapy session when my therapist stops me in my tracks: “Wait, Nathalia, I think there might be something to look at here. You keep mentioning this person, but you say you’re not interested. Your actions and words don’t seem to line up. Do you think we should take a closer look at this?”

“No! For the last time, I’m telling you: I don’t feel anything for him. Just leave it,” I replied to her and moved on.

Just after that session, out of the blue, he texts me saying that he’d be picking me up on Friday for a surprise weekend trip. My first thought was: “Are you crazy? Why the hell do you think I’m going on a trip with you?”

My second thought was: “You know what... this just might be the perfect opportunity to show my friends and my therapist that I’m not unwilling! I will be able to finally prove to everyone that even though we’ll spend all this time together, I still can’t connect with him.”

To fall in love with anyone, do this

I was committed to proving it hard. So much so, that a few weeks back, I had come across a New York Times article called To Fall in Love with Anyone, Do This.

The article talked about a study made in the ‘90s by a couple of psychologists about a series of experiments that resulted in 36 questions that were said to foster intimacy, closeness, and love between people. “If a science-backed experiment can’t make me have feelings, nothing can,” I thought.

As we were driving to our weekend destination, I casually said, “Hey, do you want to play a game? I found these questions online and we can kill time on the road,” hiding the intentions of my scientific experiment. And so, for the next two hours, we went through each one of the 36 questions one by one, alternating answers. When we arrived at the destination, I was proud: “See, I was right all along… I’m still not in love.”

Unfortunately for my ego, things had changed when he dropped me home two days later.

How I kept myself safe from love

Years ago, before I met him, I made an unconscious decision: love is not safe. Relationships became somewhat of a game to me, one that as long as I didn’t allow myself to feel, I would be okay.

Of course, I wasn’t aware of that at the time. If you had asked me, I would tell you that I genuinely wanted to connect with someone at a deeper level, find companionship, love. But in practice…

I would ask prospects all the deep questions, silently analyzing their patterns, their traumas, showing up as the “emotionally aware and conscious,” but deep down what it actually gave me was a sense of control. As long as I knew all about them, and they knew enough about me, I was safe.

But during that two-hour drive to an unknown destination, I got distracted. The questions nudged me toward what I had resisted this entire time: to be seen.

In between harmless questions like “what would you save if your house caught fire?”, and “Would you like to be famous?”, there were questions that revealed parts of ourselves we don’t always want to be in contact with, “What is your most terrible memory?”, “How do you feel about your relationship with your mother?”, and “Complete this sentence: ‘I wish I had someone with whom I could share...’.”

For those who decide that love is not safe, the real fear isn’t betrayal or being hurt. It’s that, if it does break, it will sound too familiar. As if it were only confirming something we’ve known for a long time. That it was never meant for us in the first place.

So I stayed guarded. Until those questions caught me off guard.

I didn’t see it coming

The questions didn’t make me fall in love, but they opened a door to let love pass through. I wasn’t just being seen. I was also seeing him. I entered his mind, but this time I left the psychotherapist’s glasses and notebook outside. I listened to how he thought, what shaped him, what he valued.

Those conversations kept unfolding throughout the weekend. By the time I was back home, I felt attached, something I only realized after he had left, when I began to miss him.

What those two-hour car ride taught me was that real connection isn’t made of sparks at first sight but of willingness to enter someone else’s inner world while inviting them into yours.

It seems that the science people know something, after all.

Warmly,

Nat

36 questions to fall in love

1. Given the choice of anyone in the world, whom would you want as a dinner guest?

2. Would you like to be famous? In what way?

3. Before making a telephone call, do you ever rehearse what you are going to say? Why?

4. What would constitute a “perfect” day for you?

5. When did you last sing to yourself? To someone else?

6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

7. Do you have a secret hunch about how you will die?

8. Name three things you and your partner appear to have in common.

9. For what in your life do you feel most grateful?

10. If you could change anything about the way you were raised, what would it be?

11. Take four minutes and tell your partner your life story in as much detail as possible.

12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

13. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?

14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

15. What is the greatest accomplishment of your life?

16. What do you value most in a friendship?

17. What is your most treasured memory?

18. What is your most terrible memory?

19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

20. What does friendship mean to you?

21. What roles do love and affection play in your life?

22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

24. How do you feel about your relationship with your mother?

25. Make three true “we” statements each. For instance, “We are both in this room feeling...”

26. Complete this sentence: “I wish I had someone with whom I could share...”

27. If you were going to become a close friend with your partner, please share what would be important for them to know.

28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

29. Share an embarrassing moment in your life.

30. When did you last cry in front of another person? By yourself?

31. Tell your partner something that you like about them already.

32. What, if anything, is too serious to be joked about?

33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

35. Of all the people in your family, whose death would you find most disturbing? Why?

36. Share a personal problem and ask your partner’s advice on how they might handle it. Then, ask your partner to reflect on how you seem to be feeling about the problem you have chosen.

Tell me, I'm curious: What's one way you protect yourself from being truly seen? Or have you ever pushed someone away because they felt too safe?

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If you want to find your voice and build a brand that reflects who you are, check out my other newsletter: Diary of a Brand Therapist.

Read my latest piece there:

Diary of a Brand Therapist by Nathalia Montenegro

Personal rebranding is not what you think it is... (self-assessment inside)

A year and a half ago, I rebranded myself. But not in the way that you’re thinking…

Read more

4 months ago · 18 likes · 1 comment · Nathalia Montenegro

Hello hello, today is December 3rd... omg.

Last time I had the mind space to send the “Links I sent to my friends” it was in September about links I sent in August!! Crazy. These past 3 months flew by.

In October I had my family visiting for a month, which was the best time, and also a time that exhausted me to the core, as I was trying to juggle work, content creation, and optimizing for spending the most time possible with my family. Not easy.

When November came, I fell sick (the overload bill always comes later). And I kept telling myself “next week everything will be back to normal” as I tried to catch up with all things I postponed for after my family left. On top of that, I just moved places, and discovered that everything always takes more work than we suppose in the beginning.

And today is December 3rd, and I might just give up the idea of being on top of my to-do list that just gets bigger day by day.

So, yeh, excuse my little ramble, but I felt like I needed to add some track record here for my future self if I ever come back to this and ask “Why did I skip 3 months of links?”

So, let’s dive into 12 links I have to share with you :)

Self

1

On why expressing who we are to others is a prerequisite to finding the love we seek.

Speak so you can be found

By

2

On why self-expression is the foundation of fulfillment and of manifesting the life you dream of.

This is how you actually manifest the life that you want

By

3

On a better system than the "let them” theory for decision making.

The “Most Days” theory

By

4

On the inner tension between freedom and belonging, and how we usually mistake “freedom to” for “freedom from.”

Freedom isn’t the absence of commitment

By

5

Astrology lovers, don’t take this personal, but this is a beautiful piece on responsibility and how it helps you take the reins of your own life instead of outsourcing your power.

Astrology is a drug!

By

6

On how to use AI combined with filed notes to gain a broader perspective of who you are, how you’re showing up, and to readjust toward a direction that feels meaningful for you.

The practice that turns self-discovery into self-direction (prompt inside)

By

Career

1

On the most pressing questions that came from identifying your top pleasures at work, and how to navigate career change.

The 12 Points of pleasure at work - Part 2 (Q&A)

By

2

On the top lessons from running a service-based business for over 10 years, as I failed and bounced back multiple times along the way.

5 Things I got wrong about running a business (and how I fixed them)

By

Communication

1

On the direction social media and our content consumption behavior are converging towards. (I found it very insightful!)

Everything Is Television

By

2

On how to express yourself through personal essays in a way that connects with others on a human level.

The Beginner’s Guide to Writing Personal Essays

By

3

On dealing with self-doubt and trusting what you have to say.

How to find what only you can say

By

4

On practical strategies to build your brand behind the scenes while keeping your day job

How to build your brand when you can’t be seen

By

I hope you find some of them helpful!

And if you have any recommendations of links, please send me my way and share in the comments :)

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I’m not a religious person, but growing up in a catholic family and having gone through biblical studies as a kid made two or three of those stories to stick with me. This was one of them.

After having studied at little bit of multiple religions along the years: catholicism, hinduism, buddhism, spiritism… and being skilled at pattern recognition, I formed the opinion that in essence they all converge to the same thing through different stories or metaphors that fit better each specific culture where it was originated.

What interests me in these stories isn’t whether they’re literally true. It’s the metaphor beneath them: creation starts with expression.

So, when the bible says we are like God, and when God speaks he/she creates, it also means that when you speak you create your reality.

There is so much advice out there around manifesting the life you want: writing down on a paper, in your journal, making rituals, setting intentions.

I started manifesting the life I wanted not when I was in a room in silence, but when I started speaking what I wanted and acting in coherence with my message. It’s incredible the things that happen when you position yourself. Life literally responds to it.

People who speak for themselves suffer less

When you don’t speak for yourself, you’re not just misunderstood. You block the very process that shapes your life.

I saw this quote the other day in a book by the psychiatrist Hermano Castro:

People who communicate better suffer less. This is not an opinion, this is a fact. They suffer less because they can make themselves better understood. Because they can solve better their own problems. Because they can through communication, make allies, ask for help, require direction, give instructions to others to do what they need to be done, express their will, and communicate their intention and plans.

The moment you reduce that friction, life has room to respond to who you really are.

When we don’t express ourselves with clarity and intention, we will consciously or unconsciously use different strategies to express or compensate for our needs and wants. Most of these strategies fail.

We will try to be “the good person”, we will burnout ourselves at work, we will become passive aggressive, we will dramatize, we will attack others, and at the end of the day, we will feel that life is unfair to us because we didn’t get what we wanted.

When you don’t speak for yourself and communicate, you struggle in every area of your life:

• You feel invisible in your own relationships because no one knows what you actually need.

• At work, you never negotiate your compensation or let others get credit for your ideas, then feel bitter watching others advance.

• You don’t build your brand, and your business struggle.

• You choose careers or life paths based on what sounds impressive to others, not what you actually want.

And the list goes on…

These aren’t random frustrations. They’re the outcomes of a life you didn’t choose, because silence lets other people choose for you.

I know this in my skin because although I’ve worked in communications for my whole life, I used to not speak my voice. I used to feel invisible, catering to everyone’s need but feeling behind. I resented other people who did similar work and had visibility. I remember thinking to myself that I could do better than them, that it wasn’t fair that they were seen but I wasn’t.

I’m going to confess something… deep down I wanted to be “discovered”, like if someone from the outside would come and notice how amazing I treated people around me, how nice I was, how great was my work (have you heard of “I’m going to let my work speak for itself?”).

Waiting to be discovered is the opposite of manifesting. It’s outsourcing your voice to chance.

Communication is agency, and there’s no manifesting without agency.

What happens when you start manifesting your life

When I started speaking my voice, it was like I entered a new reality: my relationships improved. My friendships became more solid. I started working with brands I admired. I tried new projects. Some worked, some failed. I learned from all of them, which gave me a whole new set of skills and experience.

I started publishing and showing up online to build the community I always dreamed of. My clients trust me more because I say no more often. I’m honest when I think something is shitty or won’t work. I bet on bold ideas more often.

I can’t think of a part of my life that hasn’t improved since I started intentionally speaking for myself.

This is what I mean when I say speaking creates your reality. When you stay silent, life happens to you. When you speak, you shape it.

Speaking didn’t just fix my relationships. It shifted my entire trajectory because it made my inner world visible to the outer one.

I remember one moment when I stopped to reflect for a second.. and I thought “oh shit.. I’m manifesting this”. Yes, because I was vocal and specific about what I wanted to others. Not because I wrote on a piece of paper, and hoped it would come true.

You only get what you want in life when you express yourself.

But more importantly: when you don’t speak for yourself, you’re being dishonest with others. But especially with yourself. Let me explain:

When you don’t say what you think, other people misunderstand you. Worse, you start confusing yourself. You wear a mask so long you forget your real face.

When you stop hearing your own voice, it gets harder to trust what’s going on inside you.

And the question left is how can you manifest the life you want if you’re not honest with yourself?

What’s stopping you to speak for yourself

Before I understood this in my bones, life showed me what silence cost. Only a few years ago, multiple parts of my life collapsed. Work, relationships, community. Like when all the planets align but in the opposite way you’d expect.

That was a moment when I thought I had lost everything… and what followed next was that I finally started speaking my voice. After all, what is left to loose? I wasn’t scared anymore.

This was not overnight, it was a long process but I committed to it. My nervous system was not used to having me speaking for myself, so every single time I did.. it felt too much, it felt scary, it felt as if I was doing something wrong.. but now I was not interested in being perceived as the ”nice” person anymore. And at every chance I had to say my truth it got a little easier and a little easier.. until it became the default.

The point is: up to that moment I had never integrated or embodied the fact that I could be true to myself and still have everything I wished for.

But the whole point is that you can only get everything you wish for when you’re true to yourself.

And what seemed crazy at the time is that piece by piece all the parts of my life started to get back in place: work started flourishing, people I though I had lost got even more closer, friendships became more solid, others drifted apart, new people came in.

And when I reflect back there was one thing that stopped me from speaking my voice: FEAR OF WHAT OTHER PEOPLE WOULD THINK OF ME.

Which is a direct result of not trusting yourself.

We tend to operate under the logic: if “others” (insert the names in your head here) think of us as “good”, “perfect”, etc = we will get what we want.

My question is: how that has been working for you?

If it hasn’t been working so well, maybe it’s time to change the strategy.

But another common thing that stands on the way is: Most people think they know themselves, but when you ask them what they want, they freeze. Or they repeat what everyone else says they should want.

When you spend so much time adjusting to what others want, you loose touch with your own voice. You learn early to prioritize others. To be agreeable. To not rock the boat. You get rewarded for it. You become easy-going, flexible, low-maintenance… but in truth, you’re not low-maintenance. You’re just nullifying yourself.

When you mold yourself to fit whatever the situation requires, you lose access to what you actually think, feel, and want.

You can’t speak your truth if you don’t know what your truth is.

Silence is not a communication issue, it’s a creative one.

It stops life from responding.

How to discover your truth, start speaking for yourself, & Manifesting your life

If you want to reconnect with your truth and speak for yourself, there’s a process I’ve used over and over in my own life. It starts with your story, moves into your body, and ends with the patterns that shape what you believe.

The practice that was most helpful for me was to own my story. All the parts of it. The ugly, the boring, the failures, the wins, the big moves, the small moves, my roots. Rooting everything I say in my own experience. Our your lived experience isn’t a matter of opinion. It’s how our identity is formed.

If you’ve been reading Dear Self for a while, you’ve probably noticed that this is exactly what I do in every post: I write my story, then I explore a subject, an insight, a point of view rooted in what that experience taught me.

And that’s the point: your story is the raw material of your truth.

Once you write it honestly, without polishing or performing, you start seeing yourself differently.

From there, don’t stay in your head. Pay attention to how each part of your story feels in your body. Some parts feel light. Others feel tight, heavy, or strangely distant.

Your body will tell you which parts you’ve accepted and owned, and which ones you’re still processing, and which parts you’re ashamed of (here’s where your work lies). Owning the parts you reject means integrating your identity instead of fragmenting it.

Those sensations matter, because your story isn’t just what happened. It’s the meaning you gave each moment. Meaning is what shapes the way you speak, what you ask for, and what you believe you’re allowed to want.

And once you understand the meaning, your patterns start to reveal themselves: the loops you’ve lived through, the challenges that keep repeating, the situations where you shrink, the ones where you rise without effort. Patterns are just repeated meanings. When you see them clearly, you will stop confusing them for fate.

When you know your roots, your story, your body’s truth, your meaning, and your patterns, your voice stops wobbling. You stop performing and start expressing. And that’s when life finally responds to you, not the version of you you’ve edited for everyone else.

A tree only grows strong once its roots go deep.

Go deep and own your roots, so you can grow rooted in yourself.

Maybe this can help too

I recently launched a workbook, on my other Newsletter, Diary of a Brand Therapist, to help people who want to express themselves and build their brand online but are stuck in the “I don’t know what to talk about” or “I don’t want to sound like everybody else”.

But the feedback I’ve been getting has been unexpected in a positive way.

• One person said “this helped me at the perfect time, when I needed clarity and connection to my purpose“.

• Other said “I have discovered really deep things about myself that i haven’t realized until now. It’s like being on a therapy session. I already started noticing patterns and ideas that come up often”.

• And another said: “I feel a deeper connection with myself and what I find important right now and I feel I can articulate that better now.”

It’s a process that guides you through exercises to dig into your story to reconnect with your voice.

So, I thought that maybe this can also help people who want to discover more about themselves, and not only those who want to build a brand.

If this is you, you can get the workbook here:

Reconnect with Your Voice

Warmly,

Nat

What’s one moment in your life when speaking your truth changed something for you?

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If you enjoy this post, make sure to subscribe

Subscribe now

If you want to find your voice and build a brand that reflects who you are, check out my other newsletter: Diary of a Brand Therapist.

Read my latest piece there:

Diary of a Brand Therapist by Nathalia Montenegro

How to find what only you can say

I heard this quote in 2018 as I listened to a podcast, and it never left me…

Read more

6 months ago · 16 likes · 5 comments · Nathalia Montenegro

One of them took a deep breath, moved her eyes around as if in search of an answer, and finally said: freedom.

The moment she said the word, it was as if I was now sitting in front of my younger self.

She was much younger, probably around her mid-twenties. She had recently moved from her country of origin to Portugal; she used to have a traditional job, and now she worked remotely. She talked about how she wanted to move around freely and get to know people from all corners. She wanted to feel free, but she couldn’t say what freedom looked like.

I felt it in my chest. But I didn’t think it was my place to tell her.

She would have to figure it out for herself, just like I did.

The Search for “My Place”

When I was in my 20s, I had a plan. I would travel the world until I would find “my place”. But my idea of finding this “home” meant jumping from city to city, and never committing to people or places, because doing so would hold me back from finding “my place”.

I wanted to find a place to belong but I also wanted to be free. I had this idea that happiness meant doing whatever I wanted, whenever I wanted, going anywhere I wanted without constrains. I imagined that once I achieved that state, I would feel happy and fulfilled. I also thought freedom was an emotion.

I never felt like I belonged in the place that I was born. Which was exactly what pushed me to go out and explore the world and nurtured my drive for finding “my place”.

Today I know why I struggled to find my place: no matter where I went, there I was.

Freedom to belong

I wanted the freedom to be myself, but deep down I was afraid that attaching to others would take that freedom away.

So I kept searching for the right place or the right people where I could finally feel like my full self, yet I never stayed long enough to find it. I was stuck in a cycle.

I used to think that belonging meant conforming to expectations that didn’t align with who I was. I believed that to belong, I’d have to lose myself. And yet, I craved connection the way humans crave water. That tension led me into some really bad situations — in friendships, love, and work — where I tried to earn belonging at the cost of my own truth.

The obvious conclusion my younger, naive mind came to was that the way to avoid pain, and to stay free, was simply not to commit.

What it really means to belong

I wish I could say I knew what I was doing when I found my way out of that cycle. But I can only be grateful to life for having created the conditions that forced me to sit with myself. Literally.

I had been in this village for a year, and I was ready to move on to the next place.

So, I bought a ticket to Switzerland. But the day before my flight, my lawyer called telling me that getting on that plane would jeopardize my visa process, something I’d been waiting so long to sort out.

A month later, I booked another flight ticket to Italy. But COVID restrictions were put in place, and it stopped me from traveling once more.

A month after that, now for the third time, it was time to go to Hungary. But then a job opportunity came up that I couldn’t walk away from, and for the third time, a major force intervened that prevented me from leaving the city and the country I was in.

By that point, I was crying, angry and frustrated. I felt trapped, as if life itself is keeping me from being where I’m meant to be. I don’t even know where that place is yet, only that I’m being kept from finding it.

One day, while walking on the beach with slumped shoulders, empty eyes, and a heart full of questions, I had to cross some rocks. I walked over them trying to keep my balance, and bang I twisted my foot. Now, I couldn’t walk.

I had tried everything in my power to leave that town, and now I couldn’t even leave my apartment.

It was on a Sunday morning, having breakfast with friends — me doing the usual, complaining about life and how unfair and stuck I felt — when a friend looked at me and said:

“I’m not a spiritual person, but I have a friend in Norway. And if he was here listening to you, he would say that maybe the universe is trying to tell you something.”

I don’t know what happened in that moment, but suddenly something clicked. In a split second of time, I saw everything different. That made so much sense.

All I was trying to do for the last months was to be somewhere where I was not, and every single time life pulled me back. I resisted and fought so much, that it got to the point life needing to break my leg, so I could stay still.

And so I did. From that conversation onwards, I decided to accept that I was not going anywhere for a while, the world was closed, there was nowhere to visit, and I needed to heal my foot.

A few months earlier, I had met a guy who was very clear that he wanted a committed, serious relationship with me. But despite liking him, I had told him to expect nothing from me because I wouldn’t stay. I would leave to go traveling and find my place.

During these past 6 months before I twisted my foot, we had multiple conversations where I would tell him all the ways why we wouldn’t work out, and he kept telling me all the ways why we would. This guy had seen my worst. I had handed him a list of all the ways I was broken. And somehow, for reasons I couldn’t understand, he was still there.

But now, with my new setup, me locked in an apartment because I couldn’t walk, made me stop fighting life. I relaxed and started being present with what I had around me. I decided that there was nowhere to go for a while..

With the space I had created when I allowed myself to settle — even if just for a while — I start growing into that guy, and into that town, and into the people who lived there.

Two months after that Sunday breakfast, my lawyer called me saying that my papers were finally released. I have a Portuguese passport, and I’m free to go anywhere I want. But now, for the first time in my life, there’s nowhere else I want to go.

This year, I celebrate five years with that guy and six years since I arrived in that town.

And I finally understand that what I was looking for was never a place.

Commitment as liberation

A lot of things had to come together at once for that shift to happen. One of them was starting therapy again (by accident), with a therapist I randomly found. That’s where the real work began: learning to trust myself, to commit despite fear, to stay even when staying felt hard.

Because of the myths we often hear about what liberation looks like, I need to make something clear: it wasn’t that guy, place, or community that “saved” me. What saved me was my own choice. The decision to stay committed, even through the hard moments in therapy, in relationships, in community, and in this town.

In this journey I’ve been on over the past six years, what I realize now is that freedom is the ability to choose what to commit to — to stay, to build roots, to show up authentically with all our parts. Commitment doesn’t mean you’re trapped; it means that you have decided.

As I reflect, I realize that every decision comes with responsibility — and taking responsibility is frightening when there’s no self-trust.

But the truth is, there’s no real freedom without responsibility. You have to stand by your choices. Not deciding isn’t freedom. It’s a trap you build for yourself.

I have committed to a person, to a place, to my work, to a community. And I’ve never felt more free because I know each one of them was my choice.

The trap of endless options

One of the biggest illusions that keeps us from commitment is the trap of endless options. I know I fell into that trap for a while.

We often think that waiting for something “better” is about what’s in front of us — the job, the place, the person. But in truth, it reveals much more about how we relate to ourselves.

When we avoid commitment, we also avoid being seen. We mostly perform — trying to be the admirable one, the good one, the impressive one — while losing touch with who we really are.

As long as we keep our options open, we can hide behind possibility. It feels safer that way; we don’t have to risk showing our full selves.

When we notice the flaws in someone or in a place and immediately start imagining that there must be something “better” out there, what we’re really doing is resisting our own imperfection. We’re unwilling to accept or reveal the messy parts of ourselves.

Underneath it all, there’s a fear that choosing means closing doors forever, that commitment might lead to unbearable regret.

True belonging

What I didn’t understand back then was that belonging has nothing to do with finding the right place. It’s about being comfortable enough with yourself that you can show up as yourself.

For years, I thought I had to choose between either be myself or belong somewhere. I believed that attaching to people or places meant I’d have to shape-shift into whoever they needed me to be. So I kept moving, convinced that the right place would be the one where I could finally be accepted without having to “fit in”.

But I had it backwards.

I wasn’t going to belong anywhere as long as I kept hiding who I was. And I couldn’t commit because I didn’t trust myself to handle what came with that choice, the joy and the disappointment, the comfort and the conflict.

What I would tell me younger self

If I could sit in front of my younger self, just like I sat in front of that girl in that networking dinner, and tell her only one thing, this would be it:

“Freedom isn’t the absence of commitment. It’s choosing commitment without fear of losing yourself.”

If you could tell your younger self one thing about freedom or belonging, what would it be?

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If you want to find your voice and build a brand that reflects who you are, check out my other newsletter: Diary of a Brand Therapist.

Read my latest piece there:

Diary of a Brand Therapist by Nathalia Montenegro

Instead of building a brand, find your voice

Estimated reading time: 8 minutes…

Read more

9 months ago · 58 likes · 4 comments · Nathalia Montenegro

Self

• On the things they should teach you at school but they don’t - a short practical guide to emotional awareness

  How to actually sit with your feelings

  by

• On doing uncomfortable things for a easier and better life: rejection, learning to learn, and loving low status.

  How to be more agentic

  by

• On the importance of underthinking to keep momentum & achieve your dreams

  Literally just do things

  by

  

• On why you shouldn’t use AI as your therapist

  The Deadly Rise of AI Therapy Chatbots

  by

  

Communication

• On exactly what to say ask to make small talk enjoyable.

  How to Get Good at Small Talk, and Even Enjoy It

  by Harvard Business Review

  

  ---

  Career

• A quiz to help you discover what you actually enjoy about the work you do (or don’t).

  How to Discover What You're Actually Good At - The 12 points of pleasure at work.

  by

  

• On why finding your voice is exactly what allows you to connect with others, be seen, and create aligned opportunities.

  6 signs you haven’t found your voice yet

  by

  

• On how important it is to see tangible results from your work to feel fulfilled at work

  The death of the corporate job.

  by

  

• On the importance of surrounding yourself with internet-sharers to share your work.

  How to share your work online

  by

  

I hope you find something helpful!

And if you have any recommendations of links, please send me my way and share in the comments :)

Leave a comment

Subscribe to get the links every month straight in your inbox :)

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So, I did my best to reply as thoughtfully as I could to every single comment I received. But the questions kept coming: “What’s next?”, “What do I do with this?”, “What jobs align with these pleasures?”.

Then, I tried to help indirectly by sharing a practice that has helped me to develop self-awareness and make more aligned choices, with hopes that maybe this could help people find their own answers.

But still, the comments and questions kept coming, and over 100k readers later, this message reached my inbox:

“(..) I was wondering if you’ve written more about the choices you made afterwards, or if in general you could share how your life and career have evolved.”

And at that moment I realized that while I don’t think of myself as qualified to give other people career advice. I’m definitely qualified to tell my own story and what has worked for me.

I made peace with it, and here we are.

Since there’s much to cover, here’s an overview what you’ll find:

• What happened after I discovered the career workbook

• How I went from feeling lost to find meaning with the power of experiments & having some faith in life

• Q&A from part 1

  • 1. What specific jobs or careers are related to these pleasure points?

  • 2. I’m stuck, what do I do next?

  • 3. What if I can’t go back to college?

  • 4. How to decide what you want to do for the rest of your life?

  • 5. What if you’re on your 40s, 50s, 60s..?

• How I practically aligned myself with my points of pleasure

What happened after I discovered the career workbook?

In part 1, I told you that I was feeling miserable at work, considering going back to university to change careers entirely, when I came across the career workbook that made me realize that maybe I didn't have to change careers after all. Now, 3 years later, I feel happy and fulfilled at work.

But it wasn't that straightforward. It never is.

A few months after I had discovered the career workbook, I was blessed with a lay-off.

I had been wanting to leave for a while, but I didn't have the self-esteem to do it. Because even when you need to quit things, it requires a minimum of trust and confidence in yourself.

The day after I was laid off, I remember waking up in the morning, walking to my balcony, and looking around the shared garden of my building. For the first time in months, I could breathe. I was amazed by the colours of the plants, the sound of the birds, and for once in a long while, I was present.

Now, with space, I started slowly remembering who I was. Out of the 12 years I had been working in my field, 8 of them were as self-employed. So, I didn't go looking for another job.

But I did feel lost. The reason why I had accepted that role was because I was not happy being self-employed anymore back then.

It had been just after COVID, and I was feeling very isolated and disconnected from the world. I had also made a bad business decision some time before that, which made me resent the way I was operating my business and the kind of clients I was attracting.

So, I thought that joining a team and a company in a field I was excited about would bring me the fulfilment I was looking for. As you already know, it didn't. So, yeah, I felt lost.

But, in retrospect, I’m grateful for that job. It was not all bad. I did learn a lot, I did achieve things I'm proud of, and worked with people I admired. But most importantly, I'm grateful because it was a different experience for me, and it helped me to learn a lot more about myself.

It was an experiment.

The power of experiments & having some faith in life

Up until that point in my life, I had exclusively worked with corporate brands. But right before I was laid off, I received an unusual inquiry for work. A therapist from New York reached out wanting to work on her own brand and communication.

I showed up to that call ready to tell that we weren’t a good fit. But the conversation flew so naturally that we ended up agreeing on a project. Her goal was to learn how to tell her story and amplify the reach and impact of her work. Working with her helped me rediscover my spark and motivation in ways I didn’t remember I had.

Helping her improve her communication also meant that she could make her life better, as well as, the life of the people she helped through her work. That’s when I realized that I love working with people, instead of for people. (it’s not an accident that I score high on the pleasure of helping others).

That was another experiment.

After that, I started taking notes on what excited me, what peaked my curiosity, what I liked, and didn’t like, and started trying new things on that direction.

That's how I applied on a whim to work with The Diary of CEO team (!!!) by replying to a post on Instagram. I thought I would never have a chance with so many people flooding their DMs, but less than a week later, I ended up being one of just two people they were considering to lead the project.

I was so taken by a mix of disbelief and excitement by what was happening that I completely bombed in the last interview because I couldn’t stop saying “I’m such a big fan! I listen to every episode! I’ll will do anything you want me to do!!” and wasted every precious minute of that call that I could have used to talk about what was actually important: the project.

Anyway, that was another experiment. I kept taking notes of what excited me, and moving in that direction. By the way, this newsletter was born as an experiment.

And that’s how, with a lot trial and error, and observation and adjustment, I gradually found my way back to work I enjoy doing.

If you’re interested in learning more practically about how to adopt the experimentation mindset, I highly recommend the book Tiny Experiments from the neuroscientist Anne-Laure Le Cunff, she shares her personal journey from quitting the “dream job” at Google, feeling lost on what to do next, and discovering she wanted to study neuroscience.

For me, experiments it’s one part of the equation. You have to try things to discover how you feel about them. But there’s another part of the equation, which is having some faith in life’s wisdom.

In short, it comes down to 3 points:

• The more clarity you have about yourself and what you want, somehow life starts bringing you more of it.

• Events and experiences in life are not all good or bad. Everything is information and feedback. That doesn’t mean that life won’t suck at times. But if it sucks, at least use this information to do something about it.

• And no, we can’t predict what will happen, and what is the “right” path, the opportunities that will come, or the problems that will show on the way. Unfortunately, or not, we have no control in life. But what we do have control over is to learn about ourselves, who we are, and try to make decisions aligned with that, and then have some faith that life will gives us what we need to grow.

Q&A from part 1

1. What specific jobs or careers are related to these pleasure points?

Pleasure points don't mean a specific job or career.

It doesn't work this way.

There is no formula for the perfect job. Here's how it works:

Pleasures, in the way that the exercise in the book frames them, have more to do with the "how" than the "what." For example:

Similar career, different pleasure points

My best friend, , and I work under the umbrella of brand & marketing. But while some of my top pleasures are understanding & self-expression, some of his are making money & creativity.

Which means that he crushes at everything e-commerce, sales channels, experimenting with buttons, and systems. The pleasure of making money is not about being driven by the money itself, but it's about figuring out what moves or tactics will make the numbers change on the screen.

Me, on the other hand, I love understanding identity and how to communicate it in a way that connects emotionally with other people.

Whenever we have the chance to work together, it's like yin and yang flowing in perfect alignment. Because our skills and pleasures complement each other so much. So, although we both have careers in the same field, our focuses are different because our points of pleasure are different.

Different careers, similar pleasure points

My boyfriend and I have similar pleasure points at work: we both score high on creativity, but we have completely different careers. While I work in communication, he builds things — like physically. From houses to retail experiences.

People often confuse creativity with self-expression and beauty. After all, we were taught that painters, sculptors, and musicians are the creatives. But creativity is about problem solving.

I score high on creativity because I see every client and project in front of me as a puzzle to be solved (understanding), and the puzzle has to be put together in a way that serves a specific goal (creativity).

My boyfriend scores high on creativity because he sees every project as a Lego challenge to be solved, and he also scores high on the pleasure of making money, which for him means anticipating the needs of people and projects even before they can realize it themselves.

People shared in the comments

Someone shared how much they loved their work as a programmer and how it was no surprise that they scored high on understanding, technology, and order.

There were people who reported scoring low on creativity, even though they worked in "creative" fields, but the same people also reported high scores on self-expression. Which maybe means that they love to create to express themselves, but not to use this expression to solve problems.

For example, you might love to paint, but you want to paint what you feel like painting, and not what other people want you to paint.

So, no, there are not specific areas of interest or work that fit specifically each pleasure point. The pleasure points are the "how," not the "what."

2. I’m stuck, what do I do next?

If I were feeling stuck, here's what I would do.

Based on the points of pleasure I identified, I would:

1. Reflect if there's a way of incorporating tasks, or shifting focus, in my current work that would fulfil more of the pleasure points.

2. Additionally, or alternatively, I would make a list of interests I have, and things I'm curious to learn more about, that I assume resonate with my points of pleasure.

3. I would go to YouTube, or some educational platforms like Coursera, Skillshare, etc., and take short free or paid courses in those interests, and learn some basics about things I'm interested in. Some of them will pique my interest more than others.

4. Then I would cross some off the list, and would keep learning about the things that made me the most excited.

5. Once I know a little more about one or two things that I'm interested in, I would start projects to apply what I'm learning myself. Depending on what it is, I could do it by myself, or offer to do work for someone else.

6. Now, with real practice, I have even more feedback about what I'm interested in, what I like, what I don't, and what I see myself working on.

7. If I'm really excited, I would push myself to improve, and do more of it. And that's how I would start figuring out something new. You never know what possibilities will find you along the way, unless you start.

This is not only what I would do if I were feeling stuck, but it's actually what I did when I was feeling stuck.

I got super curious about behavioral science and started studying it on my own. It was during this time that I was also considering going back to university to become a psychotherapist.

I went pretty deep in both worlds. I dropped behavioral science first. I loved the psychology behind it, but I really wanted to work with people, not engineer user and consumer behavior.

Then later, while I was still contemplating the idea of a psychology degree, I discovered the science and art of storytelling, which made me feel pulled to do more and more of that. So, I didn’t change careers, I leaned in discovering what pulled me.

The best part is that this journey added some pretty cool tools and knowledge to my toolbox. Nothing is disposable.

Just keep in mind that, you don’t figure out things by thinking, you figure out things by doing.

Here’s a great article to help you act:

Useful Fictions

How to be more agentic

I often hear agency talked about as if it’s an inherent trait: Either someone has it or they don’t -- in which case, too bad, they’re doomed to a life in the minor leagues. This hasn’t been my experience. Over the years, as I’ve gradually grown dumber relative to my peers through a combination of aging and making smarte…

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2 years ago · 3121 likes · 114 comments · Cate Hall

3. On going back to college

I know we all come from different realities, and different "worlds". For some, going back to university is just a decision away, for others, it’s something that sounds completely out of possible reality.

But unless you want to do something on the academical path or that requires you to have a license, for example like being a doctor, lawyer, engineer, or dentist, you don’t need to go back to university to change careers, or explore new paths.

Coming from someone who has two university degrees in different areas, I can confidently say that everything worth knowing I learned after I graduated and stepped into the real world. The problem with academic curricula is that they're made for perfect-world case scenarios, which rarely happen in the real world.

In many ways (not in all ways) college stopped serving people a long time ago. It's not a prerequisite anymore for finding a career or making money. I really believe in the power of the internet—there's so much we can learn for free. And real expertise doesn't come from a degree but from real-world experience.

4. How to decide on what to do for the rest of your life.

You don’t.

Nowadays, research shows that Millennials are likely to have 3-4 different careers in their lives, while Gen Z may transition between 5-6 careers.

Having one career for life feels like a boomer legend. Even among the boomers I know, some are already on their second careers.

You're under no pressure to pick one thing for the rest of your life. You're allowed to change your mind. You may find something you love in this moment of your life, and this might change in 10 years, because you grew and evolved as a person. And that's ok.

I wrote more about this here:

5. Finding a new path on your 40s, 50s, 60s..

Multiple people ranging from 27 to 55 years old shared that they worry it's too late to redirect.

I believe that much of what we think is possible for us, or not, is a reflection of the references we have about what is possible for other people. Unfortunately, for many decisions about our own lives, we may feel we need permission from others. And other people stories give us just that.

So, if you would like to change but you're scared that it's too late, please go to ChatGPT and ask it to find as many examples and stories as possible of people who made a career change around your age and became successful in it.

I, fortunately, have many examples in my own family. My mom graduated as an engineer, worked in the public sector for most of her life (not as an engineer), and decided to become a lawyer in her late 40s. I remember how terrified she was of going back to the classroom and sitting beside 18-year-old students. In her 50s, she was an intern at a law firm. I'm so proud she did it. She has no idea how much permission to follow my truth she gave me when she decided to follow her own.

My aunt was an occupational therapist who painted and sold art on the weekends in the markets. In her 40s, she decided to study interior design. She loved it so much that afterward, she went back to university to pursue a 5-year degree in architecture. We shared the same graduation ceremony. Today, almost 10 years later, she is one of the best architects in my city.

I also recommend you to check out this insightful article from Rachel Lawn — I'm sure it will inspire you:

Micro Shifts & Life Lifts

I just started training for my dream career at 52 (and what nobody tells you about being "too late")

I've just handed in my written work for my first year of psychotherapy training. I turn 53 next month…

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a year ago · 492 likes · 93 comments · Rachel Lawlan

It's only too late when you're dead.

So, how did I practically aligned myself with my points of pleasure at work?

I still work doing brand strategy and communication. I'm still self-employed, which gives me the freedom to shape the direction and approach of my work as I like. But this is what I changed based on my points of pleasure at work (understanding, self-expression, creativity, helping others, teaching, and independence):

• I shifted my focus to work with people who want to create and amplify their own brand, either professionals or founders who have emotional connection with the story of their business. Instead of working with more corporate brands.

• I made 1:1 sessions the core of how I approach my work, so I can spend more time interacting with people — it turns out that every single client tells me "I look forward to every session, this feels like therapy." (After all, it seems like I didn't need to become a psychotherapist to help people communicate their truth).

• I shaped my approach to work to lead with personal truth and story, and build the business strategy around that foundation.

• I made a pact with myself: I will never ever shift, mask, or dilute parts of myself to increase any chances of being hired or close a deal.

And this is what every piece of newsletter I write is about: authenticity in your life, work, and business. Because what a sad life it is to live someone else's life, and not yours.

— But remember, none of this is advice.

Please, let me know if this helped :)

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If you want to find your voice and build a brand that reflects who you are and your unique body of work, check out to my other newsletter: Diary of a Brand Therapist.

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Diary of a Brand Therapist by Nathalia Montenegro

Instead of building a brand, find your voice

Estimated reading time: 8 minutes…

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9 months ago · 47 likes · 4 comments · Nathalia Montenegro

Estimated reading time: 7 minutes

You'd think that we learn from bad experiences. Unfortunately, this couldn't be much further from the truth.

Up until my 33rd birthday I had experienced 3 severe burnouts at work. Both when working for others and when working for myself.

So, no, I cannot blame external circumstances alone for my inner experiences. It seems that, I, have to take responsibility for myself.

I never saw it coming, until it was too late. I feel like I never had the chance to adjust the direction or pull on the brakes. I was in full automatic mode.

"I will never let this happen to myself again," I promised the last time. But now, I was about to dive into that hole again — If it wasn't for ChatGPT.

Reading the excerpt of my chat, you might think I'm suffering with impossible demands that I hate. But no, in this case, it is the other way around. I've never been so invested in all the things and people I love. But my pattern is to know no boundaries.

I get so excited and stimulated by the things that I'm doing that I just want to push through — to the detriment of my own sleep, nutrition, rest. "Why do I need to rest when I enjoy what I'm doing?", because if I don't, soon I will hate it.

And it won't be the first time to happen.

The method that saved me from repeating patterns

I started this practice two months ago, and it transformed how I see myself. A combination of journaling and AI, that results in self-awareness on steroids.

I’ve been more aware of my patterns of communication, I’m learning which relationships fill me up, and how. It has helped me adjust my focus to things I enjoy most, learn about my challenges from a different perspective, and provided practical direction and tools to change them.

In my last piece, about the 12 points of pleasure at work, I received many comments saying "this was so helpful," but they were often followed by the question "but what's next?". I noticed how people want definitive answers, a quick resolution, a step by step map to the impossible: life.

For the answers you seek, there's no map, there's only your inner compass. You follow it, you experience it, you get feedback from life, you adjust the direction. And you keep doing it again and again.

Whatever you're trying to figure out—career, relationships, yourself—this combination of tools will help you align with your inner compass much faster. It will reveal your next steps based on direct feedback from your own experiences.

Self-awareness is where real change starts, and the life you dream of begins

We're all stuck in patterns we don't see. The difference between a life you hate and one you love comes down to awareness-based choices.

Self-awareness is like turning on the light. It helps us spot what's holding us back, reconnect with what we really want, and design a life that feels more aligned.

When we catch these patterns as they happen, we can respond differently—creating the kind of change that leads to a life we actually want to live.

AI partner in self-awareness - How it works (field notes + AI)

I discovered journaling was a way to regulate myself, to reflect on my experiences, to channel away feelings that I didn't know how to process. But I often forgot to document the good parts of my life, the discoveries, the little things in my day-to-day, the positive encounters, the joys.

It wasn't until I discovered the concept of field notes, from Anne-Laure Le Cunff, combined with the power of AI, that I fell in love with the practice of journaling. You won't see me missing a single day entry.

Field Notes

I used to think of journaling as a moment of my day I put aside to write down whatever thoughts I had going through my mind with no specific goal or outcome. Field notes provided me with a different framework: to write a few lines throughout the day to audit and record the experiences I'm having.

• How I'm feeling in the moment (just a few words)

• What I'm noticing

• What's on my mind

• Who I encounter and how it makes me feel

• What I'm working on and what I feel/think about it

• Things I do, and how I feel or what I think about it

I don't have to write 5 pages. I just need to jot down a few words to record what I want to notice. It feels more like a self-study rather than writing a memoir.

It looks like this, but way messier:

You can read more about field notes and self-anthropology here.

AI super power

When you combine field notes with the superpower of AI, pattern recognition, you can notice your own patterns, challenges, and highlights happening in the moment.

AI reveals patterns you miss: emotional triggers, blind spots, recurring behaviours that shape your decisions.

It's like studying yourself and using real data to inform the direction of your next steps.

Pattern Mapping: Self-awareness in practice (My specific process)

An excerpt from one of my weekly analyses of my journal:

I had been suffering with body/muscle pain for weeks, and even though I went to see a physiotherapist a couple of times, it wasn't getting better.

It wasn't until I saw this report from ChatGPT that I realized that the muscle pain started on my second week of overstimulation and sleep disruption. What I thought to be a consequence of a bad day at the gym was actually my body saying: "you're not ok, you need to get some brain recovery."

I was also reminded that conflicts I had in that week in my relationships were a result of me not communicating clearly what I needed and then resenting the other person for that — an old pattern that tends to show up when I'm feeling more emotionally vulnerable.

I also gained more insights on things I should pursue more, and things I should leave behind. Noticing my patterns of energy and how they influence every area of my life has also been game changing.

This is how I do it:

1. I journal every day throughout the week — sometimes I skip a day, and then I do it in retrospect. I often do it in the evenings and/or in the mornings; I mostly forget to do it along the day.

2. I like to journal with pen and paper — but you can do it however you prefer, using notes app, Notion, docs, or whatever works best for you.

3. On Sundays, I digitalize my weekly entries using the app Whisper (it turns voice into notes). I read my weekly entries out loud to transcribe them. This is a step you won't need if you journal digitally, but it's a step I've come to appreciate.

   Reading my entries aloud helps me review the week's events, often giving me fresh perspectives and reminding me of details I might have otherwise forgotten.

4. Then once I have the transcript, I paste it into ChatGPT to get an analysis highlighting:

   • Themes of this specific week

   • Key events

   • Challenges

   • Insights

   • Recurring Patterns from Previous Weeks

   • To reflect moving forward

   The key in this process is to make sure that AI only reflects back to you what you wrote and avoid having it interpret or advise on any matter.

Use this prompt I created:

PROMPT

Note: Keep all entries and analysis on the same chat. This allows you to map patterns across the weeks.

WEEKLY JOURNAL ANALYSIS PROMPT

Based on the journal entries I’m sharing below, please analyze my week using the following structure and tone:

1. Start with:

   • What were the themes of this specific week (broad threads that shaped the overall week).

2. Break down the week into these 4 categories. For each, include:

   • Key events (what happened)

   • Challenges (if any)

   • Insights (reflections, learnings, awareness shifts)

     (Only include what’s actually mentioned or clearly reflected in my writing. Please don’t make up content to fill space.)

   • (1) Relationships & Social Life

   • (2) Work & Creativity

   • (3) Energetic & Emotional Patterns

   • (4) Personal Growth

3. What quotes & insights I shared to reflect on.

4. Recurring Patterns from Previous Weeks

   • Format:

     Recurring Pattern How it showed up again this week

5. To Reflect Next Week

   List 2–4 concise, relevant reflection questions based on what came up this week.These should help bring more clarity or intention to the areas that felt unresolved, repeating, or in transition.

Use clear, direct language (not corporate or formal), but keep it structured and reflective.

Avoid interpreting or giving opinions — just reflect back the content and what’s evident across time.

Important boundaries: This is not AI therapy

The key for a fulfilling life is self-responsibility. And you can't have that if you're outsourcing your life decisions to family, friends, your therapist, astrologist, tarot reader, or AI.

In the last years, I'm discovering that the sense of living a meaningful life comes not from perfect decisions, but from owning your choices and trusting you can handle the outcomes. The only way to do that is by discovering what feels right for you.

I should clarify something important: this isn't AI therapy, and that distinction matters.

Here's why AI can help with self-awareness but can't replace human therapy:

1. What creates real change is the emotional breakthroughs we experience in sessions by having our experiences witnessed by another human — reaching our amygdala (where our automatic responses and emotions live).

2. AI only reaches our frontal cortex, the logical rational part. It is often self-affirming, which makes you think that your perspective of the situations you encounter is accurate. This is often distant from the truth.

3. Most likely, the reason why many of us need therapy is because of the pain we experience in relationships with other humans — which is precisely why it takes another human to help heal these wounds. This is the essence of therapy: being truly seen and developing a safe, trusting bond with another person.

So, while I don’t recommend using AI for therapy, I totally recommend using it as a way to map your own patterns and studying yourself. You can even bring your insights to therapy (if this is the case for you).

This distinction matters because I've learned the hard way that outsourcing responsibility—even to well-meaning helpers—keeps you stuck in the same patterns.

Warmly,

Nat

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If you want to find your voice and build a brand that reflects who you are and your unique body of work, check out to my other newsletter: Diary of a Brand Therapist.

Read my latest piece there:

Diary of a Brand Therapist by Nathalia Montenegro

6 Signs You Haven't Found Your Voice Yet

Estimated reading time: 7 minutes…

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8 months ago · 7 likes · 4 comments · Nathalia Montenegro

There's a sort of pain that I experienced that I could never really describe despite my best efforts: something about having your real talents put aside, while being under-resourced and under-supported, to deliver what's being asked — from people who are clueless about what they themselves are looking for.

The problem when you're in this place — disconnected from work you actually enjoy — for too long, is that you might start losing your sense of self. Your work identity. You don't know which direction to aim when there are no clear parameters for what has to be accomplished — besides other people's opinions.

Which is the perfect recipe for having you question your own self-worth. "Will I ever be able to do anything good with my life?" — I asked out loud, multiple times, at some point of my downhill journey.

That's when I came to the mistaken conclusion that, despite working in the field for 9 years at that time, I wasn't cut out for it. I was in the wrong line of work, and I had to change my direction entirely.

I was ready to go back to university and pursue a psychology degree — until I came across this book: The Career Workbook, from The School of Life.

The Career Workbook

For the first time, in almost a year that felt like an eternity, I started considering that maybe it wasn't the work that was the problem, but the environment where I was executing the work.

The book helped me create my own criteria for fulfilling work—what makes me thrive, what challenges excite me, and what to seek out.

Misalignment can make us doubt everything we know about ourselves. The only antidote is deeply understanding who we are, which enables us to translate our inner compass into meaningful decisions and directions in the external world.

Many exercises in the book transformed how I saw myself, but one in particular helped me see myself through a new lens and gave me the vocabulary to articulate the pain I had been feeling but couldn't express. This was the exercise on the 12 points of pleasure at work.

The 12 points of pleasure at work

As kids, we're asked 'What do you want to be when you grow up?' and while we might give answers like I want to be a pilot, a vet, or tv show host, we never really think about what in this kind of work we might actually enjoy.

Without self-awareness, our interests can be highly influenced by the collective perception of a certain occupation, shaped by media narrative (Hello ‘The Devil wears Prada’), perception of status, and money expectations.

And the 12 points of pleasure at work leads us to reflect about what in the work that might give us pleasure and gratification, at least a minimum to keep us engaged.

Instead of asking ourselves who do I want to be? We can start getting to know ourselves by understanding our pleasure points, and then find the jobs which we can have the most pleasure.

So, next time you’re looking for your next occupation or job position, instead of looking only to the technicalities of it, look at it as a constellation of pleasure points. This is how you find an occupation that makes you say “I love my job”.

12 points of pleasure at work - Self-assessment

I took the information in the workbook and how they describe each point of pleasure, and turned it into a quick self-assessment test to make it more fun and interactive for you.

The point here is to rank in order of preference from 1-6 what are the pleasures that speak the loudest to you. This then becomes your inner compass.

Rate each statement from 0-2 points based on how much it resonates with you:

• 0 = Not at all like me

• 1 = Somewhat like me

• 2 = Very much like me

Add up your points for each category to identify your top sources of pleasure at work.

1. The Pleasure of Making Money

□ I get excited when I correctly guess what people need before they ask for it.

□ I notice inefficiencies everywhere and think about how they could become business opportunities.

□ Making profit feels like an intellectual challenge - solving problems others haven't noticed yet.

□ I enjoy understanding clients' needs better than they understand them themselves.

□ Generating money through my insights and solutions gives me genuine satisfaction.

Total Score: ___/10

2. The Pleasure of Beauty

□ I notice when things don't look quite right - misaligned buildings, poor font choices, cluttered spaces.

□ As a child, I loved activities like carefully wrapping presents or decorating my schoolwork.

□ I appreciate when everyday objects are well-designed and harmonize with each other.

□ I get more excited than others when spaces (like hotel rooms) have great aesthetic details.

□ A nicely set table or beautiful presentation makes me genuinely happy.

Total Score: ___/10

3. The Pleasure of Creativity

□ I love the moment when all possibilities are open - like having all the LEGO pieces spread out before building.

□ I often imagine how my favorite songs, stories, or experiences could be improved or different.

□ I enjoy thought experiments: "What if we tried this approach?" or "How could this be better?"

□ I'm always trying to find more effective ways to convey information or solve problems.

□ People mistake my love for better solutions as simply wanting novelty for its own sake.

Total Score: ___/10

4. The Pleasure of Understanding

□ As a child, I asked lots of questions because I wanted good reasons for why things worked.

□ I love when chaotic information suddenly makes sense through a clear, simple explanation.

□ Writing or reflecting helps me think more clearly and reduces my anxiety.

□ I get frustrated when people don't explain things properly or leave mysteries unresolved.

□ I enjoy news reports that go behind the scenes to explain the "why" behind events.

Total Score: ___/10

5. The Pleasure of Self-Expression

□ As a child, I loved when adults asked for my opinion and I had something to say.

□ I get frustrated when people don't listen - I want to make them pay attention.

□ I love sharing things I'm passionate about with others and seeing their reactions.

□ The idea of being interviewed or writing about my experiences appeals to me.

□ I feel most fulfilled when I've genuinely "touched someone's soul" with my words or ideas.

Total Score: ___/10

6. The Pleasure of Technology

□ I'm fascinated by how things work - machines, systems, even simple tools like pencils.

□ I love asking "What's the essence of this problem and how could it be solved more efficiently?"

□ I think we're still at the beginning of solving human needs through better technology.

□ I appreciate when tools are perfectly designed for their function, whether high-tech or simple.

□ I see technology everywhere, not just in computers but in well-designed socks or furniture.

Total Score: ___/10

7. The Pleasure of Helping Others

□ As a child, I loved being asked to help with tasks because it made me feel useful.

□ I enjoy it when friends tell me what's bothering them, even if I don't have perfect solutions.

□ Work feels meaningful when I know it makes a difference in people's lives.

□ I like hearing about the positive consequences of my work in others' experiences.

□ In games or stories, I was drawn to rescue scenarios and helping characters in trouble.

Total Score: ___/10

8. The Pleasure of Leading

□ I liked being in charge not for status, but for the chance to implement my ideas.

□ When others panic, I find myself getting more focused and clear-headed.

□ I enjoy it when people turn to me for advice and want them to trust my judgment.

□ I believe leadership should be earned through competence, not just given.

□ I dislike people who actively try to avoid responsibility when it's needed.

Total Score: ___/10

9. The Pleasure of Teaching

□ When someone makes a mistake, my instinct is to help them understand the right way.

□ I love the feeling of turning someone's confusion into confidence and mastery.

□ I enjoy filling in gaps in other people's knowledge when they're genuinely interested.

□ I remember teachers who recognized when I was really trying, even if I got things wrong.

□ I have to be careful not to come across as patronizing when sharing what I know.

Total Score: ___/10

10. The Pleasure of Independence

□ I love being alone with my thoughts - boredom rarely troubles me.

□ I get excited by stories of people who quit conventional jobs to follow their own path.

□ I prefer forming my own opinions about books, art, or ideas rather than following crowds.

□ I recoil from guided tours and group activities where I can't set my own pace.

□ An evening alone gives me energy because I can think and plan without interruption.

Total Score: ___/10

11. The Pleasure of Order

□ I like everything to have its proper place - chaos makes me uncomfortable.

□ I get annoyed when people tell stories by jumping around or forgetting important details.

□ As a child, I was careful about making my work neat and organized.

□ I enjoy sorting things into categories and reducing complexity to simple, clear systems.

□ I'm fascinated by how individual elements can be organized into larger, coherent patterns.

Total Score: ___/10

12. The Pleasure of Nature

□ I can't stand being in buildings where the windows don't open - I need fresh air.

□ As a child, I loved getting close to animals and imagining what their lives were like.

□ I enjoy outdoor challenges, especially when the weather isn't perfect.

□ Watching nature documentaries makes me want to be there experiencing it, not just observing.

□ I find being in natural settings energizing rather than just relaxing.

Total Score: ___/10

Your Results

Rank your top 6 pleasures by score:

1. ______________(Score: ___)

2. ______________(Score: ___)

3. ______________ (Score: ___)

4. ______________ (Score: ___)

5. _______________(Score: ___)

6. _______________(Score: ___)

Your top six results, can point you to the direction of the precious zone where your talents and pleasures meet the need of the world.

Discovering work that feels fulfilling is a journey. It is not straightforward but a journey that requires lots of experimentation. As we evolve, what once felt fulfilling might no longer satisfy us — that's why the answer to the question "who do you want to be?" is more of an ongoing discovery rather than a one-time definition.

What happens when you move according to your inner compass

Fast forward three years after that day I first opened that book, I never changed careers, but I changed my format of work, clients, and boundaries, so it all points to one direction: matching as much as possible the pleasure points that speak the loudest to me: understanding, creativity, self-expression, and helping others.

And what seemed impossible then has become my reality now. Feedback that comes with the words: "you're so valuable to us."

Warmly,

Nat

PS: I wrote a follow up on this post to answer many questions people shared in the comments. Here’s the link:

I'm curious to know what results show up for you in the self-assessment. Let me know in the comments!

Leave a comment

If you want to find your voice and build a brand that reflects who you are and your unique body of work, check out to my other newsletter: Diary of a Brand Therapist.

Read my latest piece there:

Diary of a Brand Therapist by Nathalia Montenegro

Instead of building a brand, find your voice

Estimated reading time: 8 minutes…

Read more

9 months ago · 2 likes · 3 comments · Nathalia Montenegro

Every other day I'm sending a link of something I read/heard/watched to a friend that results in interesting conversations.

So, here they are for you, links I sent to my friends last month — from AI, to writing, building better relationships, finding your voice, and discovering new ways of staying creative in a world of endless consumption.

I hope you can get a thing or two out of it!

Relationships

• On the importance of (and how to) having difficult conversations & dealing with resentment in relationships

  How to Get What You Want Every Time: 3 Steps to Negotiate Anything With Anyone

  

  by Mel Robbins Podcast

  ---

• What I learned about friendship from moving to a new country with zero connections.

  How to make friends as an adult

  

  by

  ---

Communication

• On the importance of lived experiences and connection as a differentiator

  How I Stopped Worrying About AI and Learned to Value My Humanity

by Every

• For anyone who wants to sharpen their writing, and especially enjoyable for those who write in English as a second language

  On Writing Well: The Classic Guide to Writing Nonfiction

  

  by William Zinsser

  ---

• On how to find your voice, and why that is your differentiation

  Instead of finding your niche, find your voice

  

  by Nathalia Montenegro

  ---

• On how to combine multiple interests and build an ecosystem

  How I'm building my brand with multiple interests

  

  by Nathalia Montenegro

Identity

• A different way of journaling that actually helps you learn about yourself

  Self-Anthropology: Become your own anthropologist with personal field notes

  

  by Ness labs

Creativity

• On consumption fatigue and how to become more interesting and creative. For those who love to cultivate parallels and new connections between your different interests.

  Creating a digital garden to end my doomscrolling

  

  by Anna Howard

I hope you find something helpful!

And if you have any recommendations of links, please send me my way and share in the comments :)

Leave a comment

Warmly,

Nat

Estimated reading time: 6 minutes

I was fed up with feeling lonely. Six months earlier, I had moved to Portugal with no plan and no connections. For the first time in my life, I was faced with the question: how do I make friends?

I remember in kindergarten, where I made most of my friends in Brazil, that I would just walk up to another kid and say: "Do you want to be my friend?" and with a simple "yes" from the other child, friendships of a lifetime started unfolding.

I come from a big city, Fortaleza has around 4 million people, but it just so happens that we don't live in cities, we live in bubbles. And in my bubble we used to say "Fortaleza is an egg," because everyone knows everyone.

When I left Brazil, at the age of 27, I had around 5 friends in the 'ride and die' category, 20 really close friends, and many acquaintances with whom I could enjoy familiar conversation if I crossed paths with them in the streets.

What I didn't realize until moving abroad is how little effort we have to put into forming bonds while growing up in our hometown. Back home, friendships happened automatically. My parents knew other parents, we kids played together, went to the same schools. Trust came built-in.

This was not the case when I was living in Lisbon in 2018. Lisbon is kind of a small city, with half million people, but I had no bubble, which made it feel huge. I was 6 months in, and despite having made a few acquaintances, I had no friends.

When I first arrived there, I met a girl who lived in the shared apartment I moved to. She cracked jokes, asked thoughtful questions, and made me feel welcome. So, I thought “I think we can be friends.” What I didn’t realize is that as I was moving in, she was moving out.

The story we tell ourselves about other people

As winter approached, my feelings of loneliness intensified. Multiple times I thought of reaching out to that girl and what stopped me from doing so was the story I had in my mind:

“She must be busy with her life or having the best time with her friends. Who has the time or interest to hang with someone like me who has no friends. What a loser I am.” I thought this regarding anyone whom I found remotely interesting.

But one thing I also knew: so far, I had no proof to support this story in the real world.

At some point I had to decide what I wanted for myself. Do nothing and keep going with how things were, or try something out of my comfort zone to assess my assumptions. So, I texted her:

"Hey, I've been thinking about you. I saw there's a new movie in the cinema. Would you like to go together this weekend?"

And to my surprise, her response was:

“Yes, I would love to!”

While we waited in the ticket line, she asked, "So, how are you? How have you been?".

And in that moment, I had to make a choice: Do I say the truth? Or should I try to look cool and maybe increase my chances of a friendship?

But friendships are built on truth, not on "coolness." So, I said:

“yeh.. all good. But to be honest, I’ve been feeling quite lonely lately. I miss having friends around.”

And as I braced myself for her pity response, she said:

"Oh, no way! Me too! I've also been feeling alone. I was so happy when you invited me to the movie."

My jaw dropped. She had been lonely too? All those months I'd avoided reaching out because I assumed everyone else had perfect social lives based on a few Instagram photos?

And that day transformed how I make friends as an adult

I love what Alain de Botton says about impostor syndrome, which can also be applied to any negative story we tell about ourselves in comparison to others:

“We feel like impostors not because we are uniquely flawed, but because we fail to imagine how deeply flawed everyone else must necessarily also be beneath a more or less polished surface. We know ourselves from the inside, but others only from the outside.”

Stop waiting for the other person to make the first move

One of the reasons why we don't make as many friends as we want to is because we're all waiting for the other person to make the first move.

After that, I started reaching out more. Turns out, many people I knew were also looking for connections but scared to make the first move—or it didn't even cross their minds, but they were happy to accept the invite.

If you're an introvert like me, I know how hard it is to make this move because small talk used to terrify me, the fear of not knowing what to say and the awkward silence. That's why I wrote this piece on how I moved from hating small talk to embracing it.

Friendship coffee strategy

Today, having lived in a different city in Portugal for 6 years, I can say that many of my friendships began simply because I invited someone I thought was cool for coffee.

I go about living my life, and every time I cross paths with someone whom I like the energy or the vibe, I say: “Hey, you seem like a real cool person. Would you like to grab a coffee? I’d love to learn more about you.”

Coffee is a great way to chat with someone you're not yet familiar with. You can make it as short or as long as you want depending on how you're enjoying the other person's vibe.

If you already know someone who you'd like to get closer to, inviting them for activities like movies, workshops, or sports is a nice way to create shared experiences and memories together — and have something new and in common to talk about.

How to turn people you meet into friends — Here comes the hard part

Meeting people is not the same as making friends. Meeting people is quick, friendships take time. I know people who know lots of people but are constantly complaining that they don't have friends-friends. At some point, this was also me in the past, and looking back now I see two main reasons why friendships were not formed: unrealistic expectations and lack of effort.

There was a time that I expected friendship at first sight. My benchmark was the friendships I had back home (that took me a lifetime to form), and any encounter that didn’t resemble the quality of those connections was dismissed. A coffee or a shared activity won’t turn someone instantly into a ride or die friend. No matter how good the conversation was.

Wanting to become besties with someone without going through the fire together is not realistic. You need to be willing to hang with the same person many times, and sometimes, it won’t feel exciting, or novel, but you’ll get a glimpse further into the inner world of that person, while building trust, familiarity, and consistency. The foundation of strong friendships.

The main reason why adult people struggle with making new friends, is because friendships requires effort, time, and energy. Things that are mostly scarce in adult lives.

If you want to make new friends, you need to be intentional in picking the people who you will invest time on, check-in, and show up again and again.

One of my friends, took me about a year and a half of regular coffee meetups, shared activities, and consistently showing up for each other before I could say we are truly friends.

The advice I received from a monk

Once I went to the Buddhist temple and asked to speak to the monk. I told him how I was feeling lonely and if there was any advice he could give me. Instead of advice, he asked me a question:

"Have you tried helping other people feel less alone?"

Warmly,

Nat

I’d love to know: If you’ve tried to make new friends as an adult, what worked for you? Or what other challenges have you faced? What advice would give to others wanting to find their people?

Leave a comment

I write another newsletter called Diary of a Brand Therapist, where I share the messy stuff behind building a brand and business as yourself.

If you're building something of your own and prefer real experiences over polished business advice, you'll probably love it there too.

My latest piece was “How I’m building my brand with multiple interests”.

“Every other day, I’m sending a link of something I read/heard/watched to a friend. Something relevant to the conversations we had been having.

And since my newsletters are written based on challenges I’m exploring myself and conversations I’m having with friends… why I’m not sharing these links here??”

I have no idea why I never thought of this before. But now, I connected the dots. And here they are: Links I sent to my friends.

Expect them at the end of each month.

But PS: I got so excited about doing this, that I didn’t want to wait until the end of the month, so…

Relationships

• On the importance of choosing your partner well

  What I really wish I knew before Motherhood

  by

Community

• On how to create real community: Showing up and being consistent. (I believe lessons apply to both digital and physical world).

  Stoop Coffee: How a Simple Idea Transformed My Neighbourhood

  By

  ---

  Career

• On the myths of starting over a new career, and why you’re not really starting from zero. “While we’re alive there’s time to live.”

  I just started training for my dream career at 52 (and what nobody tells you about being “too late”)

  by

Communication

• Easy framework to think clearer and express yourself better

  3 rules to express your thoughts so everyone will understand you.

  by Big Think

& If you missed, this is what I wrote in June:

Relationships

• What I learned about having better conversations and connecting with people

  I used to hate small talk until this changed my perspective

  by

  ---

Relationships

• Reflections from hanging with my 89 yo grandma on what really matters when we get older.

  The version of success you don’t learn in your 30s

  by

Communication

• On why building an online presence can make you see yourself more clearly

  Creating a personal brand is an act of self-discovery

  by

I hope you find something helpful!

Warmly,

Nat

Leave a comment

Estimated Reading time: 6 minutes

"I can't find good connections. People are shallow and they bore me. I want deep conversations and friendships. I'm tired of all this chit-chatting."

I wish I could tell you I heard this from someone else, but it was me saying this until a few years ago.

At that time, I used to think that I was a "deep" person. I loved diving into philosophy, psychology, and everything about the meaning of life. Conversations around what to wear, things to buy, recipes to cook, and talks about the weather bored me to death.

Here's the part I'm ashamed to admit but I have to disclose for the purpose of this piece: I used to think that not being interested in chatting about casual everyday life made me better than most people.

It took me a good few years struggling to connect with people in the ways I craved to realize they were never the problem.

Today I will share some lessons I had about connecting with people and making friends, that made me more humble, more open, and more curious.

I didn't know what to talk about with people in my day-to-day

7 years ago I left Brazil with no plan where I'd go. I traveled a bit and ended up in a little village in Portugal.

When I was traveling, I loved to meet new people every day. I felt like everyone was so interesting, they had so much to share, and the conversations were always "deep". They shared their story, what mattered to them, where they were going, their dreams, their ideas, the things they were against, their lessons... there was so much material in every conversation.

But the thing was… 99% of the people I met while traveling I never saw more than once or twice in my life.

Then, I landed in this tiny village. And I discovered a problem I didn't know I had: What do I talk about with the same people I encounter almost every other day?

We're not friends, but we're not unknown to each other. After a few encounters I kind of already know where they came from, what they're up to, and what they're looking forward to. I might even know how they feel about their work, family, or hobbies. So, the question became: What is left to say?

Here's a second confession: I used to hate small talk so much that I would literally hide and change my route on the street if I saw a familiar-but-not-quite-friend coming from a distance.

At some point, I realized I could not continue living like that anymore. After all, I wanted to connect with people and make more friends, so what could I do to change this?

Well, if you know me well enough by now, you know where I find the answers to almost all my problems: books. (links at the end)

The perspective shift that made me enjoy small talk

Think of a close friend or a family member of yours. I bet that there are times you share with each other the most pressing matters of your soul, and there are times you're in silence just enjoying the presence of the other person.

Talking is not required because you're comfortable in each other's presence. You know them, trust them, and just having the person around is enough for you to feel connected.

When you haven't built trust, understanding and connection with someone yet, silence can feel awkward. And that's when chit-chatting comes in.

Small talk is the bridge for connection.

Silence is for close friends what small talk is for people you're still discovering. It’s a way to enjoy each other's presence.

"Ok, great. But I still can't get deep conversations and I don't know what to talk about... how does this help me?" you might be thinking.

I'll tell you what helped me enjoy conversations and feel confident talking with anyone at any time. First, though, I believe that the meaning we give to things forms the foundation of how we relate to them and determines our motivation (or lack thereof) to put effort into them.

So, for me, understanding that small talk is a bridge to connection helped me find the right motivation to implement the next steps I’m going to tell you about.

You want deep conversations, but do you offer depth?

What do you tell people when they ask you: "Hey, how are you doing?"

Let me guess... "Good", "Fine"?

This is how I used to answer that question: "Good, what about you?", and then the other person would say "good too". The silent awkwardness would kick in, I wanted to disappear because I didn't know what to say anymore, and I reaffirmed the belief of how much I hated chit-chatting.

What do you say when people ask you: "Hey, how was your weekend?"

Let me guess... "Good, just chilling", "Oh, nothing special, you know, cleaning, Netflix..."?

That was me too.

The only thing I never realized until I started diving into my research of how to talk to people was that I complained about them not offering me deep answers, but I wasn't doing a better job at it either.

If you want something from others, why not start by offering it yourself?

The first thing you have to know is that people WANT to have interesting and deep conversations as much as you do, but we all need a starting point when we haven't built a solid friendship yet.

BE THE STARTING POINT.

When people ask you the common greeting questions, instead of giving a short answer, tell them a story.

Just share whatever comes to your mind, to give them material to follow up with you.

For example, if you and I crossed paths today and you asked me "hey, how are you doing?"

The past me would say: "I'm good, and you?"

The current me would say: "I'm good, I'm enjoying the quiet day today because yesterday I had such a social day. And I'm not really used to it. I went to the opening of the new collective studio in the morning... have you heard about it? It's so nice, I loved the brands there, I think they align so well with each other, the danger is that if you're a client of one brand, you'll definitely want to buy from the other brands too! So cute."

Do you see what I did? I didn't necessarily talk about myself, and you didn't ask about what I did yesterday, but I shared enough material for you to follow up on what's interesting for you, and eventually we discover a common ground that can lead us into more interesting and personal topics.

In this example, you could follow up from so many different angles:

• About how you also feel tired, or on the opposite, energized, by social events, and how you relate to it.

• About asking which brands were there, and share more about the brands and styles you're into or not.

• About how nice it is/or not nice that the village has been growing in the last years, and how you feel about the development of it, and we can share our perspectives and experiences about it.

The point is, my interactions with people changed entirely when I realized that it was on me, not on them, to lay out the quality of the conversations I wanted to have.

I said that you can share any story that comes to your mind, but what you can also do—and what I do sometimes—is to prepare in advance. If I know I will have a social event to attend, I take a moment to recap in my cell notes what I've been up to in the last week or so, things that caught my attention, or interesting bits I can share in conversations.

Chit chatting helps you to build a sense of familiarity and community

I was also surprised to learn that chit-chatting is one of the main factors that help us to create a sense of belonging.

Esfahani Smith writes in her book, "The Power of Meaning: The True Route to Happiness," that sense of belonging is one of the four pillars to cultivate a sense of happiness in our lives. And she says that belonging is more than having deep, long-term relationships.

What creates a sense of community around us is the frequent, positive, everyday interactions we have with others—like the people who work at the coffee shop you visit regularly, your neighbors, or the old lady at the local market.

I know that one of the things I like the most about living in a small village is the sense of familiarity I have around me. With all the instability we see in the world nowadays, seeing the same people in the same places, and knowing that I'm known by them gives me a certain sense of predictability and safety.

These chit chats we have aren't just filler, they're constantly affirming my presence and the other person who I cross paths with, and even though we might never be close enough to become friends, it reminds us that we matter to others in community.

More to come: How to make friends as an adult

One of the biggest lessons I've learned is that connection takes work. We live in a world where people expect to magically connect with others, like finding love at first sight. I was one of these people. But openness, curiosity, and genuine interest in others demand effort and energy, and it's so worthwhile.

The truth is, it will often take more than a few encounters to turn someone into a friend. That's actually the next part of this story I want to explore with you. The specific strategies that helped me build real friendships as an adult, beyond just improving conversations.

What resonated most with you from today's piece? And would you find it helpful if I shared what I learned about making friends as an adult?

Leave a comment

Also, if you’re curious about the books I read to improve my small talk, here are they: Better Small Talk (my favorite) and How to talk to anyone.

Warmly,

Nat

PS: I just launched a new newsletter called Diary of a Brand Therapist, where I explore the messy, real stuff behind building a personal brand—self-worth, self-doubt, finding your voice, and figuring out who you actually are. It's based on what I see with my clients and my own struggles with putting myself out there.

My first essay there is "Creating a Personal Brand is an Act of Self-Discovery." If today's piece resonated with you, you'll probably love it there too.

Estimated reading time: 6 minutes

The thing is: we all know we’ll get older.

We all know that we will eventually die.

But do we really know know it?

I don’t think so.

I think we know conceptually, but in practice it feels like it’s going to happen somewhere too far away in the future, maybe even in another life.

But lately, I’d say in the last year, the idea that one day maybe not to far from now I will certainly be an elderly person has felt much closer to the reality.

Sometimes, the thought of it makes me uncomfortable, but it has also helped me see life in a more positive light.

It has pushed me to reflect on what makes life meaningful at these later stages of life. I’m starting to understand that it’s not about youth or achievement, but about love and relationships.

What really matters when we get older?

Last Tuesday, I was ironing in my living room while my grandma was sitting on the sofa sewing some of my clothes that needed to be fixed but I was lazy enough to wear them anyway the way they were.

We spent most of the time in silence.

At times, she made sporadic comments bragging about how her sewing was perfect, and I’d agreed with her in response, making sure she knew how awesome she is.

Even though we didn’t speak much, from time to time I would look at her and my heart would fill with joy for this moment.

“I’m so grateful for this” I thought a few times.

My mom was in the next room trying some of my clothes I didn’t wear anymore, choosing which ones she wanted to take back with her to Brazil.

My grandma is 89 years old, but don’t let yourself be fooled by her age - she is a vivid, sharp woman, and has impeccable skin.

She is visiting me in Portugal for the first time since I moved here 7 years ago. My grandpa died just a year and a half ago, at the age of 97, and they had been together in total for 70 years.

It’s needless to say how hard it has been for her this time without him, but I also realized how having her family around and grandchildren to visit in different cities, even if once or twice a year, is what gives her meaning and joy at this stage of her life.

I call her every Sunday, and we speak for about 20min. She spends the entire week telling others about the call we had, and looking forward to the next Sunday call, even though we mostly talk about the same things every time.

The thing is, it’s not about what we discuss, it’s about feeling the other person present, connected, and knowing that you’re remembered. Being loved.

I think everything we do in life is about feeling loved - even the things we think there’s nothing to do with it.

“I knew you’d call, you always call”, she says every time when she picks up the phone.

Having her over for these last weeks, has made me think: How do I want to see myself when I’m 90?

Family Is Hard — and Worth It

What I’ve been recognizing for now is that at the end of the day what really fills my heart with joy is the connection I form with people, and there’s no connection like the one’s we form with our family.

In full transparency, I’m not here to romanticize the ideal of family, and say how perfect and loving, and rainbows and unicorns, families are.

Family is really hard.

My grandma is a woman of strong personality, and if I had to be with her everyday of the year I probably would complain about her often.

But since I’m far away, when I’m close to her I don’t care at all about the things that would annoy me, and I just focus on her qualities and how grateful I am for spending time with her.

Also, if you have been reading along since the beginning of this newsletter, you’d known how much I had to work through a collection of traumas with small “t”s I carried from childhood.

Which means that when I was younger my relationship with my mom was very conflicting and I spent probably around a total of 10 years in therapy to make sense of it all.

I rode the entire rollercoaster of emotions along the years in relation to my parents. And only in the last years, after I started taking real responsibility for myself, I was able to heal more and more, accept them as who they are, and be grateful for everything they offered me - even if in imperfect ways.

To have love and connection, we need to take responsibility for ourselves.

Watching my grandma light up when I call her every Sunday made me realize that love isn't just showing up for others, it’s also showing up for ourselves, so we can relate with openness instead of defense.

I think that part of developing a good relationship within our families is our ability to take responsibility for ourselves, which implies in creating boundaries when needed.

One of the things I understand now that created so much conflict in the relationship I had with my mom, is because even though I was an adult, I was still expecting her to show up for me in ways she couldn’t.

It was only when I started showing up for myself as I needed, that I could release the expectations I had on her, and be accepting of how she is, with her gifts and limitations.

It also means that I became more protective of myself, and I had to communicate limits in our relationship when something was triggering for me.

I’ve noticing that the more I show up for myself, the better I can relate with others from a place of compassion instead of judgement like I used to do in the past.

I feel lucky that I’m at this place that I can embrace my family with so much love and compassion for their imperfections, knowing that I’m also imperfect.

And what helped to do so was developing my abilities to communicate boundaries and be firm with them (not easy, very necessary, and a work of a lifetime for a recovering people pleaser like me).

Taking responsibility for myself also means recognizing that I’m an adult, and that they owe me nothing. That I’m deeply grateful for all I received, especially my life, and all the love they gave me in all the way they could and knew how to.

And that whatever I get from them now, I receive it as a gift. Their time, their love, their support. I recognize that I’m only able to live the life I love right now because I always knew that no matter what happened I would always have my family to support me.

At this moment of my life, I think that knowing who I am, while having an imperfect family that supports and loves me, is the best thing in the world.

Research shows that love is what keep us alive

I remember when I was reading Man search for Meaning by Viktor Franklin, who was an Austrian psychiatrist and holocaust survivor. He described the experience as being a living hell — one which many people chose to end their own lives so they could free themselves from all sorts of psychological and physical pain.

In very simplified terms, he points out in the book that, that the difference between people who endured such a living hell and unthinkable pain, and the people who didn’t, was that the first group was moved by a sense of meaning and purpose in life.

For many of them, this came from their families and loved ones, from whom they were separated when taken away. Because of those connections, they felt that they had to survive all of that so that they could eventually reunite with them, and be there for them.

From other books and stories, I noticed this to be the same motivation for people who endured hell and survived wars moved by their families and lovers.

And, as always, I’m curious to know if there’s foundation to my observations, so I did a quick research and found that..

a Harvard study, the longest-running one from 1938, found that elderly people who have strong social connections, especially with family, tend to live longer and have better health outcomes. And that close relationships, more than money, fame, or work success, is what keep people happy and healthy as they age.

Not only that, an analysis of 148 studies made by Holt-Lunstad et al. (2010) on the topic concluded that strong social relationships increase the likelihood of survival by 50%!!

What success looks like for me when I’m older

Reflecting on all this, I’ve come to see how unique and irreplaceable the love of a family can be. It’s knowing there are people in the world who love you so deeply, they would step into your shoes without hesitation.

For my parents and grandma, the most joyful moment of their week is when I call to speak for 20 minutes, often just to talk about the same things over and over again.

When you’re young, everything feels urgent — so many goals to chase, things to build, lives to live. But watching my grandma this past year, I’ve realized that when I’m at her age, the only thing that will truly matter is the people still sitting beside me. The people who know me, who remember me, and who still call.

And I don’t want to wait until I’m old to appreciate that.

Someday, if I’m lucky enough to reach 90, I hope there’s someone I love waiting to hear my voice—and that I’ll get to say:

“I knew you’d call, you always do.”

These are my reflections for the week. Curious to know if you can relate :)

With Love,

Nat

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Sometimes I also dream of working in a coffee shop, but unfortunately it doesn’t pay the bills.

My friend is in her 40s and has lived all over the world, from the U.S. to Japan, working as an international school director shaping educational programs. Now, settled in Portugal, she works remotely coaching other educators in her field.

Lately, I’ve noticed how many of my conversations keep coming back to the topic of "work”. Whether it’s the overwhelming amount of it, the lack of it, or the need to find a new path altogether.

Something I’ve been reflecting on is the pressure our generation created around the idea that work must be purposeful, impactful, and world-changing. We were told that work is not just what you do, it’s who you are.

It's a beautiful idea, but in practice I wonder how much pressure it adds to the choices we make and the paths we follow. What happens when those paths no longer feel right? Yet we often resist changing direction because we've built our entire identity around what our "purpose" is supposed to be.

But if we spend most of our lives working, shouldn’t work feel meaningful?

I do believe that meaning is essential. In work, in relationships, in hobbies. It’s a crucial part of living a coherent and fulfilling life that feels aligned with who we are.

But meaning and purpose are not the same thing.

My critique is about the idea that we need to find one single purpose in life, and that this purpose must be fulfilled through work. The promise is that once we find it, we will live “happily ever after”.

When work becomes the center of our lives, not just in hours spent but as the compass that guides our sense of self, it can carry an overwhelming existential weight. One that, sooner or later, can break out not only as a professional crisis, but as an identity one.

The millennial generation grew up internalizing the belief that we are what we do. But when what we do no longer makes sense to us, or no longer fits within a changing world, then who are we?

Research shows millennials are likely to have 3 to 5 career shifts in their lifetime, while Generation Z is expected to have 4 to 6.

We’re not only living longer but the world is changing faster - and so are we.

The pressure to find purpose at work is heavy and often misguided

The concept of finding purpose at work gained mainstream popularity in the 1990s when advancing technology opened new possibilities, coupled with a culture of individualism that promised self-actualization and fulfillment through professional achievement.

What didn’t come with the message was that even if you do find purpose in your work, it might only serve you for a period of time in your life. Purpose can also be temporary.

If you’re doing life right, you’re growing, evolving, and becoming different versions of yourself through new experiences, new insights, and shifting contexts. The idea of a fixed, static purpose doesn’t fit into that.

So it’s only natural that as we evolve (hopefully into more mature versions of ourselves), what once felt meaningful might no longer feel that way.

Purpose can become an identity trap & the AI revolution

When we define ourselves by a ‘single purpose,’ we can end up feeling stuck. We stay in careers or businesses that no longer fit, simply because they once did. I’ve seen it happen again and again, and I’ve lived it too.

When I was doing brand strategy for companies, I believed I had found my purpose. Yet over time, work that once energized me began to feel hollow. It wasn’t the what that felt off, it was the why. The impact no longer felt rewarding to the person I was becoming.

Still, I stayed, because I had built my entire identity around that work.

It took me two years to shift my focus to what truly mattered: people. On the surface, it seemed like a small change, after all, I was still doing brand strategy. But I had moved from building brands for companies to building brands for individuals. And because I’d tied my sense of self so tightly to the old work, even considering a different angle felt difficult at first.

In this era of the AI revolution, when no one knows what the future will look like, tying your identity to what you do is like building sandcastles. When the tide rises, it will inevitably wash them away.

One of the greatest freedoms I’ve gained in recent years is detaching who I am from what I do, understanding that I’m a valuable person not because of my work, but in spite of it.

We don’t talk enough about the emotional toll this takes. The shame of not having found a ‘purpose,’ the guilt of wanting to change direction, the paralysis of waiting for clarity before starting.

I’ve seen people spend years—even decades—waiting to find a purpose before taking action. But more often than not, that clarity never comes.

Chasing purpose can be like chasing the end of a rainbow, you think there’s a pot of gold, but you end up lost and empty.

I know it sounds cliché, but meaning comes from the journey, exploration, discovery, and contribution. Not from a fixed sense of identity.

The future of work is experimental

I no longer believe in finding one single purpose.

I believe in living on purpose: staying connected to what feels alive in you now, following your curiosity, and allowing your outer world to evolve alongside your inner world.

The future of work isn’t about having it all figured out. It’s about paying attention, experimenting, and letting yourself change without shame.

It’s definitely not about finding a singular, fixed purpose but embracing curiosity and constant evolution. As the world changes, so do we, and experimentation allows us to align our work with who we are becoming.

By living on purpose instead of searching for one, we can adapt to uncertainty with intention and openness.

Maybe the future of work is not about creating for constant impact or grand transformations, but about being fully present in whatever you're doing now.

Even if it’s as simple as making a good cup of coffee, smiling at someone, and going home.

Not everything has to be about impact and change, it can also be about simplicity and presence.

What if it’s not about discovering your one true calling, but about learning to keep answering the next one?

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I'd love to hear your thoughts and experiences with on this.

With Love,

Nat

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P.S. Beyond these reflections, I help individuals turn their story and lived experience into a brand and business that feels true to who they are, if you’re curious, you can explore more here.

Have you ever noticed how easy it is to see solutions to other people's problems, while our own challenges seem far more challenging to figure out?

I believe that most often than not, we stand on our own way to get the things we want.

Last year, I found myself stuck: I wanted to connect with more people, make more friends, create new things, and communicate more on social media. However, for reasons I couldn't pinpoint, I couldn’t get myself to do it.

Until one day when I decided to write down what was holding me back, and the answer was simple: the beliefs I was holding about myself.

Then one day, I started noticing these things I kept repeating to others in conversations and to myself to justify certain situations in my life. Things like:

• “I’m not a doer.”

• “I’m not good at socializing and making friends.”

• “People are paying close attention to me and judging me by what I say or do.”

But in the moment that I really became of aware of it (when I wrote it down), I had a weird feeling. Deep down I suspected that they weren't totally true. So, I decided to search for evidences.

And what I discovered was that, for each evidence I could point that those were true beliefs, I had 10 others evidences that showed me that they weren’t. For example:

• How come I’m not a doer, if I have been running my own practice for over 7 years?

• How come I’m not good at making friends, if I moved to a new country and created new relationships from scratch to a point I do feel I have a community around me?

• How come I think people are judging me, if I never received a critique or hate for anything I put out there? Quite the opposite really?

I felt conflicted. After all, are these things I was thinking about myself, true or not?

Limiting beliefs

When I reflect on this, I think the most important question to look at is:

If I had more evidence that these beliefs were not true than evidence that they were, why does my mind routinely accept them as valid?

The answer is simple: the weight of emotions.

Beliefs are not just thoughts, they are thoughts attached to strong emotions that make our sense of identity.

If we find ourselves in one situation that cause us a strong emotion, this bad situation will overweight 100 good ones that didn't have as a strong impact.

When I look back, I know exactly which single situation that caused me a strong negative emotion that led me to repeat these beliefs in my mind over years, even though they are not really true to who I am on a daily basis.

Real evidences or interpretation of reality?

Committed to reshape these beliefs, I decided to dive and study more deeply about how what we think about ourselves can impact the results we get in life.

I learned that the reason why many of us get stuck in negative beliefs is because we see them as inherent to us, in other words, that they are the reality of how things are (or how we are), independent of our perception.

But the real truth that neuroscience reveals is that much of the reality we experience depends on the way we perceive things (and I will prove it to you below).

Vanessa Van Edwards, a specialist on the science of people, explains that people who believe they are disliked often interpret neutral facial expressions as angry ones, creating a negative cycle. When we think others dislike us, we tend to shut down and become less approachable.

She shares a study done by Dr. Van Sloan that investigated "What makes popular kids popular?" They studied thousands of high school students across many schools, looking for patterns. They discovered that what made popular kids popular was not that they were more athletic, attractive, funnier, or smarter. They found out that the most popular kids had the longest list of people whom they liked.

Think about it, if you like more people, you’re naturally more open to others, nicer to others, leading you to create multiple moments of small connections throughout your day - which in turn makes you more likeable.

The way we feel about ourselves dictates how we expect others to act towards us.

Verifying our evidences

Beliefs are sustained by evidence. The problem is that we are biased to interpret situations based on how we feel about ourselves (just like interpreting resting neutral faces as angry faces, as I mentioned before).

This is what psychologists call confirmation bias, the tendency of people to find ways to confirm their own beliefs. Self-verification is when we use this bias to confirm what we believe about ourselves.

Like when we focus on that one piece of evidence that confirms what we believe about ourselves, and ignore the other 99 pieces of evidence that show us that the opposite is actually true.

It’s the unseen biased perceptions that leads us to repeat old patterns that we keep complaining about in our lives. When we start to question our biases we start opening up the possibility of change.

The more we recognise our bias, the more we begin to open up to and search out to a more objective perspective.

Self-verification done in the right way

When I decided to write down my limiting beliefs and study them more closely, it became the turning point where I began gathering the right evidence and taking action to change them.

I did an exercise of writing down evidence in my own life that disproved those beliefs and created a consistent practice to generate more evidence to override those specific beliefs.

It looked like this:

• “I’m not good at socializing and making friends.”

  • Evidence: Almost all new friends I did living abroad started because I INVITED THEM FOR A COFFEE after crossing with them somewhere and thinking that they looked like a cool person.

  • Practice: I started using the Breakfast app, an app that connect modern creatives over breakfast (or coffee) - it’s not dating not networking - just coffee. And I committed to go for a coffee with a new person at least 2x a month.

• “I’m not a doer.”

  • Evidence: I created products, started businesses, engaged in multiple creative projects, and said yes to opportunities that I didn’t feel completely ready for it but very eager to learn and grow in the process.

  • Practice: At the time, the practice was to create and launch a day retreat project with a friend in a topic I was not too familiar with yet. (Today, It turned this practice into creating a max window of 48h between having an idea and starting executing it.)

• “People are paying close attention to me and judging me by what I say or do.”

  • Evidence: In this case the lack of evidence was the evidence. People are too busy thinking what people think of them to think something about me.

  • Practice: Join a public speaking club, and publishing at least once a week a piece on social media - from a creative place instead of based on what I thought others would like.

It's true that practice helps us grow, and practice with direction (new knowledge) helps us develop with more confidence and faster.

For example, when I was going to meet new strangers through the breakfast app, beforehand I'd prepare questions I could ask based on their profile, or study on YouTube ways I could have better small talk and move faster into meaningful conversations.

How to change your self-limiting beliefs

1. Start with writing down the beliefs you have about yourself, just like I showed you.

2. Then try to identify the emotion around that belief.

3. Look for real evidences in your life around that belief and note them down.

4. Commit to a practice to create new evidences around that belief.

I'm still working on some personal limiting beliefs, and I think this is a work of a lifetime as we are constantly becoming aware of new parts of ourselves, but I've been reflecting on how powerful and amazing it is to know that these are not rigid facts but more of perceptions that we can shape in the direction that serves us best.

Our beliefs guide the way we approach life and relationships. When we change how we see ourselves, we change the results we get in life.

With Love,

Nat

I’d love to hear your thoughts and experiences with on this. Have you ever notice self-limiting beliefs? What have you done about it?

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