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I'm building something I wish existed when I was between identities. A community for high achievers stuck in the messy middle. You've outgrown what got you here, but haven't landed on what's next.

Before I build it, I want to get it right. This survey shapes what goes into it (and who gets early access). Please fill the survey out here.

I’m hosting 2 more events this month!

This Wednesday (2/18/26), I hosted a fireside chat with Brendan Burns. He is a serial entrepreneur, professor of entrepreneurship at Columbia Business School and someone whose students have gone on to build and sell companies for hundreds of millions of dollars.

He said something that I haven't stopped thinking about.

From a young age we are trained to follow rules.

You get good grades and everyone tells you you're on the right track. You get into a good college and it confirms it. You land the prestigious job and now you're really winning. Each step feeds you more dopamine.

The system rewards you for performing at a high level within its rules. So you keep doing it. You optimize, you conform and you keep collecting gold stars.

And it works.

This is what got me to #118 in tennis and Wall Street. It probably got you to wherever you are right now.

But here's the problem: you get so trained to play by the rules that you forget you can make your own.

Brendan teaches at Columbia Business School. He told me that second-year MBA students who don't have an offer from McKinsey or Goldman by February think they've failed.

Brendan’s word for that? Bullshit.

But I get it. I was this person for most of my life. I spent my entire life inside systems that told me what success looked like. First it was tennis rankings, then GPA, then a fat bonus in banking.

When I left Citi, those rules vanished.

And I froze.

When the rules disappear, high achievers don't sit still. We do what we've always done: research, analyze and optimize.

I did +100 coffee chats, went to IRL events, took personality tests, did therapy, etc.

I was taking action, but I wasn't moving forward. The more I searched, the more the list of options kept growing, not shrinking.

I was treating figuring my identity crisis like a research project. Like if I just gathered enough data points, analyzed enough career options and did enough coffee chats, the answer was going to appear.

This is the default mode for people like us.

We think the way out is through more information, more analysis and more thinking.

It's not.

Someone asked Brendan how to get past analysis paralysis.

His answer was simple: stop analyzing and start moving.

The hardest thing as an entrepreneur is to learn how to move forward in the face of uncertainty.

Brendan says: “when in doubt, do something.”

Even if it's just getting up and walking around the block. Even if you get it wrong the first time. Movement creates momentum.

And that momentum has a way of carrying you forward.

That's it. DO ANYTHING!

I spent a LOT of time stuck in analysis paralysis. I wanted to figure it all out in my head first. Plan the perfect exit, build the perfect business plan, then execute.

But that perfect plan never came. It never does.

You can't think your way into what's next. The only way through is action. Even when you don't know where it's taking you (and you won’t know).

The research phase felt productive, but it wasn't. It was fear dressed up as due diligence.

My progress started when I stopped asking "what should I do?" and started actually doing things. I started an Instagram about personal development, I wrote, posted on LinkedIn, went to IRL events. I actually tried things.

Most of the things I did went nowhere. But a few of those messy experiments are the reason you're reading this right now.

And why my life looks nothing like it did 1 year ago.

At the end of the fireside chat, I asked Brendan: if you could give one piece of advice to everyone here, what would it be?

He told a story about his mother.

She survived polio as a kid, aplastic anemia at 40 (which was basically a death sentence at the time) and COVID in her late 70s. She became one of the longest-living people ever diagnosed with her condition.

Brendan told us that his mom climbed stairs until a few weeks before she died of pancreatic cancer in her late 70s.

His mother-in-law was the opposite. Sharp mind, played piano 2 hours a day until the end, but she didn't have a physical practice. She spent the last 3 years of her life unable to walk.

Same generation, but two completely different outcomes.

His advice: if you have a choice, always take the stairs.

It's a metaphor for everything.

As we make more money, we sign up for more comfort. The Uber instead of the subway, the dinner out instead of cooking, the safe job instead of the scary leap.

Comfort compounds. And before you know it, you've built a life optimized for ease, not growth.

The messy middle is a HUGE staircase.

There is no elevator, no shortcut and no hack. You just have to keep climbing.

Brendan had a professor who, on the first day of class, told the room: if you stay through the end of the semester and apply yourself, I will teach you the key to happiness in life.

Here's the system he taught them:

Step 1: Write down the areas that matter most in your life. Not your career goals, your life. Things like: personal relationships, romantic partnership, health, spirituality, professional growth, intellectual curiosity, being a good parent and charitable giving. Whatever is true for you.

Step 2: Rank them. Long-term, there's only one #1. Short-term, there's only one #1. They don't have to be the same.

Step 3: For each area, define one or two simple habits you can practice on a weekly basis. If health is a priority, maybe it's working out 3x a week. If it's relationships, maybe it's 1 meaningful conversation a week. Nothing complicated.

Step 4: Every 90 days, review. Look back at how you actually spent your time, adjust the rankings and beahviors if needed.

Step 5: Redo it.

That's the whole system.

Brendan explains that what makes it powerful is the grace built into it. You're not trying to be perfect at everything at once. You're acknowledging that right now, this is my primary focus. By doing that, you give yourself permission to let other areas be "good enough" for this quarter.

Brendan said he also uses it to make hard decisions in the moment. When you have conflicting interests and imperfect information, the rankings act like a compass. You already know what matters most, you just have to listen to it.

And if you have a partner, share it with them. Not necessarily everything, but enough to say: here's what I'm trying to do, here's what we're trying to do. Let's figure it out together and give each other real grace that we're not going to be perfect.

This reminded me of Henrik Werdelin's 8+1 framework. Henrik is the co-founder of Bark, a business with +650k subscribers and hundreds of happy employees.

The overlap is clear. Both frameworks are built on the same idea: if you don't deliberately track what matters across every area of your life, the urgent will always eat the important.

I asked Brendan how he identifies ideas worth pursuing.

He said: find a problem that really bothers you. Something you care about deeply and are intrinsically motivated to work on.

That's the starting point: a problem you can't stop thinking about.

One of his students at Columbia, Jon Stein, asked a simple question: how come there's no good financial advisor for people my age? That question became Betterment, worth +$1bn today.

Ryan Peterson, founder of Flexport, took a different path. He followed an interest in import-export that seemed arcane at the time, but he went deeper and deeper on it. Years later, Flexport is worth billions.

Brendan's path was different again. He had zero background in art, but he got curious about living artists. How they work, what holds them back and why the industry wasn't serving them. He spent years going deeper and deeper into that one problem. Eventually, that curiosity turned into his latest company.

The pattern across all three: none of them sat down and picked the optimal idea. They followed something they genuinely cared about, went deeper than anyone else and stayed in it long enough for the opportunity to reveal itself.

There's no shortcut for that either.

You were trained to follow rules.

That training served you well and it got you to this point.

But the truth is: the skills that got you here won't take you to your next level.

There is as much unlearning as learning to do while you navigate the messy middle.

The old rules are gone and the instinct will be to analyze your way forward. To research, plan and wait for certainty.

But certainty isn't coming.

The only way through is to move.

And when you move, take the stairs.

Choose the thing that's a little bit harder, a little more uncomfortable and a little scarier.

Anonymous:

Did you consider internal mobility and one sick leave before leaving and why did you not go with this? Was a clean break better for your recovery and what would be your advice for those in a similar situation who are considering options before leaving a ‘good company’?

My answer:

On internal mobility: I considered it, but I was only open to moving to the VC team and they didn’t have spots. I wasn't willing to do corporate banking, sales and trading or any other role that wasn't at least aligned with where I thought I was heading. To me, that felt like trading one misalignment for another (aka a waste of time).

On leave of absence: I took a 3-month leave of absence in 2025 during my 3rd year at Citi and it was the best decision I made. I wish I had done it sooner.

On the clean break: Here's what I didn't expect: even during my leave, I was still anxious and depressed. I was researching, trying to figure out what was next and still in problem-solving mode. I never fully recovered until I did a 7-day ayahuasca retreat in the Peruvian amazon with zero access to my phone, the internet or the outside world. You don't need to be that extreme, but I do believe that real burnout requires a full stop. Not time off to figure things out on the side. A full stop.

My advice: If you are truly burned out, take a leave of absence and actually rest without trying to figure out what's next. Go travel the world for 3 months or do something you always wanted to do. The only rule is: follow your curiosities and let yourself relax.

My one regret about my leave is that I wish I had used those 3 months to travel the world wihtout trying to solve my life.

Ask me anything anonymously:

As always, thank you for reading.

Vitoria