Announcements and Upcoming Events

Hey everyone, welcome back!

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My friend Eric and I hosted our first ever webinar last Friday! We had 300 sign ups!

We want to create a community for high achievers navigating the messy middle. Your input here will help us design a community that gives you the most value. Please fill out the survey here.

I’m hosting 3 more events this month!

  • ONLINE: Fireside chat with Brendan Burns on 2/18 @ 4pm

  • Brendan is a serial entrepreneur and Professor of Entrepreneurship at Columbia Business School

  • NYC IN-PERSON: Fireside chat with Andrew Yeung on 2/27 @ 5pm

  • Andrew has built +80k followers on LinkedIn and bootstrapped his business to +$1M ARR in 1 year, all powered by world-class community building

  • NYC IN-PERSON: Fireside chat with Hannah Zhang on 2/28 @ 10am

  • Hannah has a crazy non-linear career. She was an investment banker, the 1st marketing hire at a Series A startup and grew her personal brand to +100k in 6 months

What happened?

March 2023 - Halfway through my 3 months of 4ams

9 months into banking, I burned out.

It was winter in NYC and I was getting home at 4am every day. That went on for 3 months in a row.

During that time, I started crying every day, having panic and anxiety attacks…

I was deeply miserable, which was unlike me. I’m a pretty smiley and calm person.

Most mornings you can catch me listening and singing along to Gilsons.

I knew there was something wrong.

And since then, I know I wanted to leave banking.

I had saved enough money to take a gap year, go travel or pivot to another job.

On paper, I had freedom and could choose any path.

So I asked myself the obvious question:

  • What do I want to do?

  • What are my passions?

  • What gives me energy?

I had no idea.

I felt like I didn’t know who I was.

The biggest identity crisis of my life started.

The obvious next step

So I started researching.

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

For more than 1 year, I was endless researching my next move.

I was taking action to collect information, but I wasn’t moving forward.

I still felt like I had no idea who I was or what I wanted to do.

The list of career options to explore kept growing, not shrinking.

I was stuck.

The problem

I was treating figuring out who I was and what to do next 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 what high achievers do.

We optimize, we analyze different paths, we collect information until we find the optimal path.

It had always worked before.

It got me to #118 in the world in tennis and to Wall Street.

So why wasn't it working now?

The real fear

After 2 years of endless research and still stuck at banking, here's what I realized:

Identity gap is not a career problem.

It’s a self-worth problem.

My entire life, I optimized for optionality.

Tennis rankings → D1 scholarships → Wall Street → Financial freedom to take risks

There was always something concrete to optimize for and a clear next goal.

And these paths happened to be impressive, so my identity got built on that.

After 16 years of tennis and banking, I finally had the option to choose something based on what I wanted, not what would give me more optionality or look impressive.

That terrified me.

Because underneath all my research was one constant fear:

Without an impressive job, I will be found out as ordinary.

And being ordinary felt like failure.

The first step forward

To move forward, I had to let go of that fear.

But here’s the problem:

When I let go of the need to be impressive, I was left with nothing.

No identity and no direction.

Just 1 question:

Who am I underneath all of this?

From talking to dozens of high achievers navigating the messy middle, I realized that most of us share the same fears.

Most common fears are:

  • Lose status

  • Lose financial safety

  • Failure

  • Being found out as ordinary

Which one is yours?

How I rebuilt my sense of self

What actually helped wasn’t figuring out the next career I wanted to build.

It was looking inwards and rebuilding a sense of self.

I did that in 3 layers.

1) Identity

  • Who was I as a kid? What did I like?

  • What are my intrinsic characteristics? (caring, kind, curious)

  • What behavioral patterns do I have? (therapy + journaling)

  • What is the impact I want to have in the world?

2) Values and energy

  • What are my top 5 values?

  • When am I in flow?

  • What gives me energy?

  • What makes me curious?

3) Redefined sucess:

  • Redefined what a good day means: a day lived by my values

  • Learned to feel valued without my job title

When I rebuilt my sense of self, choosing the next experiment became easier.

Not because I had it all figured out (I still don’t).

But because I finally learned to listen to myself and understood what kind of life would actually make me happy.

How to do it yourself:

  1. Open your favorite note-taking app (I use apple notes) and create 3 sections: Identity, Values & Energy, Redefined Success

  2. Write down the questions above

  3. Set aside 30 minutes a week minimum to reflect on those questions. No phone and no distractions.

  4. Start with Identity and move through the layers as answers emerge

  5. Throughout the week, whenever you notice something, jot it down in whichever section it belongs to

Don't get caught up in following a specific order.

What matters is that you start thinking about these questions and answer them as they come to you.

The good time journal

Good Time Journal

Here’s how you do the Good Time Journal exercise:

For 2 weeks, track your activities daily and how you felt during them.

Ask yourself three questions for each activity:

Was I engaged? Was I in flow? Did it energize me?

Fill the answers in the journal.

Examples:

You did a pitch presentation in the morning. Were you engaged? In flow? Did it energize you?

You had a coffee chat with someone from VC in the afternoon. Were you engaged? In flow? Did it energize you?

What to look for:

Notice which conversations you're attracted to, which activities and people energize you.

Over time, patterns will emerge.

You'll have a much better sense of what gives you energy and what puts you in flow.

And that clarity is key in choosing your next step.

Designing Your Life is a book I wish I had read earlier on my journey. I recommend it to everyone navigating the messy middle.

Q&A

Anonymous:

How do you trust in the leap of faith and that you will find something you are passionate about when you work through the burnout?

My answer:

The worst thing that could happen to me after spending 12 months of savings? I'd have to find another job. Staying stuck at a job I hate vs the chance to design a life I love felt like a no-brainer.

I started from a blank page. No passions and no idea what I even liked. It was hard to believe I'd uncover anything.

Before looking for my passion, I had to let myself recover from burnout by giving myself proper time off. Once I recovered, my curiosity started to come back. That curiosity became my main driver and I followed it without forcing answers. From there, things naturally emerged. A noticed a love for writing, deep conversations and being surrounded by ambitious people IRL.

What I believe now: we all have passions/likes waiting to be uncovered, but they need space to surface. You can't rush it. You have to recover first, then let curiosity lead. Trust that if you give yourself enough space, something will emerge.

Ask me anything anonymously:

As always, thank you for reading.

Vitoria

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