#100: What 100 Newsletters Taught Me

From Imposter Syndrome to Identity

👋 Hey, Leo here! Welcome to The Antifragile Leader. Each week, I explain the concepts needed to lead through uncertainty. Subscribe to get every issue in your inbox.

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I started this newsletter a bit over 2 years ago with a confession:

“Starting out new things is an experience full of anxiety and feelings of imposter syndrome. Re-starting is even worse.”

Tech Leadership Unplugged #1: A New Beginning

That was 100 weeks ago.

Back then, I didn’t know if anyone would read it. I wasn’t even sure I’d keep going.
I had no grand plan—just a quiet promise to myself to write, share, and figure it out along the way.

And now, here we are. Issue #100.

From April 7, 2023, until today, I have written one post every week.

Without missing any.

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The Hard Parts

There were plenty of moments when I didn’t want to write.
Weeks when life was too much, or work was overwhelming.
Days when I stared at a blank screen and thought, “Does this even matter?”

I don’t want to complain, but especially these last few months have been crazy.

• It’s the final stretch for my MBA (I started the last official course yesterday);

• Zeno came into our life 3 months ago;

• We had to do a lot more work than we expected to renovate the new apartment (I hope we can move in next week)

all this while leading the local tax technology team at Deloitte, getting some workouts in every week, and keeping my sanity in the process.

It’s not easy. But most things in life that bring you satisfaction aren’t.

I’ve written through exhaustion, imposter syndrome, self-doubt, and, at times, complete lack of inspiration.
There were Sundays when I told myself, “I’ll skip just this ”once”—and somehow, I didn’t.

And if I’m honest, there were moments I almost gave up.
Not dramatically, not all at once. Just… slowly.

Silently.
The kind of giving up that comes disguised as “I’ll come back to it later.”

But I didn’t.
Maybe it was the quiet accountability of having promised something to myself.
Maybe it was the idea that even if just one person found it useful, it was worth it.
Maybe I needed it too.

This newsletter became a mirror. A habit.
A tiny act of resistance against the chaos of everything else.

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The Gifts I Didn’t Expect

When I started, I thought I was writing for others.
To share insights, lessons, and maybe offer a helpful perspective.
But I didn’t expect how much it would give back to me.

Writing every week helps me think more clearly.
It forces me to slow down and reflect on what I actually believe—about leadership, about change, about people.

Writing every week sharpened how I communicate, but also how I listen—to my team, to my inner voice, and to the world around me.
I didn’t expect that in trying to teach, I’d learn so much more.
I didn’t expect this to become part of my identity.

This isn’t just a newsletter anymore.
It’s a practice.
A place to think in public.
To connect with people who are also trying to lead with courage and curiosity in uncertain times.
It’s one of the few things in my life that truly feels mine.

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A Few Themes That Kept Coming Back

Across these 100 weeks, I’ve changed the newsletter’s focus and names several times.

Initially, it was the “tech leadership unplugged,” then I changed it to “level up ladder,” then it was “tech leadership playbook,” and now it is “the antifragile leader.”

And I’m sure I’ll change it in the future again, because we change, and our interests change.

But among all these names, some ideas kept resurfacing—not because I planned it, but because they matter deeply to me:

• Leadership is about becoming, not knowing.

• Chaos isn’t something to avoid—it’s where growth lives.

• The strongest leaders aren’t the ones who never fall—they’re the ones who learn from their failure and rise better.

• Antifragility isn’t just a concept—it’s a daily choice.

• Writing is thinking. Sharing is connection. Consistency is transformation.

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Thank You

If you’ve read even one edition, thank you.
If you’ve ever hit reply, shared an issue, or sent a kind word—you’ve helped keep this going more than you know.

You’ve made this journey feel less like shouting into the void and more like a real conversation.
You’ve helped me believe that showing up—even imperfectly—matters.

So thank you for being part of this.

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One Final Thought

If I’ve learned anything in these 100 weeks, it’s this:

You don’t find your voice. You build it.
Week by week.
Word by word.
Even when you’re not sure anyone’s listening.

And I don’t know what’s next.

I’m sure that writing is a craft that you never stop developing.

And that we learn something new every day, until the day we die.

I know I should be making more efforts to market this newsletter.

Because I want it to reach more and more people who might find it helpful.

Who might need it.

I don’t know what the future holds for me, let alone this newsletter.

But I’ll keep showing up here, every week.
Because this is where it started. And it still matters.

Thanks for being here.

It means the world to me.
–- Leo

Here are the 5 editions I think would be the most useful (some of them are quite personal, so you can find a lot about me by reading them).

#28: How often do you step outside your comfort zone?

#49: How to keep up with a full-time job and other interests

#68: AMOR FATI

#65: The "Sunk costs" of your career

#89: A brutally honest review of 2024

Recommendations:

1. I’m in a phase in which I appreciate older things more than new things. It might be the age or nostalgia; I don’t know. What I know is that I am currently rewatching movies from the 90s and early 2000s. Those movies that got me to love cinema when I would sit all weekend watching HBO. And this week I rewatched a ‘92 classic, “A Few Good Men,” starring Tom Cruise, Demi Moore, and Jack Nicholson. If you haven’t watched it yet, do that; it’s got some formidable acting.

2. As some of you know, I’m obsessed with productivity and high-performance. And it all starts with an effective morning routine. If you want to start your day right, you can begin with a simple routine, explained by Tim Ferris below, on which you can expand later.

3. The Proust Questionnaire. Originally a parlor game, this set of questions can make you think for a minute and if you answer the questions you could find some new things about yourself and about the people around you.

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