Hi all,
A personal letter coming at you today….
As some of you know, I have been on the journey of writing book #2 and, I’ve got to say, it’s so much fucking harder than book #1.
(and not just because I'm 7 months pregnant and sleep like a rotisserie chicken all night)
It got me really thinking.
I once saw a founder who exited a huge company talk about how they are paralyzed to work on anything now. An excerpt from his LinkedIn post below...
Once you experience success once (in my case it was hitting the USA Today Best Seller list for two weeks in a row)....I now have a case of....
dun dun dunnnnnnnn
Higher expectations.
Why does success invoke fear?
Wouldn’t we think that a proven track record of success would instill confidence?
The answer, I think, is this:
Success changes the baseline.
There’s a psychology concept called loss aversion.
It basically says that once we have something, we become far more motivated to avoid losing it than we are to gain something new. And once success becomes part of your identity, the next attempt stops feeling like a creative act or pursuit of a passion and new identity.....and starts feeling like a risk.
Book one was about possibility.
Is it possible to write a book?
Is it possible to become a bestseller?
Book two feels like proof.
And proof feels so so intense.
Because now it’s not just:
Can I write a good book?
It’s:
Can I do it again?
Can I do it better?
Can I live up to what people now expect from me?
Can I live up to what I expect from me?
Can I prove I'm not a one-hit-wonder?
That’s where I think so many ambitious people get stuck.
The first win gives you confidence.
But it can also quietly hand you a handful of new fears:
- The fear of not being able to repeat yourself.
- The fear of disappointing people.
- The fear that maybe the first time was a fluke.
So instead of creating freely, you start from a different place: protection.
And that is where great work goes to die.
Because the moment you make your next move about protecting your last success, you stop making bold moves.
You start editing too early.
Overthinking too much.
Hesitating before you begin.
Not because you aren’t capable.
Because now it feels like you have something to lose.
So how do we overcome this?
Keep reading.
♟️ YOUR TURN:
Here’s what I’m reminding myself in real time:
1. Treat the next thing as a practice, not a proof point.​
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The goal is not to prove I deserved book one.
The goal is to write the truest, sharpest, most useful book I can write right now.
And that's it.
2. Go back to process when outcome feels too heavy.
When my brain starts obsessing over lists, rankings, advances, expectations, and reception, I need to drag it back to what I can control:
Did I sit down today and write?
Did I make the work better today?
3. Don’t let success become your identity.
Success is something you experienced at a point in time.
It is not the full definition of who you are.
Because if your identity becomes “person who succeeds,” then every new project feels emotionally dangerous (and fucking exhausting).
4. Make room to be a beginner again.
Every new level requires being bad, messy, unsure, and inconsistent for a while. My son plays videos games and always gets frustrated when he moves to the next level because he dies a lot more while he's learning it. I have to remind him....
That’s not failure.
That’s the price of getting better at something.
And maybe that’s the hidden tax of ambition:
The more you win, the more you have to fight the urge to become careful.
Because careful is rarely where the magic lives.
So if you are staring at your next chapter, your next company, your next reinvention, and feeling weirdly scared because you’ve done well before....
You are not broken.
You are likely just experiencing the weight of having something you don’t want to lose.
But the answer is not to grip tighter.
It’s to loosen your grip on the outcome.
And return to the work.
Because the people who keep growing are not the ones who never feel fear after success.
They are the ones who decide that protecting the old win matters less than being brave enough to build the next one.
Would love to know if this resonates.
Have you ever felt more scared after success than before it?
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