The Success Trap

It seems like my meditation last week on identity and growth struck a chord, so here’s another personal thread I’ve been pulling at…

We don’t talk enough about how fragile success really is.
Not the business metrics… those are obvious.
I mean the internal kind.
The kind that creeps in quietly once things start going well.
The kind that convinces you that what worked yesterday must be who you are tomorrow.
The kind that gives you security that your thinking of today will keep resonating tomorrow and tomorrow.

I kept circling this thought while editing this week’s Thinking With Mitch Joel conversation with Ranjay Gulati.

Rajay is a Harvard Business School professor and one of the world’s most cited scholars on leadership, strategy and culture who just published the book, How To Be Bold – The Surprising Science Of Everyday Courage.
His work on bold leadership pulls apart the myth that success makes us stronger.
Often… it does the opposite.

Success narrows us… this was a surprising realization for me.

It tightens the boundaries of who we think we’re allowed to be.
It makes us cling to playbooks long after the game has changed.
It rewards predictability, even when the world is begging us to evolve.

It’s strange… because we imagine success as expansion.

But for most leaders, it becomes confinement… comfort.
Because once things work… you start protecting the version of yourself who made it work.
You stop experimenting.
You stop questioning.
You stop listening as widely as you used to.
You start believing your own mythology… the one others repeat back to you because it’s easier than challenging your identity.

Success becomes a shell… and over time… shells harden.

Ranjay talked about this trap with a kind of precision that made me uncomfortable in the best way possible.
He called out how leaders slowly become risk-averse, not because they’ve lost courage, but because they fear losing the story of themselves.

We like to think failure humbles us… but success does too… just more quietly.

Success creates expectations.
Expectations create fear.
Fear creates rigidity.
And rigidity is the beginning of decline… personally and organizationally.

It’s wild how often leaders stop growing long before the business does.

They keep scaling the company… but not themselves.
They keep adding capabilities… but not perspectives.
They keep optimizing performance… while starving intuition.

That’s the real fragility of success… it tricks you into thinking evolution is optional.

Ranjay reminded me that boldness isn’t a trait… it’s a practice.
A willingness to stretch beyond the identity that success carved for you.
An openness to hearing truly diverse voices (from the newbies to the retired).
To disappoint the expectations others built around you.
To risk being misunderstood again… like you were at the beginning.
To remember that curiosity, not certainty, is what got you here.

But here’s the nuance I keep coming back to… staying bold isn’t just about pushing through fear… it’s about keeping yourself fresh.

Fresh in your thinking.
Fresh in your learning.
Fresh in your willingness to absorb ideas from people you don’t expect: peers, competitors, critics, even those younger or less experienced than you.
The leaders who stay relevant aren’t just courageous… they’re students… continuously… quietly… habitually.
They’re the ones who still read deeply, ask naïve questions, sit in rooms where they’re not the expert, and allow themselves to be reshaped by perspectives that contradict their own.

Maybe the real test of leadership isn’t how you handle failure.

Maybe it’s whether success makes you bigger… or smaller.
Whether it keeps you open… or makes you guarded.
Whether it makes your mind more porous… or more calloused.
Whether it expands the circle of people who can teach you… or shrinks it to those who only reinforce the success you already had.

So here’s the question I’ve been sitting with since the recording:

When success arrives, do you expand into the next version of yourself… or do you shrink to protect the old one?

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