Scaling Character In The Age Of Scale

It’s one thing to scale a company.

It’s another thing to scale your character at the same time…
And in this AI world, it might be the most important conversation we’re not having?
We celebrate the rocketship… the valuations… the growth hacks.
We celebrate the leader who raises a round on Monday and doubles headcount by Friday.
But we whisper (if that) about what really cracks most organizations: when the humans at the center can’t keep pace with the thing they’ve built.

Scaling revenue is a process… scaling character is actual chaos.

Because growth isn’t just the sales that are coming in.
It’s more meetings where your words land harder than you intend.
It’s more employees watching every move for signs of fatigue, hypocrisy or control.
It’s much more feedback loops with some disguised as praise, some dressed up as insubordination.
It’s the widening gap between the leader you think you are… and the leader the company suddenly needs.

I’ve felt that lag myself.

The business evolves faster than the operating system inside me.
One moment you’re a scrappy individual contributor who thrives on hustle.
The next, your team needs someone patient enough to listen, generous enough to coach, calm enough to hold space when things catch fire.

And here’s the dirty little leadership secret few will speak of: most leaders don’t make that pivot fast enough… if ever.

That idea hit me hard when I was editing this week’s Thinking With Mitch Joel podcast with Margaret Andrews.
Her book, Manage Yourself To Lead Others, explores this gap between business growth and personal growth, and it stuck with me.

That lag (or lack) destroys more companies than competitors ever will.

We love to say leadership is lonely.
I don’t buy it anymore.
Leadership isn’t lonely… it’s disorienting.
It’s standing at the front of a room, realizing the company has scaled beyond the version of you running it.
And unless you can scale your character with the same discipline you scale your product, you’re leading with yesterday’s software.

And yesterday’s software crashes… always.

This isn’t therapy-speak.
It’s not about being “nice.”
It’s about survival… yours and the company’s.
They’re not just buying into your model.
They’re buying into your temperament.
And temperament doesn’t scale by accident.
It scales by choice… by design… by the willingness to stop chasing external growth long enough to ask: What kind of leader is this company asking me to become?

Businesses don’t fail because the market shifts… businesses fail because the leader refuses to shift.

So maybe the more honest question isn’t “How fast can we grow?”
It’s “How fast can I grow into the person this growth requires?”
If you’re not scaling your character, your company is just running away from you.

Are you growing your character as fast as you’re growing your company?

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