“Nothing Is on Fire. So Why Does Everything Feel Burning Hot?”

A founder writes in. The answer isn’t what they expected.

Welcome to the first edition of Dear Katie,

I’ve gotten some version of this message a few times this year already.
(I’ve anonymized and blended them into one letter.)

The Letter

Dear Katie,

I don’t even know if this is an ops thing or just… the job? But I’m tired, and I’m starting to feel kind of stupid that I can’t seem to fix it.

We’re truly not failing. We have customers. Revenue is up. The team is good.

I like them. I hired them because I trust them.

Somehow, I’m still involved in everything.

Sales pings me before sending things “just to make sure.”
CS asks if timelines are okay before they commit.
Product wants my take because “you’ve seen all the edge cases.”

Nothing is blowing up.
But everything feels… delicate? Like if I step away for a week, something important will quietly go sideways.

I keep telling myself this is just what this stage feels like. That it’ll calm down after the next hire. Or the next quarter. Or once things are more “settled.”

Then I think maybe I need a COO or a Head of Sales or a Head of Something!
That feels intense and expensive. And honestly, a little dramatic for where we are.

I can’t tell if I’m being patient… or just avoiding the fact that I might be the bottleneck.

How do you know the difference?

— Tired of Being the System

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My Response

Dear Tired of Being the System,

First: this is normal. Like REALLY REALLY normal.
Second: it’s not something you should just push through.

What you’re describing isn’t a leadership failure.
It’s what happens when a company outgrows founder-memory before it grows real operating clarity.

Right now, you’re the connective tissue.

You know what Sales promised.
You know what CS can realistically deliver.
You know which exceptions are fine… and which ones will come back to bite you later.

So capable, smart, people come to you because you’re the safest source of truth.

That’s rational behavior.

Where founders get stuck at this stage is assuming there are only two options:

• Keep holding it all together yourself
• Hire a full-time CXO, Head of X, VP of Y, and make it “official”

There’s a middle path most people skip.

Before you hire someone to own the system, you need help seeing the system.

That usually looks like:

• Mapping where decisions actually live (not where you hope they live)
• Naming the handoffs that quietly rely on you
• Turning founder judgment into shared clarity instead of private context

When that happens, two things shift:

You can finally breathe without feeling irresponsible.
And if you do hire later, you’ll make that decision from clarity instead of exhaustion.

If the company runs because you’re constantly translating, approving, and remembering, you’re not broken.

You’re just at the edge of your next operating model.

Shockingly, you don’t have to white-knuckle your way through it alone.

—

I’ve started opening a small number of advisory slots for founders in exactly this phase.
Not execution. Not templates. Just a place to think clearly and stop being the system.

If this letter could’ve been written by you, you know where to find me.