When I’m talking with a founder about working together, the conversation feels alive— creative, open, full of possibility.
It might start with what’s getting in the way, but it quickly turns toward what could exist instead. A future they haven’t quite allowed themselves to imagine yet. I see them lean in. I feel their energy shift. (Mine, too.)
And then I ask—
“Do you want to hear what this would require?”
The Moment Nobody Talks About
Up to that point, something honest is happening.
We’re talking about what they want to create. What no longer fits. What they’re tired of carrying. What they’ve outgrown but haven’t yet released.
There’s often relief there. Sometimes even excitement. The sense that something true is finally being named.
Then I lay out the commitment. The fee. The investment of a year. The two full days up front.
And something subtle, but unmistakable, happens.
Not a reaction. More like a withdrawal.
A pause. A nod. A question about structure or timing.
On the surface, everything still looks composed. Professional. Reasonable.
But underneath, the attention has shifted.
What was present turns inward. What was curious becomes careful. What was open starts organizing an exit.
I don’t interrupt that moment.
It’s doing important work.
What Begins to Move
What comes next almost always sounds responsible—
“I’ll have more time next quarter.”
“I need to see how a few things shake out.”
“I want to be thoughtful about this.”
“I need to make sure the timing is right.”
These aren’t excuses. They’re familiar pathways.
Most of the people I work with have been using versions of these sentences for years—sometimes decades—to navigate decisions without fully entering them.
These words help them stay functional. Respected. In control.
But each sentence also postpones things that matter.
Conversations that should have happened earlier. Endings that linger long past their usefulness. Choices felt clearly, then delayed until the cost of not choosing becomes unavoidable.
Not because they don’t know.
Because knowing is inconvenient.
And because it’s always easier to distract yourself than to feel what’s actually happening.
The Cost You Don’t See
The investment I ask for lands all at once. The cost of delay accumulates.
- Keeping responsibilities that you’ve mastered but no longer respect
- Making decisions that feel stable, but keep you small
- The low-grade fatigue even when things are “working”
- The voice that tells you it’s greedy to want more
You might be lucky. It might not touch your health or your relationships. You might keep it contained enough to keep showing up for your family.
But over time, something else erodes.
You stay responsible. Competent. Reliable.
And somehow, no longer fully alive.
You start worrying more and more about smaller and smaller things.
For the Founder Who Has Already Exited
The money is there. The pressure is gone. The calendar finally opens up.
And yet, something feels flat.
Not unhappy. Just unanchored.
You thought the exit would resolve the tension. Instead, it removed the structure that had been hiding it.
Without the company to organize yourself around, old questions resurface:
Who am I now? What actually matters? What do I want when no one needs anything from me?
You may fill the space quickly—boards, investments, advisory roles, impressive projects.
You may even start another company rather than face the quiet.
But underneath, you realize:
The exit didn’t solve anything. It just made clear what doesn’t work.
For the CEO Still Scaling
Revenue is climbing.
Headcount is increasing.
Decisions carry real consequences now.
More people, more families, more weight.
You’re needed everywhere.
Admit it, this is what you wanted. You just couldn’t know the cost.
Your days are filled with meetings where no one tells you the truth and everyone expects you to have the answers.
You keep telling yourself you’ll slow down once this phase passes.
But with each new level your grip tightens.
Somewhere along the way, leadership becomes less about you choosing a direction and more about holding everything together.
The Insight
At some point, you know. And you know you know.
This matters.
What follows isn’t confusion. It’s avoidance.
The old playbooks start running. Planning. Practicality. “Let’s revisit this next quarter.”
That part of you has done a lot.
It’s also deciding far more of your life than you ever intended.
Why We Begin by Stopping
We start with at least two uninterrupted days together.
You can’t see the machinery clearly until you step out of it.
When you’re in motion, almost everything can be justified. Delay becomes prudence. Discomfort becomes timing.
When movement stops, those translations fall apart. Patterns become visible. Truths stop being negotiable.
Nothing dramatic happens. You just finally let yourself see more clearly.
And once you see, you can’t unsee.
What the Year Actually Demands—and Delivers
When you return to your life, the same decisions keep showing up.
Some consequential. Some ordinary.
All of them carry weight.
Each invites the same familiar move. Back into the identity you know so well.
The capable one. The steady one. The one who bears the pressure. The one who waits for clarity. The one who waits for clarity.
This work isn’t self-improvement.
It’s contact.
Seeing the moment as it arises. Feeling the pull to retreat.
And choosing—not heroically, not impulsively—but honestly.
At first, it feels exposed. Unfamiliar. Even a little scary.
Eventually, it feels like relief—not the soothing kind, but the honest kind.
You become who you’ve been all along.
If This Is Stirring Something
Most people won’t allow themselves to seriously consider working with me.
They’ll feel this moment—and keep moving.
Not because they’re wrong. Because postponement has worked well enough so far.
The people who don’t move on are the ones who’ve begun to feel the accumulation.
They know what they’ve been giving up—not all at once, but slowly. They know the cost of choosing familiarity over truth. They know how often “later” has quietly become “never.”
If you’re still reading, you’ve been standing at this edge longer than you admit.
And you already know what happens next.
