It was managing everyone else around the business.

“How’s it going?”

“What do you think this month will look like?”

“That must be really scary. I could never do that.”

Family. Clients. Trusted friends.

All framed as concern. But really? They wanted me to manage their nervous systems. And it was exhausting.

I only realized recently that I don’t have to do that.

I grew up thinking it was my job to keep everyone calm. To be the steady one. The reasonable one. The one who had it handled.

I got very good at it. So good that people commented on how calm I was.

I wasn’t. (Performative calm is absolutely a thing.)

During the day, I was mostly fine. At night, I woke up in a sweat. About the business. And about what I would say about the business.

How honest I could be.

Who I could actually help. Who I couldn’t. How many clients I needed. How close the math really was. What would happen if the math didn’t work out.

Same thoughts. Over and over and over.

Some of this is our human psychology. At night, fear runs the prison with no guards.

But a lot of it?

Optional.

When we are both present, I know I can help you. You know it too.

What you’re feeling isn’t confusion.

It’s just fear.

And the places you’re afraid to look?

That’s exactly where the work starts.

Neo isn’t hiding who he is.

He’s already looking.

By day, Thomas Anderson does what’s required.

Keeps the job. Stays inside the lines. Functions.

By night, he searches.

Follows a signal he can’t name. A person he barely knows. A quiet hope that there’s a truth that can save him.

The Matrix Isn’t What You Think

The Matrix doesn’t trap you with comfort.

It traps you with good enough.

Bills paid. Respect earned. People depending on you.

Just enough to postpone the real questions. Just enough to avoid the real risk.

Don Draper builds a mask to survive the past.

Neo is willing to leave because his future won’t leave him alone.

The exhaustion doesn’t come from effort. It comes from running two operating systems at once.

One self that keeps everything working. Another that knows working isn’t the same as living.

Morpheus Doesn’t Have Answers

He offers only the truth: that “Thomas Anderson” is a simulation of a life.

Morpheus doesn’t wake Neo up. He finds him already awake, and tired of pretending.

Neo is willing to leave numb safety for dangerous truth.

Not because he’s certain. But because his responsible self and his searching self can’t stay separate anymore.

Because good enough never actually was.

Nothing Is Wrong With You

If this is landing, nothing is wrong with you.

You’re not failing. You’re already halfway out.

Most people don’t talk about this until it starts costing them sleep. I didn’t.

The only question is which direction you head next.

At first, the mask is useful.

It keeps you safe.

You learn who you need to be. What works. What gets approval, momentum, authority.

You get good at it. Even with time, excellent.

That’s Who Don Draper Is

Not a fraud. Not an imposter. A survivor.

Underneath his suit is Dick Whitman—the poor kid, the unwanted kid, the one who learned early that being himself wasn’t safe.

The world rewards your Don Draper.

Success doesn’t just validate the mask. It makes it permanent.

Every win reinforces the same rule:

I can never be Dick Whitman again.

This is where many high performers end up.

They perform flawlessly while something underneath goes numb.

Late in Mad Men, Don takes his kids to the house where Dick Whitman grew up.

Dirt, poverty, and (finally) the truth.

He doesn’t explain himself. He lets himself be seen.

Most founders don’t burn out from effort. They burn out from living on top of the part of themselves they’ve disowned.

Performance takes energy.

Exile takes even more.

Who Are You (Really)?

If this is landing uncomfortably close, nothing has gone wrong.

You’re standing in the place where the mask still works.

But you’re the only one who knows what it’s costing you.

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.