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.

We have a Turkish exchange student with us right now, and he’s a huge US movie buff.

To my surprise, he hadn’t seen any of the original Star Wars movies. One of my favorite hero’s journeys.

Of course we started with the original (now known as Episode 4). In rewatching it, one thing struck me.

When Obi Wan first asked Luke to join the rebellion, Luke instinctively said no.

The reasons that his uncle was keeping him from leaving to join the Imperial Academy (his responsibility to the farm, to one more harvest, etc.) become the very same reasons he says no to joining the rebellion.

He only leaves when his aunt and uncle are killed by the Empire and he literally has nothing left.

The greatest Jedi started out scared and small.

You, too?

I Had to Lose Everything, Too

I first wanted to leave my job and become a coach in 2011.

I felt called. But I didn’t answer the call until 2016.

Even then, I didn’t answer it voluntarily. I was laid off in 2016. My role was eliminated. I finally pursued coaching when it became clear that getting another job wasn’t going to happen.

Only at that point was I willing to fully commit. But what a journey since then.

This is my tenth full year coaching. I work with founders striving for purpose (and nine figures). I work with the identity crisis that comes after the exit. I coach one-on-one, I host retreats, I speak, I host a podcast.

None of this would have happened without that layoff in 2016.

Looking back it all fits. It feels like the universe has always wanted this, and more, for me.

And it still feels like I’m just getting started.

What about you?

What’s Your Hero’s Journey?

You might be a founder who sees the possibility of something more but has nothing left to give.

You might be a burned-out executive wondering why all the rules you followed never made you happy.

Your current life isn’t working. Your current identity isn’t working. The current version of your company isn’t working.

Another possibility shows up. Bigger. More meaningful. More aligned.

But you hesitate. It’s scary. It’s risky. You don’t know if it’s going to work, or how it’s going to work.

Will you slay the dragon? There’s only one way to find out.

Answer the Call

I recently talked to a leader who had just given a speech to his entire organization about the hero’s journey. He excitedly told me how well it had gone.

But he himself wasn’t taking the risks he was asking his people to take. His goals were ho hum, even as it was clear his people wanted more.

Was he willing to make a flowery speech? Yes.

But he was afraid to take the organization to the next level because he was afraid to take himself to the next level. He had no idea how to.

No one does.

It’s one thing to give a pep talk. It’s another entirely to step into the unknown.

Face The Trials

We love to watch others’ hero’s journey because it can give us the thrill without the risk.

Whether that’s Star Wars, Harry Potter, the Matrix or the Super Bowl.

These stories inspire us, but they cannot change us.

The actual journey? Facing your demons? Terrifying. But also necessary. At least if you don’t want to regret your decades-long slow decline into impotence and irrelevance.

You think you know what the learning will be. You think you can know in advance. But the only thing you can do is to put yourself in the arena, and embrace the learning that comes.

Those struggles will forge you into the person you are meant to become.

Your old identity will likely be burned away in the process. Because the very things that brought you to this point are keeping you from getting to the next one.

Who’s Your Villain?

Every hero needs a villain.

Who (or what) is your Darth Vader? Your Voldemort?

It might be a person. It might be a competitor. It might be a system.

You might have what Simon Sinek calls a Just Cause. A grand quest, a metaphorical castle guarded by dragons.

But it might also be an aspect of you.

For most people, the hero’s journey isn’t about defeating an outer villain.

It’s about overcoming an inner obstacle—the voice that has long kept us safe and small.

The voice telling you stories that for thousands of years kept your ancestors from dying but are now keeping you from living.

Listen to what that voice is telling you. Are you ready to stop believing it?

Two Demons, One Result

Everyone’s voice shows up differently, but it’s always recognizable.

Flavor One—Planning versus Haste

“I’m not ready. It would be foolish to rush this. I need more expertise. I need to check with one more person.”

Do you really need more time? Will more information actually help you? Or are you just scared? Take one small action. #PickNow. If you feel relief, or just the tiniest thrill, you’ll know you’re on the right path. The path of action over analysis.

Flavor Two—Gratitude versus Greed

“Things are really good right now. It would be greedy to want more. I have such a good life. Why would I risk it unless I knew this would work out?”

Yes, until your dull routine leaves you bored out of your mind and depressed. Yes, until, decades later, you regret all the things you never tried.

Most people have one or both of these voices in them.

Not only can you defeat them, you can liberate yourself and others in the process.

Return Changed

The new version of you doesn’t happen instantaneously. But it will never happen before you start.

The commitment can be instantaneous. But the journey, one action after another, can take years.

People think that you can change by yourself. But you can only be willing to BE changed. The circumstances you put yourself in and the people you surround yourself with matter.

Make sure the people you spend the most time with are challenging you, not holding you back. Make your move toward difficult things, not away from them.

Your willingness to go on the journey means everything to how you return.

Beyond Resolutions

New Year’s Resolutions last at most about two weeks. Why? Because they start with behavior rather than identity. Adding one more thing to an identity that is already stretched to the seams.

Want to be fit? Start with the identity of a fit person. What would a fit person do today? The fit body must follow. Every day you will get closer.

Decide to work out every morning when you love to sleep in?

You’ve probably already failed.

The Journey Never Ends

You will never get “there,” to some ideal identity in a future that doesn’t exist.

Because you’re always here and, in each moment there is something you can do better. The trick is accepting that. Embracing that without turning it into beating yourself up.

Continuing to get better is what we all strive for. But that never meant we were bad.

Shunryo Suzuki, the author of Zen Mind, Beginners Mind, might have said it best when he was addressing a group of his students.

“You are perfect as you are. And you could use a little improvement.”

That’s the paradox of the human journey.

Enjoy it.

When I launched my podcast, “Pick Now,” I thought it was about founders.

Leadership.

Better decisions.

After 14 long-form conversations, it’s becoming even more clear:

Every episode circles the same critical moment in a person’s life:

After the old way stops working—and before the new way feels safe.

Here are the five themes that keep repeating, no matter the industry, background, or success level.

Fear is the Signal You’re Ready

No guest waited until fear disappeared. Fear showed up with the decision. The ones who moved forward didn’t fix fear—they listened to what it was pointing at and committed, one small step at a time.

Waiting Costs More Than Acting

Every story has a quiet place where things get stuck: keeping options open, seeking more clarity, delaying the hard conversation. In hindsight, no one regrets acting too soon. They regret waiting too long.

Identity First, Then Strategy

Leaders don’t plateau because they lack tactics. They stall because the leader is still coming from an identity that no longer works—expert, achiever, safe pair of hands. Until that identity loosens (and expands), nothing new sticks.

Success Scripts Work—Until They Don’t

Wall Street. Military. Law. Tech. Entrepreneurship.

These scripts deliver results—until they start extracting more than they give. The breakdown isn’t personal failure. It’s expiration.

Freedom Comes from Commitment, Not Optimization

The people who look most “free” didn’t find better answers. They made cleaner commitments to a “just cause” that drove them. They picked, moved, learned, and adjusted. Analyzing feels useful. Hesitation feels practical. Optionality feels safe. But only commitment actually creates the freedom you’ve been looking for.

What Will You Create in 2026?

What can you learn from these founders that you can apply right now?

That’s what the podcast is really about.

Not being fearless.

Not getting it right.

It’s about acting before certainty shows up—and trusting that clarity follows movement.

After 14 founder interviews, that pattern is undeniable. And if you’re in that in-between moment right now…you’re not behind.

You’re right on time.

Let me know what you want to create in 2026. Let me know the version of you that’s no longer working.

And maybe you’ll be one of the interviews I’ll be talking about at this time next year.

Follow the Pick Now Podcast Here—

Spotify and Apple

#PickNow