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

You’ve got an eight-year-old inside you who’s scared to death.

Who was taught at some point that certain feelings aren’t safe. And who might have even lost the ability to feel them along the way.

It took me decades to see this but you can see it in a moment or two, if you have the courage to look.

What Are You Feeling Right Now?

Take a moment to ask that question. To see what you feel in your body. Just that, without going into any story to justify why you feel that way.

Tension? Warmth? Tightness? In your chest, your gut, your throat, your shoulders?

What emotions do you feel? Happy? Sad? Scared? Angry? Excited? Again, without a story. Just the pure emotion.

Take a moment and see what you find.

A lot of the high achievers I work with come up empty at first. They can’t identify an emotion or even a sensation in their bodies.

This doesn’t mean that there’s something wrong with you. It means that at some point you learned that one or more of your feelings aren’t safe.

I learned it, too.

Most very high achievers and very low achievers share something similar.

They numb themselves to the thing they most need to feel.

The addict uses substances. The achiever uses activity.

And we praise one and shun the other.

What Are You Afraid to Feel?

I’ve always been much more comfortable with happy feelings. If I move toward something that feels like anger, or sadness, I will quickly tell myself a happy story (like, “I’m so grateful because it could have been much worse”).

It took me a long time to see why I was avoiding feeling down.

I grew up thinking I needed to manage my mom’s anxiety. Many of my emotions quickly overwhelmed her and she took that out on me, mostly through shame. Over time I became very good at managing my emotions, even though I could never manage hers.

I was talking with another entrepreneur yesterday who said he would rather feel fear than sadness or anger. When he feels uncomfortable, he creates work projects to distract him.

I can relate. I’ve done the distraction thing with a divorce, a layoff, several career changes and two moves across the country.

Stay positive. Focus on the opportunity. Move forward.

But doing that kept me stuck in achievement mode, and exhausted me in the process.

What Are You Willing to Feel?

I’ve been practicing meditation for almost thirty years and I’d guess the first two decades were about escaping from my feelings rather than embracing them.

Meditate, work hard, focus on the positive.

You might have some highly evolved strategies to avoid feeling, too.

Those strategies have brought you a lot of success. But now those same strategies are keeping you stuck. Keeping you on the path that brought you here, to this very article.

What it Feels Like When Something is Wrong

I just got off the phone with a man who built a very successful company and now is selling off the pieces because he can’t handle all the stress.

He’s moving away from the feelings rather than feeling them. And it’s holding him back.

He has a story that he can only be successful to the extent that his anxiety will allow him to.

Like an invisible fence warns a dog, the anxiety warns him that he is close to his capacity.

Have you ever seen a dog that bursts through the invisible fence to discover the freedom on the other side? How it initially tries to get back inside, and then realizes, “I can go anywhere!”

That’s what’s waiting if you can just fully feel your difficult feelings, and not be prisoner to them.

On the Other Side of Feeling

The thing that you are afraid to feel isn’t nearly as scary as you’re making it out to be.

If you’ve been scared of it a long time, you might not be able to feel it all at once. And if it’s related to serious trauma (physical violence, emotional abuse, PTSD) by all means seek out a trauma-informed therapist, or a qualified somatic practitioner.

But believe me when I say, with the right guidance, there is freedom on the other side of feeling your fear.

Being able to survive the thing that your 8-year-old is telling you is unbearable.

Again, this is deep intense stuff. But this is the work. This is the path to what you really want.

One Small Step Forward

When you feel stuck, when you know you need to move, but don’t quite know how, you can Pick Now.

You can take one small step and see what it brings up. You can test. You can refine.

You can choose the way forward. Again and again and again.

Want a quick way to get going? Try my Pick Now Decision Sprint. And let me know what you think.

https://tinyurl.com/PickNowSprint

#PickNow

Most leaders don’t need more frameworks.

They just need better questions. Questions that cut through the noise. Questions that expose the truth you’ve been dodging.

Do you want to stop building yet another week of your life on top of assumptions that may not even be real?

Here are 10 questions I use with founders when they’re spinning, overwhelmed, or stuck in “figure it out” mode.

They create clarity uncomfortably fast.

If you’re brave, use them daily for a week. If you’re really brave, notice which one you avoid.

That’s the one that will change your life.

1. What am I pretending not to know?

Most indecision is just fear disguised as practicality.

You already see the move. You’re just scared of the cost.

(Use my Pick Now tool for this one—https://tinyurl.com/PickNowSprint)

2. What am I trying not to feel?

Scared? Inadequate? A lot of overachiever mode is about pushing those feelings away.

What if you were to let yourself feel whatever you need to feel, to let it pass through you without resistance?

What’s on the other side? What could you do then? Who could you be then?

3. If I wasn’t trying to impress anyone, what would I choose?

Approval is a hell of a drug.

Freedom is even better.

What do you want just because you want it? Not because it gets you something else?

4. Where am I suffering today that is entirely optional?

Shockingly often, the answer is: “Almost everywhere.”

Suffering is the tax we pay for an outdated identity. Notice where it’s happening to start to level up.

5. What’s the fear underneath the fear?

The surface fear is never the real one.

Underneath “I might fail” is usually “I won’t be enough,” or “People might laugh at me.”

If you can let yourself feel that, you can change everything.

6. What decision keeps returning to me that I still haven’t made?

The truth follows you.

It taps you on the shoulder until you pick.

If you keep seeing the same type of person or same type of situation, ask what you need to learn to get past it.

7. If this were easy, what would I do?

Ease isn’t laziness.

Ease is intelligence.

Your nervous system knows the shortcut your ego won’t take.

8. What’s the smallest action I can take that changes the trajectory?

Big moves overwhelm people into inaction.

Small moves, over time, change lives.

9. What desire have I been suppressing because it feels “unreasonable”?

The unreasonable desires are the real ones.

Everything else is conditioning.

What are you pursuing—what you want, or what you think you can have?

10. What will future me thank me for doing in the next 24 hours?

A direct line to the life you say you want.

Future you is already waiting, already watching, ready to offer advice any time you like.

And cheering for you every step of the way.

Try This Experiment

Pick one question each morning.

Write the answer without editing yourself.

Then take one tiny action based on what you discover.

This is how extraordinary futures are created — one honest question and one small step at a time.

And here’s that Pick Now tool again—use it whenever you can and watch your life change.

https://tinyurl.com/PickNowSprint

#PickNow