If you’ve ever hiked in the mountains, you’ve probably hit a false summit. From below, you’re sure you’ve spotted the top. You push hard, heart pounding, legs burning, only to arrive and realize—you’re not there yet. The peak is still further on, hidden until now.

In business and in life, the same thing happens.

At a recent weekend on a Colorado ranch, I spent time with a group of founders who had already reached what most people would call the summit. They had sold companies and along that had gotten validation, recognition, and in many cases, a lot of money. And almost to a person, they told me some version of this:

“I thought it would finally make me feel like I was enough. Instead, it was the opposite. After a few days, I fell into a valley of despair. Disillusionment. Who am I now? If this isn’t it, what is?”

That’s the sting of a false summit. You think the climb is over, only to find a whole new stretch of trail you hadn’t planned for. And it’s overwhelming.

The financial success is real, and it matters. It buys freedom from: freedom from financial worry, freedom from needing to work again, freedom from the stress of survival. All of that is worth celebrating.

But it’s only one layer.

The deeper, more enduring freedom is freedom to—

• Freedom to say what you truly feel.
• Freedom to do what you actually want to do, to create what is in your heart, instead of what others expect.
• Freedom to be more, or just to simply be.

At our core we are infinite creativity. Most of us use that creativity to prove ourselves, or to fight against something.

I know for many years I was so attuned to what others wanted, that I had a hard time accessing what I wanted.

After doing all the things I was told would make me happy and still feeling empty, I began to see that the freedom I wanted wasn’t outside me, but inside. That I could free myself of the prison of others’ expectations. The prison that I had actually built.

You have built some version of this prison, too, and you have always had the key.

When you see you have always been free, you don’t stop creating. But you do create from a different place—one that isn’t about proving, but about expressing.

Whatever you call that—freedom, or mission, or purpose—is the real summit you’ve been looking for all along.

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Do you recognize any “false summits” in your own journey? What looked like the finish line, only to reveal itself as just another ridge on the climb?

Two weeks ago, Charlie Kirk was killed in a tragic act of violence.

In the aftermath, I started paying attention to Charlie Kirk in a way that I had not before. Obviously, there are wildly different perspectives on his views and his passionate defense of them.

I noticed, however, that there was agreement from both sides on one particular quality that he seemed to have no matter who he was talking to.

Over and over, both his supporters and his critics have said the same thing: when you spoke with Charlie Kirk, you felt listened to. You might not have walked away in agreement, but you walked away feeling heard.

That’s a rare quality. And whether you agreed with Charlie Kirk or thought his beliefs were abhorrent, that quality matters.

Does Your Team Trust That You’ve Got Them?

As a leader, you’ll make choices your team doesn’t like. But if your people believe their perspective was genuinely considered, they’re far more likely to stand with you. And if they sense you are open to change—curious enough to weigh new information, even if you don’t ultimately change course—that trust only deepens.

Charlie Kirk rarely shifted his public stances, but he left behind an example of what it looks like to make others feel heard. Like him, you may have principles that you are not willing to compromise on, and when you can explain those you will attract people who agree with and will defend those principles.

There are many decisions in running a team or a company that do not rise to that level. Where your team has information, or perspectives, that you do not have access to. When you can be genuinely curious, and willing to change your mind, your leadership is more powerful whether you change your mind or not.

That clarity doesn’t stall in indecision. It moves.

Get Input, then Pick Now

Leadership isn’t about waiting for perfect clarity. But it is about considering different perspectives. It’s about gathering input, listening deeply, and then making the call. Not just once, but again and again. Each pick builds momentum. Each pick shapes the future.

Curiosity. Listening. Decisive action. That’s how leaders pick now and keep building forward.

When was a time when you were genuinely curious, and how did it impact your team and your leadership?

A founder recently told me she was playing four-dimensional chess—trying to think five moves ahead, mapping out every scenario before making a move. She believed if she thought hard enough, she could figure it all out in advance.

Here’s the problem: that won’t work.

You Can’t Know in Advance

Have you ever rehearsed a conversation in your head, only to have it take a sharp left turn 15 seconds in? That’s every difficult conversation I’ve ever had. And it’s also what it’s like to run a company.

You can’t know how everything is going to unfold. You can’t plan for every variable. So stop trying.

Here’s what I do know—something unexpected will show up. And in that moment, you will figure it out.

Whether it’s having a difficult conversation or running a company, that capacity is your superpower.

But You Do Know the Next Step

You already know what to do next. Sure, maybe you’ve been avoiding it, thinking that time or analysis will give you more clarity. But chances are you’re just scared.

Do that thing.

See what happens.

Let the feedback—data, reactions, direction—come back to you.

Then make the next choice.

And then the next.

Don’t Wait for the Perfect Choice. Just Make the Next One

Running a business isn’t about perfection. It’s about momentum. It’s about stacking small, timely decisions and seeing where they lead.

Waiting doesn’t reduce the risk. It just compounds the stress. Action brings relief and clarity.

So quit thinking you can figure it all out before you make the first move. Make a move and see what happens. Over and over. Soon, you will find you have built something extraordinary.

What’s something you’ve been waiting for that you could start today?

Fifty years ago, Bruce Springsteen was at a critical moment in his career. His first two albums were critical successes but commercial flops. His key promoter at Columbia Records, Clive Davis, had just been fired. Columbia execs, eager to distance themselves from the flashy and opinionated Davis, were no longer in his corner.

The next album was make or break. Bruce took 14 months to record it, obsessing over every detail. Make it great or you’re fired. That’s what Bruce felt.

Does that sense feel familiar to you?

Bruce and his producers finally finished re-recording things because they had concert obligations. They celebrated completing the project. Yet when Bruce heard the first pressing, he panicked: “This is a piece of shit—Maybe we should just start over.”

Imagine if they had.

His producer, Jon Landau pushed back. He didn’t dismiss Bruce’s fear—he reframed it. He talked about all the choices they had made in the pursuit of perfection. He talked about how proud he was of Bruce, and said that the album was truly excellent.

But that didn’t change Bruce’s mind. Instead, it was Jon Landau talking about the next time.

The conversation isn’t over, Bruce. There will be another album.

In other words: you don’t need to get it perfect this time. You just need to put it out there. You just need to keep trying, over and over.

Born to Run became a rock classic. And Bruce almost buried it.

The Role of the Advisor

Fear convinces us to retreat. Trusted advisors remind us that the fear isn’t the end of the story. Advisors don’t eliminate the fear; they normalize it.

You can feel the fear and do it anyway. In fact, you have to.

Jon Landau wasn’t just polishing tracks—he was coaching Bruce to release something he was sure wasn’t good enough. The same thing happens in business. Founders hit the wall of “not good enough” every day. And left to themselves, many will stall, revise, or hide.

The right advisor doesn’t let you. They remind you the conversation isn’t over. They help you see that clarity doesn’t come before the decision—it comes from it.

Pick Now

If you’re waiting for the fear to go away, you’ll wait forever. Fear isn’t a red flag; it’s a green light. It means you’re standing at the edge of growth.

The lesson of Born to Run isn’t about perfection. It’s about releasing something when you don’t feel ready. About having someone beside you who believes in the work, even when you don’t.

So: what’s your Born to Run?

What’s the thing you’re scared to put out there? Whether that’s a software product or a risky acquisition, you are going to feel doubts.

Get it good enough and then get it out there. Learn from the result and do it again.

Bruce Springsteen has done 18 studio albums since Born to Run.

Not one of them is perfect.

You don’t need it to be perfect, either. You just need to Pick Now.