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.

If you’re trying to grow a company, I can almost guarantee there’s a job you’re still doing that’s holding you back. Maybe you were great at it once. Maybe you want to prove you can still do it. But you’re no longer the best person. Admit it. You’re just getting in the way.

Time to fire yourself.

Jerry Jones Should Have (at Least) Three More Super Bowls

Look at Jerry Jones, the owner of the Dallas Cowboys. Last week, he pushed his best defensive player (“All World” edge rusher Micah Parsons) right into the arms of the team who keeps beating the Cowboys in the playoffs, the Green Bay Packers. Why? Because he refuses to fire himself from the role of General Manager. Every other NFL owner has a full time GM. Jones has insisted on running the Cowboys himself since 1989.

Yes, the Cowboys won three Super Bowls in the early years, in no small part due to the foundation built by his first coach, Jimmy Johnson. But here’s the scoreboard since 1996: no Super Bowls, not even an NFC Championship appearance. Coach after coach, player after player, same story. The bottleneck isn’t the team. It’s Jerry Jones. He wants to win it again, but this time he wants ALL the credit.

So year after year his teams come up empty.

Leaders do this all the time. We hold onto the thing we should have let go of years ago. We try to prove we’re still “the one” for that role. Meanwhile, the business stalls, morale suffers, and the opportunity cost compounds.

Where Are You Being Jerry Jones?

What role are you clinging to that someone else could do better? What’s your “Super Bowl” that you’re not reaching because you won’t let go?

Fire yourself. Hire greatness. Step aside and watch your organization take off. That’s another way to Pick Now—by letting others take both the limelight, and, when you win, the credit.

If you want to experience this with other founders like you, reach out about my Founder Event in Denver on October 20-21. We are currently sold out but I am happy to put you on the wait list and keep you posted about what is coming next. Just comment below or send me a DM.

#Founder #PickNow

In August 2024, Kelly Ortberg stepped into Boeing as CEO. The company was in free fall—just months earlier, a door had literally blown off a Boeing plane mid-flight.

He didn’t arrive with a 200-page plan or a dozen task forces. He didn’t wait for perfect clarity. He looked around, saw what needed doing, and started. He took the action he thought was needed. Then did it again the next day. And the next.

A year later, Boeing is almost unrecognizable: profits up, revenue up, quality up, even wages up. The stock is up 50%.

That’s the power of momentum. Of picking what you know you need to do, day after day after day.

You don’t need to know how it all works out—you just need to move. Small, consistent actions compound into transformation.

What’s Your Transformation?

So here’s the question: what part of your business (or life) would be unrecognizable a year from now if you simply acted on what you already know needs doing—day after day after day?

Pick Now.

#PickNow #Leapoffaith #Founder