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

Taylor Swift has sold out stadiums, topped charts, and redefined the music industry. But her boldest move this year wasn’t a new album or a global tour. It was a podcast. Just last week.

Two hours, unscripted, in front of a live audience of 1.3 million. Her first time sitting down in that format.

She laughed, she teared up, she shared pieces of herself in a way fans had never seen. For someone who has carefully controlled her image for two decades, this was a leap into the unknown.

But here’s what makes it even more interesting: the host was her boyfriend. That choice mattered. It softened the downside risk—she knew she was stepping into a safe environment, not a perhaps hostile press. She picked a space where vulnerability was possible without being reckless.

But the podcast was live-streamed—no second takes. And The Heights podcast is no slouch, the top rated sports podcast on both Apple and Spotify and one of the top podcasts overall.

While there was risk, 400 streams later suggest it was a risk worth taking.

400 million potential customers for the new album she announced halfway through.

That’s the essence of Pick Now.

Taylor Swift didn’t wait until she had the “perfect” setting or a guarantee of how it would land. She chose a move that stretched her, but with enough guardrails to make the leap survivable. She picked—knowing full well it could expose her in ways that felt risky.

And the truth is, waiting would have only compounded the fear. Action is what dissolved it.

By Picking Now, she gained what hesitation never brings: clarity, momentum, and yes, relief.

The payoff? Her fans are more connected to her than ever. And she got exposure to a sports audience who is not her core fanbase. Not because she controlled the narrative, but because she let go of control. Because she chose courage over caution.

That’s leadership.

Most of us don’t face the glare of a global spotlight, but we do face decisions that weigh just as heavily in our world. We stall, thinking more time will reduce the pressure. In reality, it only increases it.

The fastest way out of a stuck place isn’t more information—it’s more motion.

One step forward.

One move that unlocks the next.

Taylor Swift reminded us: even the most polished, successful people still feel fear before a leap. What sets them apart is that they choose anyway—often by finding the version of the risk they can actually take.

What’s the “podcast” in your life—the move you’ve been avoiding because you can’t know how it will turn out?

And what’s the version of it that’s bold, but survivable?

Pick it. Now.

#PickNow #Founder

Want a short video explaining how you, too, can make your next bold move? Comment “Pick Now” below and I will DM you the link.

And keep an eye out for the Pick Now podcast, coming soon.