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.

On August 2, 2016, I was laid off from my last corporate job at Fidelity Investments. I’d been there five years. It was a solid position, and on paper, things looked great. But under the surface, something else had been brewing for years.

I’d always had this quiet voice nudging me toward deep transformational coaching—toward helping others with the same challenges I had wrestled with. I’d done the training and the research. I’d made the plans. But I never took the leap.

Until I had to.

The Wake-Up Call

The layoff came with nine months of severance and a bonus payout. Everything I needed to start the coaching business that I have been dreaming of.

But here’s the part I still don’t like to admit. Instead of seeing it as an opportunity, my first instinct was fear. I needed to find another job—and fast! That’s what we’re conditioned to do, right? Security. Stability. A steady paycheck.

It became clear pretty quickly that a comparable job was not on offer. So I thought, maybe consulting?

For several months I had more conversations that went nowhere. But a close friend cut through the noise and asked me the question I needed to hear:

“What are you doing? You’ve been talking about coaching for years. This is your moment. Take it!”

She was right. And months after my layoff, I finally made the choice.

The Tool That Changed Everything: Pick Now

I now teach my clients a tool I call Pick Now.

It’s simple—but not easy.

We often wait for more clarity, more confidence, more data before making a move. But that fear you’re feeling? That hesitation? It’s not a red light. It’s a sign that you’re on the edge of something meaningful. It’s the last thing you feel before you take the leap.

You already know what to do. So do it. Pick Now.

When you choose—decisively—you invite momentum, clarity, and purpose to follow.

Everything wants these things before the choice. But you get them by makingthe choice.

(I’m convinced that this is why so many “side hustles” never really turn into anything. Mine certainly didn’t.)

What Happened Next

I didn’t pick right away. I was too scared! I did all the things—I hesitated. I tinkered. I dabbled as I looked in different directions.

Nothing moved until I chose.

Once I chose coaching—once I truly committed to it exclusively—everything started to change.

And I don’t just mean financially (though I now make more than I ever did in corporate).

I mean the fulfillment of working with amazing founders and CEOs. The joy of helping leaders scale without losing themselves. The pride in building something that’s mine.

The gratitude of making an amazing living working with others while working on myself.

All because I stopped waiting. And I picked now.

Pick Now. Then Pick Now Again.

I don’t want to suggest that you commit and you’re done. Far from it. The magic of Pick Now is in the compounding. In the power of developing the Pick Now muscle over time.

Every time you Pick Now it gets easier to Pick Now the next time. There is less fear, less hesitation, more excitement. And there is tremendous power in that.

It took a while (years, really) for me to Pick Now the first time. And my coaching business needed me to Pick Now again and again to truly get momentum. But now, every time I feel hesitant or stuck I know that if I just Pick Nowthings will get easer. The relief is palpable, the momentum unstoppable.

The same can be true for you.

If You’re on the Edge, This Is for You

Maybe you’re where I was in 2016. Sitting with a plan you haven’t activated. Knowing what you want—but not stepping into it.

Here’s my message to you: Pick Now.

Don’t wait for the fear to go away. Don’t wait for perfect clarity.

Pick Now. Take the step. Make the call. Launch the thing.

Do it scared.

Fear isn’t a red flag. It’s a green light. It means the only thing left is to take the leap.

Pick Now, and then Pick Now again, and again, and in a month, six months, a year—you won’t even recognize your life.

Does This Resonate?

If this resonates with you, I’d love to hear your story. What’s the thing you’ve been putting off? What would it look like to Pick Now?

And if you’re a founder wanting to explore this with other founders, DM me about in person event in Denver, October 20-21.

#PickNow #LeapOfFaith #Founder #ExecutiveCoaching