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

This week I focus on the most powerful things I’ve learned in 28 years of helping myself and other humans make big changes in their lives. (The first time I managed people, in 1998, I created a mission for myself. It was, “To inspire others to go beyond their own expectations.” I’ve been doing it ever since.)

If you’ve been reading my work, this list won’t necessarily be surprising. But the order might be.

A trigger warning going in. You might think that some of this sounds like “spirituality,” and that therefore it’s not appropriate for work. But what I’m pointing at is some of the most fundamental truths about our human existence, and they are truths that we have a habit of missing or avoiding entirely. To see this makes a huge difference in both our capacity to make change and our ability to experience fulfillment and connection during our working hours.

There is something about asking the bigger questions that gets us better answers. And there is something about having help that allows us to go deeper.

For an opportunity to work with a committed group of people as you create your own massive change, see the calendar link in the comments.

You Must First See Who You Really Are

Who are you, really? What is it that is looking out through your eyes? This is the real you. Not all the stuff you have made up about you, that you have believed about you. The thoughts about your body, about your story, about your abilities and talents and limitations. The thoughts that you’re a fraud or that you’re not enough or that your parents will never accept you.

All of those are just thoughts. And when you see that, when you realize that your experience of the world is 100 percent made of thoughts that come and go, you begin to get a lot less attached to any thoughts you happen to have. They seem lighter. Less serious. Less important.

You begin to see the difference between the things you habitually think, and the things you simply know. The things that you make up as useful, and the things that emerge, beyond the words, between the thoughts that have taken up so much of your time and energy.

For me, really seeing this took a long time. But when I got it, it changed everything. Because I was so much bigger, so much more capable than what I thought I was. Everyone is! And I’ve gotten better and better about pointing it out to other people because seeing it makes such a huge difference.

That said, some things–experiences from childhood, stories that carry a lot of emotion with them–can look particularly real. They can be hard to let go of. They typically show up as either bodily sensations or as the metaphors that we see the world through–the rules about life that we assume are true. They do need some special care, beyond the scope of this article, but with a little love, attention, and forgiveness, they too can fall away.

You Must See What Your Really Want

If you are like most people, the vast majority of what you have said you wanted to this point in your life has been one of three things–

First, what you thought you could have.

Second, what you thought others expected of you..

Third, what you thought would fix the bad thoughts you have about yourself.

All of these are made up. I actually asked one of my clients to ask his wife and kids what they wanted, and he was shocked when they said “more time with you,” and not the lifestyle he was spending all this time working to provide for them.

But the third one is my favorite because it’s so hilarious when you really see it. We make up rules like “I will be successful when,” or “I will know I am enough when,” and then not only judge ourselves for not meeting the rules, but totally miss that we are the ones who made them up.

(Somewhere, I was taught that beating myself up is a helpful self-improvement strategy. It’s not.)

When you see this is all the things you have called success are made up, that the things we thought would make us happy are just thoughts that come and go, what’s left?

There is a deeper knowing, a deeper desire, even, that emerges when you stop believing what you think all the time.

Pure. No reasons, no apologies. Patient, quiet, waiting. The still small voice that keeps reminding you.

THAT is what you want. The thing you want that you can’t explain. The thing you want just because you want it.

Often, that thing is a little bit scary, too. That’s why you resist.

It’s still scary for me at times. It seems like life wants me to create things that I don’t have any chance of creating. To say things I’m scared to say. To point out truths (like the ones in this article) that so many of us spend so much time avoiding.

But there it is. And here I am, bringing this into the world and, much to my own amazement, building a successful business doing it.

What would happen if you followed that quiet knowing?

You Must Be Who You Need to Be to Get What You Want

This is a HUGE leverage point, but even more powerful when you see that your very identity is made up in the first place.

We cannot get anything that we can’t conceive of having. Or that we think would be bad, or greedy, or selfish to have.

This is, for example, why so many heart-based entrepreneurs struggle with money. Because they want to do good and yet they believe they will be bad people if they are paid (too much) money for it.

Money is just a tool. It’s just stored energy. How you use it is completely up to you. I can’t think of a scenario where having less of it is better than having more of it.

Would you ever say, “I feel bad because I’m so energetic today”?

We do the same kind of thing with many aspects of this story you call your identity.

Until we see it’s not solid, it is very difficult to change. But once we see we are not an “introvert,” we are not a “procrastinator,” we are not “focus-challenged,” then we can see that we can make up our identity as anything that is useful to us in getting what we want.

One of the first things I realized as a coach was that I often needed to say things that were uncomfortable. So I became the one who would say uncomfortable things. And in doing that, I became a better coach. Because uncomfortable things were, to my surprise at the time, embraced. And soon I was incredibly comfortable saying what for most people would be incredibly uncomfortable. Because it was in service to the person in front of me.

I became the person I needed to be to do what I needed to do.

You Must Take Committed Action

You can BE whoever you want. In a split second. A moment of insight, of seeing a truth you didn’t see before, can change everything.

But if you want to create material things in the material world, you have to take action. Creating in the world means taking action. And it means being COMMITTED to that action. To becoming the person who will take that action. Over and over.

I was talking with one of my clients who compared it to martial arts. Yes, you can see the possibility of becoming a black belt. You can bring that into your identity (“I am becoming a black belt”) instantaneously. But the process of becoming a black belt in the world is the process of doing the things that you need to do to become a black belt, over a period of years, day after day after day.

Doing the things that you need to do to become a black belt. At first, you are doing it because you are on the path to become a black belt. You are trusting the path, even though it seems like you are a long ways away. And then a moment comes when you believe. You ARE the path. Becoming a black belt becomes inevitable.

And then, only after you have become a black belt in your mind, in the identity that you have created for yourself, do you become an actual black belt in the physical world.

That is what the creating path looks like. Committed action, over and over.

For most people, taking that committed action is much easier when the identity shifts first. And shifting the identity, coming from who you need to come from, is much easier when you see that your entire identity, your entire world, is made up of thought.

The Simplest Path to Create Massive Sustained Change

This, then, is the simplest path to sustained change. Not necessarily easy, but deceptively simple.

First, see that your experience of the world is 100 percent internal, 100 percent of the time. See the implications of that, including the fact that your identity is made up, too. See your habitual thinking begin to fall away in that recognition. See and experience the radiant silence behind it.

Second, see what you really want, what you desire, what emerges from that radiant silence. See what you want just because you want it, full stop.

Third, see who you need to be to create what you really want. Step into that identity. Create the habits that a person with that identity would have.

Finally, take committed action, over and over if necessary, until the result you seek emerges in the world.

I will close with one of my favorite quotes, from William Hutchison Murray in his book, “The Scottish Himalayan Expedition,” published in 1951. Forgive the gender-specific language—

“Until one is committed there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative or creation, there is one elementary truth…that the moment one definitely commits oneself, then Providence moves. too. All sorts of things occur to help one that would otherwise never have occurred. A whole stream of events issues from the decision, raising in one’s favor all manner of incidents and meetings and material assistance which no man would have believed would have come his way. Whatever you think you can do or believe you can do, begin it. Boldness has magic, grace, and power in it. Begin it now.”

#leadership #personaldevelopment #purpose #insight #innatewisdom #ceo