(Now you just need to do it.)

It’s February.

Remember that list of things you were going to take on this year? The new hire, the firing of that person who just wasn’t right for where the company is? The new investor, the new board member?

How’s it going?

If you’re like me (and like a lot of my clients), you resist big decisions, thinking you can figure out exactly how they are going to work out before you make them.

I have bad news for you.

There is No Fork in the Road

So many of the founders that I work with create a narrative that looks something like this—

There is a critical decision to make. There is a “right” path and a “wrong” path. If I study the data enough I can figure out which way to do.

I can figure out the result in advance.

There are two problems with this approach—

You will never think you have enough data, and—

More importantly, there is no “right” path. There is no path at all.

If you think you are following a path, chances are you’re not doing anything very original (or “ground-breaking,” another made-up concept). You’re just doing the same thing that someone else did.

The only path is to try things, see how they work, and adjust. Over and over again.

This is the “path,” and it is deceptively easy until you try it. Which is why the willingness to be a founder, to do something “ground-breaking,” is rare in our culture.

For most people, the fear and uncertainly is just too great.

How do you know what to do?

Notice the Quiet Knowing

Ever hear that voice that says “I knew I should have…”?

How would your life be different if you started following it more? Even if it’s unreasonable? Even if it’s a bit uncomfortable?

That knowing, that sense, came uniquely to you. It is your gift, and it will show up for you just a little bit different than anyone else.

I have said “Desire is a gift from God.” Whether or not those words resonate for you, the truth is that you made every major decision with your gut. I have never met a person who picked their spouse based on a spreadsheet.

You won’t make major business decisions that way, either.

Learn by Taking Action—Quickly

You won’t figure out anything without taking action, and the faster you figure this out the better you will do.

In the startup world, people urge you to “fail fast.”

If that feels too rash, take action when you are about 80 percent certain. And then see what happens and figure out what to do next.

The big secret in all of this is that you will make much faster progress failing over and over than you could ever make trying to succeed the first time.

Thoughts on this?

Drop a comment below.

I had my second saxophone performance on Sunday. My last one was in May of 2024 after about 11 months of learning the alto sax.

So much has happened since then. I switched from alto to tenor. I moved from a group that was focused on rock to one focused on jazz (and jazz improv). I have come a LONG ways—better at playing in tune, being able to actually improvise at a rudimentary level, getting comfortable with changing instruments and mouthpieces and reeds.

But my FIRST reaction when I watched my wife’s video from my performance was feeling self-conscious about how awful I sounded.

Seeing Potential Rather Than Accomplishment

In every regard, I am a dramatically better sax player than I was last May. But my focus was on what I was NOT doing well, rather than how I had gotten better. Coach Dan Sullivan calls this perspective “The Gap Versus the Gain.” The idea is that we always evaluate ourselves against our potential rather than seeing how far we’ve come.

It’s a very human thing. It also keeps us mired in dissatisfaction.

Is it helpful? Absolutely. Because there is always more to do, and to be, and let’s face it, dissatisfaction is motivating, if exhausting.

But no matter where you are, you are just getting started AND you have already come so far.

The trick is in being able to hold both. To be grateful AND inspired.

Having Help Along the Way

I have a great teacher who has been with me from the start. He has an academy for kids (six bands of kids performed Sunday after we did, and they were AWESOME). And with me and a few others, he is beginning to teach adults who are new to their instruments.

One of my favorite things about him is that he doesn’t get too worried about how much more I have to learn. (Like I do.)

He only focuses on the next step. And then the next step after that.

Sometimes I get impatient with that. I get frustrated with myself, with him, with the fact that things aren’t going faster. But every time I get ahead of myself I find it only slows me down.

Who in your life reminds you how far you’ve come? Who in your life keeps you focused on the very next step when you could easily get overwhelmed by everything there is to do?

There Are No Shortcuts

The internet is full of overnight successes who have been at it for ten years or more. (I’m in year nine of my coaching business—I know.)

It can look like someone suddenly made it big, but if you look closely, you will find that’s never the case.

I didn’t start playing saxophone at 58 because I thought I would get good fast (though I did HOPE that, I confess). I started for two other reasons—

First, I love jazz (think Miles Davis Kind of Blue era stuff) and had always been fascinated with the idea playing an instrument and being able to improvise on that instrument. I have literally had dreams of playing the sax, and when my son quit in eighth grade I suddenly had both a saxophone and a teacher readily available.

Second, I know my 78-year-old self will appreciate having twenty years of saxophone experience and I really want to give him that gift.

What’s the Gift You Want to Give Your Future Self?

What would your future self most like from you?

What could you do today to start to give that?

What regret will you have if you don’t?

They say that you shouldn’t die with your song still unsung. What does reading that bring up in you?

Drop a comment below with your thoughts.

I reached out to a founder I know a few days ago, just to check in, to see if 2025 was off to a good start. I was doing this with a few people, and just wanted to get a couple emails out there before I went off to do other things.

I wasn’t thinking.

This founder lives in LA. Santa Monica, to be precise.

Close enough, it turns out, to have been evacuated twice because of the fires.

🤦

In my rush to reach out, I was making it about my agenda, about what I wanted.

And while he was gracious about it, I can only imagine how he felt.

Is There an Agenda Behind Your Caring?

I always want to get off to a good start in the New Year. It’s often my busiest time of year. Founders come to be because they went through something that they don’t want to go through again, whether it’s getting stuck, not trusting their people, being exhausted, or all three.

At times I notice an urgency to that. There is some FOMO, that if I don’t capitalize on the first part of the year the rest of the year is doomed to fail.

And that focus on myself, on my agenda, can lead me to do some stupid selfish things, like sending an email to someone in LA with the subject line, “Is your 2025 off to a good start?”

I hope I’m learning from this. Because your agenda can show up in so many ways—

When you are talking with a potential client.

When you are talking with an employee.

When you are talking with a potential investor or board member.

Do you want a relationship, or just transactions?

The Presence of Authentic Relationship

One of the things that I constantly strive to get better at sounds deceptively simple—

To slow down enough to be with the person I am with.

Whether that’s my client or my spouse, can I be there for them, and their agenda?

Can I set aside all the other things that I am thinking about, just for now?

Can I repair when, inevitably, I DON’T do that?

Does This Resonate?

If so, reach out. I would love to hear how this shows up for you.

I’m creating my next Zoom call for founders and would love to hear what is on your mind. What YOU are struggling with and who you’d like to hear from on that topic.

And I’m creating a special two day event in Denver this coming October, on The Art and Science of Next Level Living. A small group of founders looking at big questions—

Is this (a financially successful business or exit) all there is?

Why am I ACTUALLY here?

What’s next for me?

Let me know if you would like to be considered for either or both of these events.

Last week, when I wrote about creating in 2025, there were a couple of lines I added that at the time felt like a throwaway—

When you get out of the way, it might feel like something is calling you to be created. Or that something is wanting to emerge through you. Honor that.

What if this is actually the highest form of creating?

I realized that I could have and should have said more—much more—about these two lines.

That a newsletter was calling to emerge just on this.

It’s a path I’m familiar with.

You, on Purpose

There are a lot of ways to create in the world.

Yes, you can create something to make money, whether a profession, a career, or a business.

Yes, you can create something because it brings you joy—simply because it is fun to create it.

These ways of creating might feel a bit difficult at first, but they get easier. And more fun.

But they aren’t always the path to fulfillment.

Sometimes, it feels like life is calling on you to create something that you don’t want to do. That you resist doing. That feels too big or scary. That you have no idea how you could possibly do it.

In August 2016 this happened to me. And as I face my 60th birthday, a bit less than a month from now, I want to share more about that journey. I want to share why I’m so happy that I trusted my instincts and, at least after some initial resistance, took the leap.

And I want to suggest that something might be calling you, too, if you get quiet enough to hear it.

A Calling or a Fantasy?

I’ve been on a self-improvement journey in one form or another since at least the 1980s. I began a decades-long meditation practice in 1996. I started going on retreats and working with spiritual teachers in 2005. But I didn’t discover coaching as an occupation until 2008.

I didn’t seriously consider it as a potential occupation for me until about 2014. Though I did tinker with trying to get some clients on this side along the way.

Even when I was laid off from my last corporate role in 2016, it never occurred to me that I could match my prior salary working as a coach.

It seemed totally impractical, a pipe dream.

But it’s happened.

Because even though it was frustrating and difficult, there was something in me that was determined to make it work.

To reeducate a network of people who thought of me as a lawyer and consultant and health care expert.

To retrain myself on working on the self (both mine and others), something ultimately impossible to understand, rather than the skills and strategies and content that I did know.

To slowly build a business that has grown every year and that now well exceeds my prior salary.

When I started I had never had a paying coaching client, let alone worked with a founder. Today, founders and CEOs pay me six figures to work with me.

How does this happen?

The Most Powerful Commitment

One of my coaches along the way, John Patrick Morgan, said something that continues to inspire me—

“The most powerful commitments are the ones that you have no idea how to fulfill.”

My experience has taught me something even more compelling—

If you really want to create something, the universe, which somehow planted that seed in you, will also guide you in how to create it.

You can call it whatever you want. Whatever works for you. Your gut, intuition, guidance, angels, God.

But there is something that, when we get out of the way, shows up to help us.

Within your desire is hidden the means to achieve it.

For the first several months of my new coaching venture, I thought I was committed. But I am now convinced that one other thing was necessary for that commitment to be absolute.

Burning the Bridges

When I was working in the corporate world, I was living in Chicago and then later Washington DC. And I commuted to Boston for about six years, too.

Big cites with lots of traditional employment opportunities. And lots of fallback options when I was initially thinking about coaching from 2010 to 2012.

Those options were keeping me from fully committing to coaching.

One of those options turned into my last corporate job.

But things changed when we moved from Washington DC to Carbondale CO, a small mountain town near Aspen, in July of 2017.

There are no positions here that are anything like what I had access to in my old world.

Suddenly, the fallback was gone. And it was the best thing that ever happened to me.

A Willingness to Be Curious and Change Course

When I first got laid off, I thought I’d be a consultant.

Maybe I could coach part time, a good friend suggested, while building a consulting business.

I was known as a health care expert. I was confident that I could make it work there while I built my coaching chops.

But no one wanted to hire me as a consultant.

Even though I did get some interest from potential employers, I didn’t pursue them. I knew deep in my bones that my next thing was on my own.

I attended a coaching intensive a month after getting laid off. I hired my first coach, Rich Litvin, a few months after that. I did a lot of things differently than others were, because they felt right to me. I never coached for an hourly fee, instead waiting for more substantial engagements.

My first client was a senior executive who hired me in June of 2017. With some breaks, we worked together four years.

My first founder was a referral in late 2018 and we worked till the middle of 2023.

My second came shortly after and we worked through the sale of his company.

Even though I have coached some great senior executives along the way, there was something about founders, about their capacity to look deeply at themselves, to take risks, and to apply themselves over a period of years, that resonated with me.

Perhaps because, looking back, that has been my path, too.

I’ve moved from coaching executives to coaching founders to coaching second time founders to coaching people who have had exits and are wondering what is next. Not by design, but simply because that is where the path seems to have led me and that has been my clients journey, too.

I never planned any of it. (In fact, a lot of the stuff I thought would work failed miserably. That’s a whole different newsletter.)

What is Calling You?

As you look at a new year, maybe there has been something that has been calling you. With a quiet, but insistent voice that, to this point, you’ve been ignoring.

Maybe you tell it “someday,” or, “it’s just not practical right now” or, “it’s too risky.“ Maybe you ask yourself, “Who am I to think I could do that?”

Every day that passes without taking action, a little part of you dies.

Maybe you want to pursue a different career or start a business.

Maybe you’re already running a business, but you can’t quite seem create the next version even though the thrill is gone with this one.

Maybe you’ve sold a business and have no idea what is next for you.

Get quiet. Give yourself some space. And see what emerges.

Continuing the Conversation

One of the things I’m creating in 2025 is more opportunities for both individuals and small groups to spend time in that space where dreams emerge.

Watch this newsletter for more, and reach out in the meantime if you’d like to talk.

I’m creating a special email list just for this project and would love to include you.