This week is Thanksgiving in the US. A time of reflection and gratitude.

And my good news for you this week may not feel good at first. But I assure you it’s the best news ever.

If you think you will reach a point in your life where you are finally satisfied, where you finally have and do everything you want, you are sadly mistaken.

Sixty years in, I am nowhere close to that space.

Yet I’m happier than ever. Many days, blissfully happy.

How?

Yes, I have gratitude. I take time to reflect on my relationships, my growing business, the impact that I am able to have on people’s lives, the meaning and purpose that I bring to my work.

But it is not those things that I am most grateful for. I am most grateful for the ongoing struggle. That struggle means I’m alive and growing.

Last year, I realized things were going pretty well in my business. I was working with clients I loved, I had more free time than ever, and my income was higher than it had ever been (setting aside the year my consulting firm went public and the year I got laid off and was paid out deferred benefits).

But I was listless. I was struggling to get through the day.

I was bored.

This is the other side of building a successful company, of building a successful career. It sneaks up on you and suddenly you feel depressed, because your work isn’t challenging, and guilty, because you are making way more than you ever thought you would.

So how did I get out of that?

I found a new challenge. Actually multiple challenges.

I created a group event for founders and am creating another one.

I created a tool, Pick Now, that helps everyone, not just the founders I coach one on one.

I started a podcast, The Pick Now Podcast, about the scary choices that successful entrepreneurs make over and over.

I’m speaking at events and building a keynote. I’m writing a book.

I’m simplifying my message and expanding my impact.

(And yes, I challenge myself physically and still practice tenor sax every day and love it.)

Every one of these is hard, and fun. I don’t know if they are going to work out. There is a very good chance my income will go down this year as I take these challenges on.

I would not give up those challenges for more income.

Because I am grateful for the struggle of being human. It is where I feel most alive, most “on purpose.”

And I bet the same is true for you.

Your Struggle is Built Into the System

For most of our existence, fat, happy, satisfied humans had one fate.

They were eaten.

Your ancestors were not. Your drive to continuously improve is built into your DNA. It’s what brought you here.

You think that dissatisfaction means something is wrong when actually it means the system is working perfectly.

There are two ways that you can deal with this. You can hide in the middle of the pack or you can lead it.

The Pack Is No Longer Safe

Hiding in the middle is safe but miserable. 95 percent of people get jobs, get comfortable, try their best not to take any risks, not to stand out. They strive to be useful and dependable and safe.

That worked for a long time. You could work at a factory and buy a house and get a pension. But then automation came. Then outsourcing came. Then AI came.

Hiding in the middle isn’t so safe any more.

Leadership Starts with Struggle

Your success is directly linked to how much you are willing to struggle. When I was laid off at 51, I was in the process of learning a whole new set of skills and I built a successful business from those skills. And I constantly challenge myself to do more, because I enjoy the challenge.

The times I struggle most is when I don’t have a challenge in front of me.

I hope to never be happy, because on the road to happiness is where I find the most happiness.

During this week of Thanksgiving I wish the very same for you.

This Isn’t Hustle Culture

I know this might sound like tech-bro 100 hour a week grind until you drop bullshit.

I assure you it’s not. This isn’t about grinding or productivity or inbox zero.

This is about taking on challenges that light you up.

This is about finally feeling alive again instead of constantly living in dread.

Keep Moving, Keep Growing

There is something you have been putting off. Maybe because it’s uncomfortable, maybe because you don’t know if it will succeed or if you can ever develop that skill.

In short, you keep putting it off because you’re scared.

But it keeps calling you. Not doing it is weighing you down. Avoiding it, avoiding that calling is exhausting you. And it’s time to take action.

I have a tool that can help. The Pick Now Decision Sprint can change your life in 30 days or less. And it’s totally free to my community.

Click on this link for access to the tool—

https://tinyurl.com/PickNowSprint

And let me know what you think.

Happy Thanksgiving.

#PickNow

I’ve now recorded twelve episodes of my new podcast, Pick Now.

I focus on the hard choices that founders make, over and over again, as they bring their visions into the world.

The things they struggled with, and the things they continue to struggle with, no matter their past level of success and what they are tackling next.

I’ve asked every one of my guests a version of this question—

“Do you think the entrepreneurial journey is a spiritual one?”

And every one of them has said yes.

The Questions You’re Trying to Answer

Every leader I work with has had significant success by the time they find me. But they might be exhausted. They might see that money isn’t giving them the happiness they thought it would. They might be finding they are always at work, even when they are with their spouse and kids. They might be worried about a health issue. And they wonder what all the hard work is all for.

Their questions are the same ones I continue to ask myself—

How do I stop being so hard on myself?

Why aren’t I happier?

What is my deeper purpose?

These are spiritual questions. And I find the more material success someone has, the more these questions lurk in the background.

Every leader has some version of this spiritual path, whether they call it spiritual or not.

This is mine.

Leadership is Learning to be Yourself

The first three decades of my life were largely performative. I got straight A’s in school, highest honors in college, degree from a top law school, partner track at a firm that was among the tops in the nation in my practice area.

And then in 1995, three months after my 30th birthday, I left.

At that point I would not have called my life spiritual in the least. But I was starting to see that the outer version of success didn’t feel all that fulfilling.

I was beginning to get curious. I had gone through phases, done some reading. Read the New Testament cover to cover during one semester in college, got curious about eastern philosophy during law school.

But my daytime, in the classroom and later in the office, was all about performance. About finding the next mountain to climb and then wondering why it only seemed to make my panic attacks worse.

What I Hid (Even From Myself)

I knew something was off. At the time, though, mental health was not talked about. I remember people in my family who beat their wives, who drank a six pack of beer every night and more. But it was the one who went to a “shrink” who was ridiculed.

So I told my wife when I started to meditate in 1996. But no one else.

I had buried so much. I had not let myself acknowledge all the things that I struggled with, in an attempt to “man up.” I suppose it was because any needs that I had in childhood brought up so much anxiety in my mom that it just wasn’t worth it. So I did my best, through positive thinking and self-medication, not to feel anything.

Or say anything about what I was feeling. (Not that I actually knew.)

I discovered, gradually and then suddenly, how unhappy I was in my carefully constructed life.

I left my marriage, I started going on meditation retreats, and working with spiritual teachers.

The Work at Work

And I started getting promoted at work.

I became a partner in the consulting firm I joined when I left the law firm. I managed a group of lawyers who were all at least ten years older than me. I managed large client relationships and moved from Chicago to Washington, DC. I led a team of national subject matter experts including some of the smartest lawyers, actuaries and pharmacists I had ever met.

I was showing up more. I was happier, more engaged, more calm. But I was still living two lives.

I wasn’t telling my work friends about my meditation retreats, and I wasn’t talking much about my corporate life when I was working with spiritual teachers.

Each half of me was embarrassed of the other, “weird” part. Until one day I outed myself to a spiritually curious friend. It got easier from there. But fully owning all the parts of me continues to be both difficult and incredibly fulfilling.

Finding Questions, Not Answers

We all have that work friend who has found (insert answer here) and is happy to tell you all about it.

I had a short period like that, too, where I thought I had an “answer.”

But as I studied more, as I practiced more, and as I coach more and more leaders, I have found that everyone has to find their own path. One of my early coaching mentors, Doug Silsbee, never stopped looking for ways to help people on their journeys, up until his untimely death in 2018. His “beginner’s mind” continues to inspire me.

What’s Your Path?

Most of my clients have specific “outer” goals. Revenue, profit, enterprise value. But they have seen what the traditional way takes out of them and are determined to do it differently.

Every leader I have worked with had a different version of that journey. A different version of those questions. A different way of challenging both their physiology and their psychology as they learn what works for them and what simply isn’t true.

What does that bring up for you?

For more, follow the Pick Now Podcast, subscribe to my email list, and of course follow me on LinkedIn.

And when you feel called, reach out directly.

#PickNow

I’ve never met a successful founder who wasn’t willing to make big decisions—while scared.

These founders aren’t impulsive. Or reckless. But they are willing to move on what they know to be true, even when they didn’t have all the data.

That’s what separates the ones who grow from the ones who stall.

You Already Know What to Do

I know that fear personally.

When I was laid off in 2016, I had every reason to play it safe—to get another corporate job, polish the résumé, wait for certainty. Instead, I took a leap into coaching (though I confess it took me a few months) with no guarantee it would work.

Looking back, that one decision changed everything. Not because I had it figured out, but because I finally stopped waiting to feel ready.

I knew that committing to coaching was the only way to get ready.

And as I began to work with founders, I saw that the more successful they were, the more willing they were to take action in uncertainty. To trust what they felt they knew. To react to what they learned from taking action. And to keep doing it until they got what they wanted.

That’s the essence of Pick Now—and it’s what my new podcast is about.

Learn From Others Who Pick Now

On The Pick Now Podcast, I’ll talk with founders who’ve made hard choices when the stakes were high and the outcome was unknown. Founders who sold their companies, walked away from safety, or built something new when everyone else told them not to.

They’ll share what it took to move forward in the middle of fear, and how those acts of courage reshaped their leadership, and their lives. Even when they didn’t work out.

Because fear isn’t a red flag. It’s a green light. It’s the last thing you feel before you take the leap.

Dropping Friday November 14

The Pick Now Podcast drops this Friday, November 14 wherever you get your podcasts.

The first two episodes are short solo episodes about my Pick Now tool and how the need to prove yourself gets in the way of creating anything of value. My in-depth interviews with founders start Friday, November 21.

Please make sure you subscribe and let everyone know about this ongoing conversation about courageous leadership.

If you’ve been circling a decision, waiting for “the right time,” this is the podcast for you.

Pick Now

Remember, clarity and relief don’t come before action. They come from action. Take action and see what shows up. Keep doing that and in a month you won’t recognize yourself. Do that for a year and your team, your board, your company will never be the same again.

#PickNow

I’m a big fan of the book 10x is Easier Than 2x by Dan Sullivan and Ben Hardy.

My favorite statement in the book is on page 69—

“[This founder] exhibits a quality that only the world’s top achievers do: the ability to rapidly accept a new identity.” — 10x Is Easier Than 2x: How World-Class Entrepreneurs Achieve More by Doing Less

There are two interesting things about this statement—

First, there is nothing in the rest of the book that explains how to do this.

Second, there is nothing in the rest of the book to suggest that entrepreneurs (or “top achievers” in the lingo of the book) are unique in this capacity.

Everything Comes From Your Identity

You’ve spent most of your life trying to figure out who you are—

Are you your achievements? Your job title or company name? Your relationships? Your history? Your sense of self-esteem?

All of these are concepts. Thoughts. They come and go with your moods, your physical state, and yes, the words you use to describe them. Even your stuff, the solid things that you have bought with money, are based on the concept of ownership. Another thought.

Every one of these things that we call “identity” happened in the past.

We talk of the “past” as solid and fixed but over the course of our lives we define and redefine its meaning over and over again.

Most of the time, most of us use the stories we tell about the past as a way to limit us. To keep us small and safe. And we change them only when absolutely necessary.

What if there’s another way?

How Have You Created Your Identity?

Most of us create our identity one hundred percent unconsciously, mostly in childhood, mostly by believing what authority figures have told us.

Once formed, we never touch it again.

You can see this, in yourself and others, every time someone uses a form of the word “is,” with or without the word “not” in front of it.

I am honest and hardworking. I’m not creative. That’s not who I am.

The rich are greedy and selfish. Life is hard. Nature is cruel.

Do you see that you’re not describing your reality with those words, but creating it?

How Tightly Do You Hold Onto Your World?

Even the most powerful leaders I coach, people who have grown companies worth hundreds of millions of dollars, will fight, sometimes for years, for their limitations.

One founder I work with continues to insist that only something outside of him (a sale of his company) will create “freedom” in his life. He hangs onto the pressure and stress he constantly puts on himself, terrified that if he stops, he will “lose his edge.”

He builds his prison quite willingly, moment by moment, insisting that it is useful, terrified to let it go in anything other than very small ways.

What Truth Are You Refusing to See?

Every step of the entrepreneurial journey requires a newer, bigger identity. Not one that takes on more, but one that lets go of more and more.

Until the very company whose success you poured your identity into now succeeds without any involvement from you whatsoever.

For most people, that level of success feels more like death. (I often hear of a valley of despair after successful founders sell.)

Are you willing to let go of your need to achieve and to get credit for that achievement?

Are you willing to?

A Faster Way to Learn New Skills

Most people learn new skills from their existing identity.

For example, an identity might learn the skills of “executive presence,” like a firm handshake or dominant body language or steady eye contact. Or communication skills, like reflective listening or nodding to show you have understood.

But anyone who had tried to learn skills this way knows how exhausting it is—

You have to not only maintain the identity that you have had your whole life, but you then have to learn the new skills through that identity. I have learned to be nervous and introverted and now have to paper over that with a firm handshake and eye contact.

The two are completely contradictory. Is it any wonder it doesn’t go well?

But when we stop trying to “be” something, we are actually presence itself. Those other skills emerge authentically and automatically.

They don’t have to be learned. They are innate.

Many of the other more holistic skills of leadership (connection, strategic thinking, emotional resonance) are also innate, if you can simply get your manufactured identity out of the way of them.

Who Will Challenge Your Limitations?

Most people are unwilling to see how their identity limits them, let alone challenge that identity. But identity can be changed and even dropped.

The first step is to see that identity can be developed, molded, changed. The next is to see that you can change in and out of identities as needed. Notice how you are different when you are at work, when you are with your partner, when you are with your kids or your childhood friends.

Notice who you are when you are at your childhood home over the holidays.

The final version of this is to see, to fundamentally realize, that your identity is 100 percent made up 100 percent of the time.

That you don’t even have to make up an identity to suit the occasion. You can just act.

And when someone else can see you and hold you to this, all the better.

The Easiest Way to Make a Dent in Your Identity is to Pick Now

Make one choice that is inconsistent with your current version of yourself. Something that you know you need to do that you have been putting off.

Take one small action, today.

What do you learn when you do this? What happens when you do it again?

Pick Now, over and over again, and your identity will change dramatically. You will see how unlimited you, your team, and your company actually are.

You will see your future possibilities differently because they will actually be different.

Want support on that? Reach out—I’m putting together something to help you change quickly and easily.

#PickNow