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