Founder Lost and Self Found
How letting go of what we were can make room for who we are
Welcome back to The Workaround. I’m Bob 👋
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Note: This is a longish, personal post that you might enjoy more if you hear me talk it through by clicking the play button above. Might be a good one to listen to while walking the dog, doing the dishes, or sitting on the deck…
Sometimes, the best way to find yourself is to get a little lost.
We can choose to let go of what’s comfortable, leave the map of expectations behind, and walk into the darkness—trusting that we can handle this.
“Travel…may reveal to the soul some image of that total perspective which is the ever-alluring mirage of philosophy.”—Will Durant, Fallen Leaves
Self-exploration mainly happens when we physically detach. It might be a solo hike for weeks in the woods. Retreat centers serve seekers in isolated locations where silence, prayer, or psychedelics can do their work. Whatever the destination, getting there is a conscious choice to let go of comforting surroundings and open up to something new within.
I’ve recently returned from such a trip. Traveling alone across six cities in two weeks, I found parts of me that had been hiding for 50 years. Among many revelations, I gained insights into what really, really drove me to become an entrepreneur, and why selling my startup hit me so hard.
It took joining the company of strangers in a strange land, ego naked and afraid, to uncover and encounter fears that were holding me back.
This post is going beyond my usual business stories. I’m taking a leap of faith that, by sharing who I am and how I’ve changed, I might inspire a few of you to uncover something new about yourself, too.
Preparing for Takeoff
It’s our 30th anniversary, and my wife, Steph, and I are spending a beautiful day doing four hours of yardwork together.
We’re back at our summer lake cabin, clearing a fence and trees that have been overrun with grape vines. It’s grueling work, and my arms are covered with scratches, but there’s something rewarding about working together like this. We even found some blackberry bushes that had been struggling to emerge. And the work has helped distract me from nervousness around my upcoming retreat.
In two days, I’d be heading to a form of spiritual retreat—the first-ever of any form for me. I’ve done plenty of travel around the world in my career, traveling to business meetings and conferences. But I left that game to focus on personal growth. It’s not a mid-life crisis…maybe a mid-life re-evaluation.
Two years ago, I joined a “wisdom group” of 150 similarly seeking peers called Leading Edge. Through this group, an opportunity arose to travel to Glastonbury, UK, for a weekend retreat with a philosopher and spiritual writer named Tim Freke.
I didn’t know what to expect, and I only knew one other participant in the session well. I felt far behind on the spiritual seeker scale, with no workplace accomplishments to help me establish credibility and protect my ego here. But I still felt compelled to make the leap and sign up for this event.
In the meantime, I was invited to join a small group of mostly professional public equity investors in Croatia. It was another event where I only knew a few people and was an industry outsider. But I trusted our host would put on a wonderful event, and I committed to this as well.
With only a week between the two trips, Steph encouraged me to just stay in Europe instead of wasting two more days and a plane ticket on back-and-forth from the U.S. It sounded smart, and I thought I could keep myself busy, so I arranged travel for over two weeks on my own.
Keeping Glastonbury Wyrd
Two days later, I’m sitting in a circle of chairs in the retreat room, wondering what I’m going to say when it’s my turn to answer the question: “What do you wish to get out of this experience?”
My mind went through its usual new-group strategies—and worries: First impressions are key. Try to sound smart. Don’t embarrass yourself. Probably better just build on what others say…
Two people before me, a woman wept as she shared details on the clarity she sought. I think her open, honest expression made me feel safe enough to share what was really on my mind. And this is why I came, right? So I abandoned my comfort zone and shared what was really on my mind:
“I had episodes of very poor sleep in the couple of weeks leading up to this event. This is very unusual for me. I wasn’t consciously feeling the stress and worry about this or anything else in my life. But once again, I found myself wide awake at 2 am. I read a book for a while, then closed my eyes to try to drift off.
“Suddenly, I ‘heard’ a voice from my mind start to form words. It wasn’t the usual ‘thoughts voice’ that reminds and warns me all day. This voice seemed to come from a different region, and instead of suggesting things, it was crying out like a child: ‘I want to play. Why don’t they want to play? Do they not like me? Why won’t they play with me? It’s so fun. We’re here for play.’
“I was reminded of what ‘play’ meant to me as a child. Playing soccer or touch football with friends, a time before forming identities and joining cliques, worrying about grades, or what we’d do when we grew up. That perfect time in childhood when nobody’s judging. You’re just in the moment—present, alive, flowing…riding the bike of life without over-thinking what keeps it from falling down. That precious time when it didn’t matter what you looked like, what you were doing, who you were, and whether you were good at the game or not. You’re just in the moment, playing as one team.
This is what I want in life now, and what I’m hoping for in this retreat.”
Whew! I got that out, and didn’t melt down. But I was on the verge of tears as I expressed this to the group. Then we moved on to the person on my left.
With this circle of trust established, the following 48 hours were a blur of group bonding and self-discoveries. Through retreat sessions, long meals, and exploring Glastonbury’s mystic surroundings in small and large groups, I felt layers of social defense screens melt off me. With these weights lifted, I felt more alive.
A highlight was when a smaller group of us hired a driver to take us to the ancient Avebury stones—a collection of Neolithic monuments older than Stonehenge, scattered among fields of gold. We frolicked among them as the sun set. I found my heart full of love for these new friends and this ancient place.
My head hit the pillow around midnight, and as I closed my eyes, I saw a series of images in my mind. I’d never experienced something like this before. They were high-definition photos of vines climbing up and around various fences—from old stone walls to tennis court chain links.
I thought about a vine analogy that has come to mind often in my past few years of self-work. I’ve felt my Ego—in the form of fears, attachments, projections, and identities—is like that grape vine continuing to crawl up my legs and hold me in place. Each time I take a new step, the Ego vines try to hold me in place again, and I have to hack myself free.
But these images felt like vines spreading out from me. Instead of holding me in place, they seek to connect with others. These past few days showed me that a deeper connection was possible.
The Medium and the Message
But my Glastonbury experience was far from over.
The next day, another small group of us spent an afternoon with a highly attuned spiritual person. Some might call him a Medium or a Clairvoyant. Whatever the title, signing up for this experience was something I couldn’t have imagined a few years ago, when I was full of doubt and skepticism.
But now, I saw this invitation as a life experience to be entered with curiosity and openness. There was no reason to fear, and I chose to go in with a willing suspension of disbelief. It’s the same way we read a book or watch a movie, allowing ourselves to relax and absorb the story and its meaning. Relaxing assumptions means our ego defenses come down and we can look at ourselves in a more open, fresh way—without losing discernment or signing up for a cult.
For me, personal experiences with astrology, tarot cards, psychedelics, dream analysis, past-life regression, and other “woo” topics can provide a mirror that lets me see myself from a different perspective. Our unconscious has vast intelligence and wants to communicate with us, and by stepping outside a purely rational, materialist mindset, there is space to discover more within. If something in these experiences grabs your attention, it is the psyche trying to show something through symbolism—the main language it speaks. You don’t have to buy into a new lifestyle; it’s about seeing what resonates with you and then wondering why.
Look, modern society is coming to agree that the body knows the score. Noticing how mental stress activates our breathing and pain receptors is now accepted. But this stuff was labeled Woo, too, just a few years ago.
The next step is mining what our unconscious, or the psyche, knows. Generally, the psyche wants us to grow, flourish, and find a higher baseline of peace and creativity. It knows where the internal bodies are buried—the traumas and bad habits holding us back. But our ego and all of its defenses, projections, attachments, and related fears get in the way of this growth. Turning down the ego's voices by relaxing beliefs allows helpful messages from the psyche to arise. Then we can consciously consider such messages and sometimes rewrite our own programs to improve them.
Your mind “must be like a parachute, which is no good unless it opens up.”—Joseph Murphy, The Power of Your Subconscious Mind.
Back to Glastonbury…In a small room in our rented Airbnb, our Medium guide led us through a multi-hour group meditation. Along the way, he pointed out parts of ourselves that were both unfolding and holding us back. One of the specific things he saw in me was that “I don’t have to pick up the pieces of my broken statue (identity) and can fully go into my new life.” His words resonated with my uncovering of social fears that held me back for so long.
After another sleepless night filled with electric visions and dreams, our group gathered with him the next morning for a debriefing session. I felt like I had been wrenched open with a crowbar. And it felt really good.
Before tidying up to leave the rental house, Isik from our group pulled out a handful of painted stones she bought in town and told us each to pick one. My hand jumped to one with a honeybee, which fit with one of my crazy dreams the night before. She pointed out words on the other side: “Be Yourself.”
Then Jeff suggested a group hug. We came together and intertwined our arms tightly. Ali said his favorite prayer. Being the tallest, I had a view of the entire group. I noticed that our arms were like intertwined vines…so beautiful. No one wanted to break the embrace.
Eating Alone
The next day, I spent several hours on trains to Strasbourg, the first stop in my solo journey to my next event in Croatia. I had picked out this city on the French-German border because it was on the way and a place I had not visited before.
For me, France is about wonderful food, and it doesn’t get more wonderful than a multi-course meal at a Michelin-rated restaurant. So I reserved a spot for one at a place just a short walk from my hotel through the old town.
The message from the restaurant said that they would seat me at a bar in front of the kitchen, which I figured would be something neat to watch since I was eating alone. But when I arrived, they sat me in a charming room with an empty seat in front of me:
After days of intense, loving, wonderful human contact, here I was sitting alone. The surroundings and food were way too nice to pollute with a phone in my hand, so I decided to turn this 3.5-hour meal into a kind of silent meditation. The wine pairings helped.
Between bites, I imagined many people in the chair in front of me. My family members and countless people I’ve known over the course of my life—some still with us and others gone.
I continued a series of very long walks, museum visits, and meals alone from Strasbourg to Munich to Vienna. Often, I asked myself: Why am I feeling so raw? What’s happening to me?
After selling my company, failing at another one, and finally doing some self-work, I had let go of my identity as a Founder, CEO, Business Leader, Marketing Strategist, and more. And now, as I forced myself into situations where those identities could not serve as armor to protect me, I saw the layer of social anxiety lying underneath.
I was naturally introverted as a child, often hiding behind my mother’s legs when around strangers. And across my formative years, I moved schools several times. I was on the smart/nerd side, which put me on the defensive. Each new school situation forced me to create strategies for fitting in, often by hiding my true self and adapting to others.
Most people I’ve met would probably be surprised to read that I’ve got all kinds of social anxiety second-guessing going on in my mind. As we spoke, countless voices barged into my brain: Am I talking too much? Did I just overshare? Are they looking at the clock? Did I tip enough? Is there something in my nose?
Oh, and nearly every morning in the shower, thoughts arose about whether I said something yesterday that offended someone.
I know how these voices formed in me, because I’ve seen the process happen with my children, too. There was that time when my kids’ school had a Daddy-Daughter dance. My younger girl was the life of the party, begging to dance again and again with a giant smile on her face. So I signed us up when the dance rolled around the next year. But this time, I could barely drag her onto the dance floor. Her self-consciousness kicked in, and my heart broke.1
This happens for most of us as our egos form and social pressures take hold. Then it can take a lifetime to hack that away. Most never will.
As I unwound my memories, I realized that one reason I became an entrepreneur was to make friends and reduce my social anxieties! Employees become an automatic friend group. And this is why selling my companies hit so hard. I lost contact with my tribe and had to start something up all over again.
Leadership itself brings additional social pressures. To succeed, you have to become so much more attuned to others: Are they engaged? Am I giving and getting eye contact when speaking? Am I behaving in a way that encourages or discourages them from trusting me?
I saw this in other coaches and therapists who attended our retreat. They spend so much effort holding space for others that they have trouble drawing a line between others and self. Most therapists see their own therapists.
Forcing myself into that retreat allowed me to see how fully dropping social fears can bring me closer to other people—to make new friends instantly and see strangers in an automatically positive light. And to enjoy the presence of others even deeper, while allowing what’s best in me to shine on them.
Now, by letting that go, I had an amazing experience. This is how it can be in my life! I don’t have to be afraid of people anymore! I can PLAY again! Then tears, too, as I realized this is how I could have been all along. Oh, how many opportunities for deep connection did I miss? But now, I know.
Jumping Into Practice
I arrived in Dubrovnik eager—maybe desperate—to connect with people again, but it was still hours before our kick-off. I walked around the cliffside hotel and saw teenagers jumping off the cliff into the deep waters below. I hadn’t jumped off a cliff since my first trip to Europe in 1994, when backpacking with friends in Greece—not too far down this same coast. I knew I’d have to do it again here before I left.
Then, another small group of strangers and another intro session. This time, we were split into one-on-ones to share our stories. I decided to go with the cliff metaphor and be myself, even if it might be shocking to the other person and uncomfortable to me.
I shared a brief overview of my spiritual retreat in Glastonbury. My partner replied that he also went there for meditation retreats about once per quarter. From there, I was off to the races…
Over the course of the three-day event, I kept opening up, cutting through the small talk, and having deep conversations with people eager to share. Perhaps the highlight—and far from unique—was hearing a straight-laced looking 45-year-old manager of billions of dollars in capital describe his participation in weekly meditative dancing classes.
Maybe everybody’s got something they’re trying to figure out and are afraid to share with each other because of the social limits that hold us back. But once again, by putting myself out there, I’m seeing more of them. They’re seeing more of me, and we’re coming out so much better at the end of even a 15-minute conversation.
It was at this event that I realized the best way to open ourselves up is to take action. We can’t beat the thoughts in our heads into submission by using more words against them. When leading ourselves, our system watches what we do, not what we say.
Throwing myself into these challenging situations shows the ego and psyche who’s boss. And on the other side of action, we get real-world information. The fears are proven unfounded. Excitement rises. We learn new lessons. We gain confidence, and our nervous system is more relaxed the next time we take a risk.
And as the last day of my journey abroad dawned, I knew it was time to throw myself off the actual cliff. After a 6 am yoga session, I walked over to the spot those teenagers had been daring each other to launch from. I stood there for a moment, looking down and somewhat worried about picking the deepest spot.
Then I caught movement on my left and saw Priscella from our group holding her phone and motioning me to jump off. So I leaped off with “Woooo!” that must have woken half the hotel. And as I rose to the surface, I felt so much baggage dissolving. I floated, without effort, and wondered if the rest of my life could feel like this now.
Bringing it Back Home
I never knew how much a retreat or solo travel could change a person—especially me.
They say we’re in a “loneliness epidemic,” but maybe a bunch of us have shit to figure out. For thousands of years, men and women have taken time away from others to sort things out for themselves.
"All of humanity's problems stem from man's inability to sit quietly in a room alone."—Blaise Pascal, 1654
My friend, Meghan, from our retreat, wrote about her “Joy Trips,” in which she takes an annual solo break from the real world and all of its work and family responsibilities.2 Sadly, most people she meets can’t imagine doing something similar, yet more social “rules” that keep us stuck in place.
I keep running into other examples of people whose solo journeys lead them to connect deeper with others…
Douglas Rushkoff, a middle-aged guy, shared something similar in his recent post about a retreat with a group of people he didn’t know. For him, the words of another 17th-century philosopher, Spinoza, came to mind:
“The very definition of a person’s power and vitality—their life—is their capacity to affect and be affected by others.”
I also enjoyed Heather Havrilesky’s story of finally learning in mid-life that:
“To grow in this life, you have to know things you don’t want to know. You have to learn things you don’t want to learn. You have to open your eyes to your greatest fears and your deepest wells of sadness. This is where maturity comes from! You blossom into a full, balanced, happy adult when you dare to reckon with yourself as an organism among other organisms, and you dare to attune yourself to how you feel inside and how the world feels around you.”
Travel gets us out of our comfort zones, helping us open up to new information.
But these Trips don’t count unless we integrate them into our everyday lives back in the real world…
I noticed immediate differences upon my return. I started leaning into conversations with strangers on the street, while waiting in lines, and with the guy in the barber chair next to mine. I found myself looking in the eyes of friends and strangers more, and just genuinely happy whenever I meet, well, just about anybody.
I increasingly see each person as holding treasure just below the surface. Sometimes literally.
My prior fears, second-guessing, and judging seem dissolved. I keep asking myself, “Who is this guy?!”
And my time away gave my wife a chance to do some soul-searching, too. Upon my return, we traded journal entries about what we discovered. With more internal barriers dissolved, we shared things we had never shared in 30 years of loving marriage. I never thought our relationship could go further in another couple of decades, much less two weeks. Wow.
Find Your Gold
It took me a few years to stop being stuck playing a role. This trip helped me stop being afraid to be seen without one.
I’m being myself more than ever in my life—and in this process, I’m feeling more connected to everyone I meet. Maybe this is what Oneness is about…?
But this is just my path. Yours will be different because we are all unique. My humble suggestion is that a beautiful part of who you are lies beneath the surface, covered by defenses against perceived dangers in the outside world.
Follow that still small voice of growth that wants to emerge. Take some action on your own to explore who that is. Notice how you feel. That’s You, waiting to crack out of the chrysalis and fly. Waiting for you to Be Yourself.
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My daughters have made a lot more progress in their 20s than I have in my 50s. Maybe because of the peer group, or maybe it’s the generation they’ve been born into. The latter gives me lots of hope.
I’m the “Bob” in her post.
I enjoyed every minute of this Bob! So authentic - and how cool to be on this journey together 🙌
Ughhh, this post is SO beautiful! The part about the vines that had grown to hold you back now being ones that were reaching out to others was so visceral and lovely. I couldn't be happier to know you and have been a small part of this particular journey.