Welcome back to The Workaround. I’m Bob 👋
You’re in good company with over 11,000 fellow entrepreneurs and innovators who follow my stories from a career in tech startups and corporate innovation.
I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.
Listen by hitting the play button above or using your favorite podcast app. Or listen and watch on YouTube.
Instead of looking to climb the next mountain, we may be ready to flow with the river.
“Don’t do anything for at least a year.”
This is the most common advice that post-exit entrepreneurs share when they write their books or appear as guests on podcasts. They caution that there is a natural tendency to want to get back on the horse, to build something bigger and better, and keep the dream team working together.
It’s the advice I give, too. The only problem? I didn’t follow it when I should have.
It took me four years of grinding through the challenges of building that next startup. Finally, with the help of friends and getting smacked in the face by reality, I escaped the role I rushed into and found a better path forward.
And it took me a few years later to finally understand why I didn’t listen to this chorus of advice. This is my story, which might help you learn the lesson faster than I did.
Most people on the other side of a big self-discovery say that it took a crisis to get them there. It’s that point where the ego hits its limits, burns down, and makes room for a new and improved Self to form.
But every path is a little bit different. Any progress I’ve made started with a mini midlife crisis that I think I’ve had every day of my life since my mid-20s. In other words, I constantly reflect on how I got to this point in my life and whether or not I’m on the right path.
But I did have a moderate breakdown in Fall 2019 that helped me build back up.
It happened during the second and final year of an earnout as part of the sale of my startup. I should have been ecstatic; we secured a great deal for the company, our team was well ahead of pace in maximizing the earnout, and our new owners essentially left us alone.
The problem was that I could see that the good times wouldn’t last much longer.
I spent much of my days working with the leadership team of our new acquirers—mostly playing defense so that my team could remain left alone. It was not a pleasant experience. No one was evil, but they were wrapped up in the kinds of politics and power trips that I had left behind long ago. I knew that our wonderful culture and high-performance team would be swallowed up in this awfulness eventually.
The hardest part was having new bosses in my head.
We live in social cooperation, so our minds form models of our friends, family, co-workers, and clients. As CEO, I didn’t have a direct boss to occupy my mind, so I could focus on my team. And since we built a very strong culture with positive relationships, my mind was full of love and positivity. Each day felt like a peak experience—like a Heaven on Earth.
But now this peace was invaded by people who worked in a culture led by a CEO who cared little for others. It was his way or the highway, and his way was adopted, in turn, by most of the executive team around him. They were in a kind of Hell that I had freed myself of long ago.
Coming to work each day was quietly miserable. I was mostly smiles on the outside, as I knew my teammates’ eyes were on me. But inside my heart was breaking, and my blood was boiling. My doctor flagged high blood pressure for the first time in my annual physical.
As the months progressed, it became increasingly difficult to control my reactions. I got snippy in emails. I lampooned the acquirer on our team’s Slack channels. I disrupted meetings by calling out bullshit.
I realized that I might go too far and sabotage our efforts.
So, in October 2019, I decided to take a break. I abruptly told my boss I was leaving for a week-long vacation. I had no idea where I was going or what I was going to do. I just needed to escape.
After strategizing with my wife that evening, I decided to put the dog in the car and drive to a rental home in northern Michigan, an area of the country we had spent many pleasant summer vacations.
I packed a bunch of philosophy books and some thoughts I had jotted down over the previous few months. It wasn’t too far from what Jack Nicholson wrote to himself in The Shining.
Over that glorious week in the dark, frigid Fall, I explored that feeling of others in my mind. And somewhere between reading the words of Robert Greene and Eckhart Tolle, I landed on an epiphany: I get to change my mind.
My negative emotions and thoughts were something I had the power to control. I was not a victim—I was allowing an unexamined part of me to run the show. I could model people without letting them run loose in my mind. I could take responsibility for everything and shift it all to a more positive frame.
I spent my final few days of solitude crystallizing key insights and suggestions from Stoicism, Buddhism, and Christianity. I applied my strategic thinking skills to compose a personal one-pager on how to operate going forward. And I came up with a guiding principle: I would use my remaining few months embedded in the negative culture of this acquirer to test and better myself—I would come away with life lessons worth much more than the check I would get at the end of the earnout.
Then I drove back and quickly dove into this self-work.
I began each day at the office meditating in our tiny, windowless Mother’s Room. I became more aware of my thoughts and emotions rising, and I practiced patting them on the head and letting them go. I laughed at myself when seeing negative reactions rise at annoying meetings or emails.
I recall a particular test when sitting in an all-day leadership meeting, listening to the CEO announce a completely ill-thought-out company strategy, followed by his presentation of New & Improved Company Values, which he bragged took only 90 minutes of discussion. I sat, smiling blankly, refusing to get worked up. My friend across the room, Jeff, later marveled at my Zen-like stare through it all. Inside, I was more like Homer Simpson trying not to fill the swear jar.
The efforts helped me at work—and beyond. I surprised myself by laughing when cut off in traffic. It’s hard to communicate how big that little change was! And noticing my mind’s changes became encouraging fuel to go further. It’s working! I’m reprogramming my own mind!
Then something else amazing happened: two of my friends (and fellow exec team members) and I discussed teaming up again.
We each saw that this company was not a fit, and we loved working together. Why not start up again? My heart raced at the idea of plunging into another challenge, armed with some money in the bank, trusted co-founders, and the chance to do something more meaningful with fewer unforced errors this time.
The three of us began to meet after hours in a separate co-working space, where we would spitball ideas and share research on new industries. While we met sparingly, most of my waking thoughts were about the possibilities of what we could do next.
We could build an even better company. We’d raise less money, form a strong culture earlier, hire known talent, and make a bigger positive dent in the universe.
But this is where I made the mistake that so many other founders warned of…
I stopped thinking about how to build a new me first. Looking back, I think I was afraid of what I would become without a team, a cause, a next big mountain to throw myself against.
Like many driven entrepreneurs who throw their entire heart and soul into their companies, I had completely identified with my role. The business was my baby; it was an extension of me. It was a product of my personal development toward that of a more enlightened leader. But as the earnout clock ticked closer to the end, I could unconsciously sense the pending loss of a core part of my identity.
If I wasn’t a founder, who was I? It was easier on my ego to jump back into the battle.
Time moved quickly. We got our checks. I got myself fired. COVID hit, and scheduled virtual meetings with potential clients and investors for the startup idea we eventually landed on.
But we didn’t make that big dent in the universe. We pivoted from B2B HR SaaS, to a professional social network, to a Web 3.0 concept, and finally to a recruiting service—the toughest job I never loved. Each was a fresh crawl through glass to get from zero to one.
As the years passed and our company failed to progress, my small team and I eventually saw the writing on the wall. I think we would have quit earlier except that we had so much fun spending time together.
But eventually, we accepted it was time to move on. After five pivots in four years, it was time to take the “L.” Writing my first note of failure to our investors, which included some close friends who were excited to back us, wasn’t fun. I had never given up on my own business before.
I was back to ground zero, with time on my hands.
Thankfully, that old personal development playbook was still in the back of my mind. I picked up a meditation habit again. I wrote in my journal. I spent more time alone and with fellow seekers. I got serious about using this Substack as a tool for reflecting on my work+life experiences, as well as helping others on their journeys.
And I felt progress stirring inside me again. I “exceeded KPIs” in measures such as higher happiness, lower intolerance, and greater awareness of the beautiful little things in life—including each person I get to spend time with.
I became grateful that the next startup didn’t work out, as I’d be back in the same place as a person. Its failure became a gift in helping me find a higher level in the game of life.
Then the universe delivered us the chance to restart our old, successful startup. Our acquiring company was sold, and our remaining team was laid off as part of the PE buyer’s cost-cutting strategy. But the product was still in high demand, and customers were eager to keep buying. My partners and I decided to invest in putting the band back together. But this time, we took a back seat as investors and coaches.
By making room in my mind and letting the universe present opportunities, I was able to see a new path forward. Today, we’re enabling others’ success, and we’re doing it without raising a fund or pressuring ourselves or our CEOs to blitzscale.
My new job doesn’t occupy 40 hours per week, so I’m spending the balance of time on further self-understanding and improvement.
It’s work that’s not rushed. I’m not into intense retreats or finding a guru. Instead, I spend most of my time reading, writing, and trading ideas with a community of fellow seekers. Each of us is finding our own path rather than following a leader.
And I increasingly turn every business meeting, stubbed toe, or trip to the store into a classroom in becoming aware of how I think, react, and feel. I continue to uncover pockets of bullshit that I’ve been carrying around for too long. It’s a process that will keep me busy for a long time.
But I see a better person emerging: Low stress, no fear, and more random daily moments of bliss than I ever thought possible. Recently, I found myself experiencing a new emotion: crying until I laugh. IFKYK.
And as I continue to wipe away the dirt and grime from the lens of my Self, I see more clearly how the world and all its people fit together in our complex adaptive systems. I have less worry and more optimism about our future. I think I’m making better business decisions now, too, even though this seems less important. Maybe there’s a connection there.
Recently, I had a conversation with the memory of my friend, Peter. He kept popping up in my dreams and iPhoto memories, which is usually a sign that I need to pay attention.
Peter was my business partner and the original founder of the agency that was my first entrepreneurial experience. He brought my friends, then me, in to help turn the company around and take advantage of the shift to digital marketing.
I’ve never met anyone more generous and more “happy to be here”—no matter where he was.
Peter was the first to leave the company after we completed the sale of our agency in 2011. Soon after leaving, he came up with a big idea that he was passionate about. He still had gas in the tank in his mid-50s and wanted to take a shot at a startup.
He used a part of his winnings from our agency sale to self-fund a small team of trusted alums from the agency to get the idea off the ground. As his beta product was coming together, Peter began to look for VC backing.
I ran into Peter a few months after I left the agency to do consulting with a VC firm in town. I, too, had a desire to start something, but didn’t have an idea yet. I figured some part-time work on the VC side would give me a useful perspective and connections.
One Friday afternoon, I caught sight of Peter as he was waiting in our lobby, preparing to meet with one of our partners. We greeted each other and traded a few words, promising to catch up more during our scheduled lunch the following week. As the elevator doors closed, I smiled at the sight of a giddy Peter, sitting there holding his laptop, awaiting his meeting. “That will be me someday,” I thought to myself.
But our lunch never happened. Peter suddenly passed away in his sleep a few days later.
I don’t know why he came to mind as I processed this story and my realization.
On one hand, Peter inspires me to keep pursuing dreams of a game-changing startup that can disrupt industries for the better. He loved his idea and the people he had assembled on his team.
On the other hand, Peter jumped from one company right into another. Was he, like me, looking for something to fill his time and need for meaning? If he knew he had so few remaining days on earth, would he be pitching for VC funding that afternoon?
Of course, I know that when I speak with him now, I’m only speaking with a ghost, a memory…myself. I miss him for many reasons, including the chance to get his perspective on things.
The one thing I do know: Peter had a love of life that is exceedingly and tragically rare. He was an old soul who kept a childlike playfulness. I’m not the man he was, but I want to be. So that’s my work now.
This summer I’m up in northern Michigan again. We’re in the woods, near a lake, and I’ve got a little office attached to a detached garage. For me, summer is wonderfully slow, and I have time for various personal projects. One of them is going through a big folder stuffed full of documents I’ve written over the years.
While sorting through them last week, I discovered some handwritten documents from that personal offsite I had in October 2019. I laughed and cried to myself as I realized how much progress I was making in personal development—a project that I left hanging as I jumped back into the startup grind for the next four years.
But I do not regret that “wasted” time. It was a necessary path to realization. We have recurring dreams at night because our unconscious is trying to get the attention of our larger selves and challenge us to change. The same thing happens when we repeat mistakes in waking life. Finally, mercifully, we sometimes learn to change course.
I can’t have that time back, but I have today.
And this time I’m learning a new trick. I’ve not retired from work yet, but I’m retired from the fight. Instead of wrestling with the gods, I’ve made peace and teamed up with them. No more standing against the stream of the universe, I’m now learning how to go with the flow. David Brooks calls it “Climbing the Second Mountain.”
I’ve now reframed my day job as “Working on being a better human, and testing myself through business.” It’s not the most comfortable thing to tell people you’ve just met when they ask what you do for a living, but it’s a mindset I wish I had adopted long ago.
This model mostly means being fully aware of what you are experiencing inside your own mind as you work—things like noticing how you react when employees ask for help, seeing the emotions come to mind when bad news falls in your lap, and watching how your energy levels and happiness change based on the tasks you do. Writing these things in a journal helps train your mind to notice at the time, then process and integrate the insights later.
This full-time job of self-discovery continues to bring me new epiphanies. For example, I’ve only recently realized how much I have identified with my career roles.
From Brand Manager to Agency Owner to Startup Founder. Each had its own Hero’s Journey, and each made me something “more.” But I spent too much time in these costumes, and should have spent more time in the roles of Husband, Friend, and Father.
Finally seeing this truth is helping me adjust for the better in several ways.
While we were all trading memes about the Astronomer CEO’s Coldplay fiasco, this video should have gone viral instead: An interview with Scottie Scheffler, the number one professional golfer in the world…
“Why do I want to win this tournament so badly? I don’t know.”
“The euphoria of winning only lasts a few minutes; you get to number one in the world and you’re like ‘What’s the point?’”
“Playing golf is not fulfilling in terms of the deepest layers of your heart.”
Replace “playing golf” with whatever you do for a living here, and you’d be on the right track to self-awareness. We are much more than our work.
And lest you think this mentality hurts one’s performance…well, Scottie went out and won another tournament the weekend after this interview. I think it’s proof that self-work works.
Nothing I’ve written here is meant to tell you what to do or not to do. Perhaps getting back on the horse immediately will lead to a billion-dollar idea that benefits a billion people. Maybe I’m just rationalizing my failures in a fancy pants way. You’ve got your own shit to figure out. I’m just a signpost here to help you see a tiny glimmer of something magic glowing in the corner of our everyday life. There is more to you than meets the eye in your mirror each morning.
Here’s a handful of things I wished someone had made me copy on a blackboard 1,000 times after my exit:
-
If you have enough money in the bank to take a year off, do it. “F.U. money” can also be interpreted as “Figure Urself out” money.
-
Trust the integration process. Give your mind time to reflect on the intense work you went through. Escape into nature as far away as possible and put your communication channels on OOO for a few months.
-
Do not rush to be an advisor, angel investor, coach, board member, etc. Sure, give people advice as they ask, but don’t turn it into a job yet! These commitments can last for years and may simply represent another rush to a role for the sake of the ego. Wait…and if it’s really your calling to help others, you will be 10x better once you spend real, quality time figuring your own self out first.
-
When people eagerly ask what’s next, tell them you’re “Pausing to consider options.” They will leave you alone. As you grow, you will stop caring about what people think.
You don’t have to have a startup exit to benefit from this advice. Every time you change jobs or consider doing so—perhaps even once a day—take a moment to reflect on how you feel. Are you happy with this role? Are you progressing, cycling, or reverting?
And try to find some separation between your role and your Self—whether you are a Brand Manager, Startup Founder, or Parent of Young Children. Each can be rewarding in many ways, but the more you cling to them, the harder it will be to shake free of the costumes when life moves on.
If you’re patient, curious, and willing to lean further—always further—into the dark places in your mind, you will find a light of truth that guides you to further insight, better decisions, and moments of bliss in work and life.
If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏
-
Fleet is our holding company for services businesses. We invest in leaders ready to start their own companies (we also do some M&A). If this might be you, hit my Office Hours link.
-
A2 Influence is our content development agency, helping some of the biggest brands and retailers create and distribute authentic content at scale.
-
Revelin is our consulting practice that helps with revenue alignment, growth management, and other RevOps functions.
-
Feel free to schedule a chat during my Office Hours to discuss questions, feedback, networking, or any other topic. Seriously, any topic! You can also reach me on LinkedIn or by email.
A little something I found meaningful. You might agree…
Vanilla Sky
A few weekends ago, while hanging with some old friends, we decided to re-watch a timeless, time-bending film that deserves more discussion: Vanilla Sky.
It’s one of those movies that keeps you guessing on the first watch and sticks in your mind long after. Subsequent viewing unlocks new insights, much like how we learn new lessons from reflecting on our past stories.
This time through, I felt more appreciation for the idea that life is but a dream. Whether asleep or awake, we are presented with situations that test us and offer opportunities to interpret and learn.
And if you seek assistance in the process, you might be lucky enough to encounter Tech Support.
