If you believe the saints
Welcome Entrepreneurs, I'm so glad you're here.
Leaving the company I founded was one of the most painful experiences of my life, in part because my sense of self had become so intertwined with my role as CEO of VNN. The obvious answer to this would be to, um, not do that. But with some distance I'm not sure that's the right approach.
Having gone through it, I'm wondering if becoming one with your company is actually one of the most useful things you can do.
Let's dive in.
If you believe the Saints, starting a startup may be the most effective thing you can do with your early life.
Spiritual teachers from all the world’s major wisdom traditions have a similar message, distilled by Eckhart Tolle in the following way: “the secret to life is to die before you die.” This refers to the idea that all of early life is something besides your actual life. Often it’s an elaborate bit of play-acting in which you try really hard to win whatever game you think you’re playing – business or science or writing or whatever – never questioning the fact that winning will satisfy you.
You can stay on this treadmill for your entire life. But these same spiritual teachers speak of a different way – of going beyond this type of life. This alternate path begins by discovering who you truly are and wholly embodying yourself, usually for the first time, and demands that you live in alignment with what you find.
“A person has two lives. The second one begins when they realize they only have one.” – Confucius
Jesus’s story, for example, is one of rebirth after death. Taken metaphorically, it’s a perfect example of a phenomenon we see throughout history: people being fundamentally changed by having a brush with mortality. Joseph Campbell compiled myths from hundreds of civilizations into an archetype of the universal human journey into death and rebirth (do yourself a favor), calling it the Hero’s Journey. This journey isn’t just a myth; it’s the single story that permeates humanity throughout millennia.
For many, the journey requires a legitimate brush with death. A car crash from which you walk away. A bout with malignant cancer. But it’s also possible to begin the journey with a different type of death: ego death. Either way, it takes confronting the idea of your own mortality, not intellectually but viscerally. Feeling the terror, that sinking pit in your gut that tells you this is The End.
It’s the hardest thing you’ll ever do, dying, but if you believe the single story that humans have been telling down generations since time immemorial, dying this type of death to truly wake up to your life is the main thread of being a human being.
When I began to share my story of being fired from the company I’d founded, and the existential vacuum left in its wake, so many people nodded sagely. “Yeah,” they’d say with a knowing grimace. “It’s so easy to wrap up your identity in your company.” Some said they wished there were training for early founders about how to have a “healthy relationship” with one’s company. At that stage in my grieving process, I agreed wholeheartedly.
But looking back on what was undoubtedly the most painful experience I’ve ever had, an experience which took years to process and involved me dying more than one painful death, there’s no question that it was also the most formative experience of my life. When I was no longer the CEO of my company, a part of me died, the part of me that I thought was all of me, and I got to see life on the other side. By intertwining my identity with my company, I had unknowingly put myself in the position to die an ego death similar to any near death experience, and then to be reborn. But without all the risk of, you know, actually dying.
Looking at the process now from the other side, I’m wondering if we have it wrong.
If you believe the Saints, maybe we SHOULD be wrapping our identity up as tightly as possible with our companies, and swinging for the fences. Either we leave a dent in the universe (super appealing to the young, ambitious ego), or we die an ego death in the attempt. It’s the most painful thing you’ll ever experience, but if you believe the Saints it may also be the capital-P Point of living.
I’ve heard similar stories from other founders, those whose companies failed and those who exited with a financial windfall. The circumstances of their exits seem to matter less than the amount of time the founder took to thoroughly enmesh their sense of self with their company. If a founder has been running his company for a while, stepping away, whether all at once or gradually, creates an opportunity. The person you thought you were dies. There is no mistake about that. And you have perhaps the opportunity of a lifetime to choose to go beyond.
Most don’t, to be fair. The instinct to start another company immediately after leaving your company is immense (I’ve written about this here), and most simply hop right back on the treadmill. With one taste of death, their ego gets to work spinning up another impressive person to be. Another role to spend one’s life playing. But some, and more than I expected, choose the red pill. Some use their death as the CEO of their company to catapult them to their real life.
“You must let go of the life you have planned, to have the life that is waiting for you.” – Joseph Campbell
True entrepreneurs are artists who produce at scale. Sure, there are functionaries and hacks who figure out how to build systems to make money. Our society and economy wouldn’t function without them, so I harbor no judgment. But true entrepreneurs have more in common with painters than those functionaries. Painters using bigger, more complex brushes. And of those true entrepreneurs making art at scale, there is an even smaller, more precious subset, who have done their Work. Who have undergone their own Hero’s Journey, died their ego death, and have reaped their reward.
Vocation.
The soul-deep imprinting of why a person is here, and what Work a person is to do with their life. Upon finding their vocation, that’s when a person’s second life begins. Their true life.
And maybe that’s the real opportunity of startups. The opportunity to thoroughly dedicate yourself to building something that matters, so much so that your identity is hopelessly intertwined with the success of the thing you’re building. To dedicate yourself to your cause so thoroughly that you can’t imagine living without it finding success. To say the hell with it and jump into the pit headfirst. Because either way, whether your startup succeeds or fails, what’s on the other side is worth it.
There’s a reason the teachers say that the most valuable treasure of your life is guarded by dragons. This most precious of gifts, vocation, is fucking expensive. Death is the cost of entry. But if you believe the Saints about what’s important in life, and you’re committed to doing what it takes to claim your gift, dedicating yourself wholly to your startup seems to me much safer than battling cancer.
Things I read this week
One: Are founders allowed to lie? (Alex Danco)
As a CEO, the need to pitch the future as if it's inevitable while being confronted daily with all the reasons it'll never happen can create a cognitive dissonance that feels like lying. Is this OK? And how does all this relate to medieval kings and priests? (I loved this article)
LINK >>
Two: How to break free of the cognitive-emotive loop (Conscious Leadership Group)
Ever see someone become righteously indignant, and then completely lose their ability to think objectively? Being right, to them in that moment, is more important than anything else. Ever been that person (raises hand)? Here's what's going on and how to solve.
LINK >>
Three: The Bio-Emotive framework
So much of cognitive freedom is effectively metabolizing emotions. This is the first framework I've found that purports to help folks train to do that effectively. (caveat I haven't used it, but the theory of it makes sense -- if you do use it, let me know how it works).
LINK >>
Four: Can leaders have hobbies? (PsychologyToday)
Intuitively, I went into this article with a firm yes, because my own experience is so stark: as I've gotten more breadth in my life (hobbies, yes, but also and primarily kids), I've found myself more creative and more effective in less time. Still, it's nice to have all the research backing up my intuition here.
LINK >>
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