Why (and when) you should enmesh your identity with your startup
Welcome entrepreneurs! I’m so glad you’re here.
They say that you should build a healthy separation between your identity and your company. That’s the very work I often do with later stage founders — supporting them in looking deeply at the whole of their lives, and properly orienting to their work within.
But that approach isn’t for everyone. Some of us are, as they say, “all in.” Like I was for my first nearly 20 years in startups.
For those ambitious ones, the ones who are willing to sacrifice everything to make their company successful, I salute you.
This essay is for you.
Fully becoming your company and swinging for the *bleeping* fences may be the best thing you ever do
From the second I launched my first startup, and my second, and my third, I fully enmeshed my identity with the identity of my company. It was my ticket to becoming SOMEBODY.
If you had asked me during those years who I was, I would have told you I was the founder of XYZ company (depending on which one it was at that point), and my purpose in life was to make that company successful. I was here to put a dent in the universe. More specifically, I was here to be the guy who had.
Looking back on their own paths, many older and wiser people told me that I had my priorities all wrong. That my company existed within the context of my life, rather than the other way around. I myself, from my current, somewhat more experienced if not wiser, vantage point, have said exactly that.
And it’s true. Only, at that time in my life, I wasn’t able to hear that message.
When you’re laser focused on making something of yourself and building something big and impactful, people whispering things like that at you from the sidelines seem off their rockers. You’ve got a company to build, and goddamn it, YOU can be the one who changes the world. Somebody’s got to.
And so, to those founders deep inside the early career chase, I say:
Enmesh your identity fully with your startup. Attach all your self-worth and identity to the accomplishments of your business. And then swing for the fucking fences.
Ride the highest ride that capitalism can offer. Tame the beast. Fly all the way to the sun on the back of your startup. Become all that you can be, truly. Burn your boats. Leave no stone unturned.
Do everything to win.
If you do this, truly and honestly…you can’t lose.
The binary outcomes of fully enmeshing your identity and shooting a moonshot
I recognize that this is counterintuitive – when I’ve said similar things to friends or on the Internet, I get confused looks and a bunch of “huh?” comments, because it flies in the face of most of the conventional wisdom.
But if you swing for the fences, one of two things can happen.
First, you can hit. If this happens, you become a millionaire. You participate in one of those generational wealth creating events that happen more than you think, and you set yourself and your family up to have one less thing to worry about.
Or you can miss. Despite all your efforts, you can come up short and lose it all. You go broke, lose stature, and deal with mental and physical health challenges. This sounds unpleasant, and it is. But if you have appropriate distance between yourself and your company, that’s all it is – unpleasant.
Only, if you’ve thoroughly enmeshed your identity with that of your company, there’s an upside to missing. If you’ve become one with your organization in such a way that it dying is akin to you dying, something amazing happens: as you whiff, you experience rapid ego death. Which, in the scheme of your life, may be the greatest gift you’re ever given.
Ego death as a result of company death
Man has two lives, his second begins when he realizes he only has one. – Confucius
There are two most important days in a person’s life. The day they’re born, and the day they find out why.
It’s impossible to know when that second day will be, but I can say from experience (both personal and secondary having escorted dozens of founders through this process as a coach) that that day will come on the heels of ego death.
Why? Because in the early stages of your career, you are not living your life. You’re living a predefined life based on the career choice you’ve made, the city you’ve moved to, and a few other major choices. Within those major choices are a multitude of value frameworks that tell you what to want based on what other people like you have wanted, smuggled into your own values like a Trojan horse.
And to figure out why you, individually, were born, you have to outgrow this social frame and learn who you are. Deeply, and quite separately from your career or your house or your friends and your bank account. This benign sounding process actually feels quite like you’re dying, because all the things that you thought were important and True about yourself turn out to be undeniably artificial, and fall away.
Painful as this process is, only once you’ve seen through the parts of “yourself” that were inherited from your environment and influences, can you finally find what’s true..
As they say, you have to die a little death, in order to finally live your true life.
Dying (no matter the size of the death) is something we humans tend to avoid, so for most people, this process takes decades. Well into middle or old age. For many, they never figure this out, and die clinging to the notion that their status amongst their social group was the point of it all, simply because they were too scared to explore something deeper.
But that’s the magic of high stakes, venture backed entrepreneurship. It gives you the opportunity to enmesh your very sense of self with your company – with a thing that has a 90% chance of dying, and even if it’s successful has an outside shelf life of 10-15 years.
And if you do so, whether it ends with fireworks and trumpets, or death and destruction, it will end.
And you will be forced to reckon with what’s left behind. To shed all those parts of yourself that you thought were true, and learn who you truly are.
By projecting your sense of self onto a thing that lives only 10 years, you commit yourself to dying a little death before you actually die, and finally finding out why you’re here.
That’s the true purpose of startups, from where I’m standing. They’re the most powerful and reliable engine for spiritual growth that capitalism has yet produced.
Firecracker exit or shutdown, when you play the startup game full out, you can’t help but win.
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