The Checkered Childhood: How Survival Made Us Entrepreneurs (And Why It's Time to Graduate)
Though it’s been more than 40 years, I can almost feel the moment like it was happening today. The first time the world failed to meet my expectations.
The instance I'm referring to was the jarring experience of school, kindergarten to be exact. Up till this point, I was, to my knowledge, the center of the universe. After all, as a young kid with no other kids to compete with, you might as well be the only kid on the planet. That is, till you are thrust into a classroom with 20 other confused kids. For me, that was chaos. And it was a foreshadowing of the next few years. I was never going to fit in.
Some might say this was exacerbated by the fact that I had no father, because he was in prison. I had no idea how to be a boy; I had to learn myself. I had a mother who loved me dearly, but had to work what seemed like 17 jobs just to cover the gap, so I saw her sparingly. Luckily, she was from a large family, and it felt like I was evenly distributed across any and all available relatives who could fill the role of daily caregiver. Still, to them, I was more a burden, and I was left to be as a burden would be.
That whole paragraph to say, I learned real quick that my needs were my own, and that I would take care of myself. In essence, I learned to overvalue resources and undervalue love and connection. After all, love didn't really look like connection to me in those days. Couple this with a struggle to fit in and you have a boy who learns that people don't like you for who you are, they like you for what you have. And from about the age of 5 onward, I learned to amass things the other kids couldn't because they seemed to like me more because of it.
I learned to hustle real quick. I learned that who I was inside was worthy of ridicule, but what I could pull off was commendable. I stockpiled the early goods that turn a child into a king — candy bars, cash, and capability. Granted, I was still socially awkward and uncomfortable — so next, I learned rage and aggression. Then I became known as the kid who protects others, provides resources, and was capable of pulling off the un-pull-off-able.
Fast-forward 40 years, and I'm still trying to unwind that fuckery.
If I'm being honest with you all, I didn't realize the implications of these early years until very recently. I did, however, notice a recurring pattern that seemed to follow me, which for the longest time I wrote off as "people be peopling."
That pattern was I amass and collect resources, attract people in pursuit of opportunities, together we build something great, and then I struggle with feelings of worth, doubt, and inadequacy, so I subconsciously break said great thing. Disappoint the people who were attracted to me. Become their villain. And reinforce my internal narrative that I am just not "good enough." And repeat.
In fact, every time I meet a self-proclaimed "serial entrepreneur," I chuckle and think to myself, "Oh, you too,” because I know what that usually means: get in, build something super quick, and if you’re lucky, exit before you have a chance to break it. Repeat till complete.
But it's that last part. What is complete?
This all might read more like a journal entry than a blog post, but I assure you there is a point — and I also know many of you share the same story. Most of us became entrepreneurs not out of desire but necessity, the continuation of a checkered childhood.
Which leads us to the paradox of the notion of completion — because there is no end in sight until we release that checkered past. For most of us, this is hard. Because what we’re talking about is no doubt childhood trauma, but unlike some more severe forms, we ended up with a highly productive result. We saved our own lives. Many of us became quite successful.
But if you’re reading this, I suspect that success didn't seem to solve the phantom problem. The feeling of incomplete fulfillment.
Here's what I've come to understand. That little boy who learned to hustle candy bars and build an empire of capability? He wasn't chasing success. He was chasing something far more primal. Connection. Worth. The feeling that he mattered — not for what he could provide, but for who he was.
But chaos doesn't teach that lesson. Chaos teaches survival. And survival, by definition, is about resources, not relationships. About proving, not belonging.
So we grow up. We scale our candy-bar empires into actual businesses. We trade recess dominance for market dominance. And we keep running the same program, wondering why no amount of revenue, recognition, or exits ever quite fills the void.
We call ourselves “serial entrepreneurs" like it's a badge of honor. And maybe it is. But it's also often a confession. A confession that we haven't figured out how to stop. That we've mastered the Function of building — the systems, the strategies, the hustle — but remain trapped in a Structure wired for survival, not fulfillment.
This is what I mean when I talk about Person Before Process. Most of us have maxed out our obsession with function. We've read all the books, implemented all the frameworks, hired all the consultants. We can run circles around "best practices." And yet, we still find ourselves sabotaging the very thing we built, disappointing the very people we attracted, and reinforcing the very narrative we've been trying to outrun since kindergarten.
Because no system can outperform the operating system running beneath it.
The little boy who learned that his worth came from what he could provide? He's still running the show. And he's exhausted. He's been running for 40 years, and he still doesn't feel safe enough to stop.
So what is complete?
Complete is not another exit. It's not another venture. It's not more resources or recognition.
Complete is knowing what that little boy actually wanted before the world taught him to adapt. Before chaos became his comfort zone. Before he learned to overvalue resources and undervalue connection.
Complete is what I call Ecology: the authentic desires that are truly yours, not borrowed from survival or copied from others in an attempt to prove worth. It's the difference between building what you think will finally make you enough and building what actually fulfills you.
Most entrepreneurs spend their lives chasing mimetic goals — pursuits borrowed from external validation, industry standards, what "successful people" do. We copy what works for others because we never learned to trust what's true for us. We chase more because we don't know what enough actually looks like. We stay distracted with tactics because sitting still long enough to feel the real question is terrifying.
The real question: Who would you be if you didn't have to prove anything to anyone?
That's ecology. That's traction. That's complete.
The hard truth: You probably can't see this on your own.
Not because you're not smart enough. You're brilliant. That's actually part of the problem. The same capabilities that helped you survive and build have also helped you construct elaborate justifications for why the pattern keeps repeating. You can analyze anything except the lens you're analyzing through.
This is where a coach becomes invaluable — not as another consultant adding more tactics to your already overflowing toolkit, but as someone who can help you see the difference between Structure and Function. Someone who can see between the survival patterns still running the show to the authentic desires waiting to be discovered beneath.
A good coach holds up a mirror, but not the mirror you've been looking at your whole life, the mirror that shows what you've accomplished. They hold up the mirror that shows who you are without the accomplishments. And they help you see that person isn't the burden you were once treated as. That person is actually the point.
If any of this resonates, if you've felt the phantom incompleteness despite the external success, if you've recognized yourself in the serial entrepreneur confession — you're not alone. And more importantly, you're not broken.
You're just running outdated software that was installed during a time when survival was the only option. The good news? You can update it. The even better news? You don't have to do it alone.
Find Your Ecology
At Paradigm Collective, we specialize in helping high-achievers move from survival to fulfillment — not by adding more tactics, but by helping you see what's actually driving the machine. Our Diagnostic is designed to identify where you are on the journey, what's keeping you stuck, and what genuine completion might look like for you.
And if you're tired of the isolation that comes with this particular brand of success, our FirePits bring together people who get it. No pitching, no pretending, no performance — just real humans around real fires in remarkable places, sharing the real journey. Because sometimes the most powerful thing isn't another strategy session. It's sitting with people who understand — because they've lived it, too.
Ready to discover what that little kid you once were actually wanted?