“Are you coming to bed tonight?” my wife asked. It was just after 10:00 p.m.
“I’ll be up. Eventually.”
She didn’t press. She usually doesn’t. I was in the middle of a problem for a client — again — knee-deep in a feature I swore I could finish before midnight. Two hours later, I finally pushed away from the computer. My shoulders ached, my brain was fried, and the issue was still unresolved.
That was the third night that week I’d told her the same thing, and it was starting to lose its meaning.
The only looming deadline was the one I’d created for myself. The client had been perfectly reasonable — happy to receive the product whenever I could deliver it. But I took their flexibility and turned it into something inflexible. If I didn’t finish it, I thought, it wouldn’t get done. And if it didn’t get done, the client would lose confidence. And if they lost confidence, we’d lose the deal. It always spirals that way — quietly, irrationally, and just below the surface.
I’ve spent most of my 25-year career believing that independence was the ultimate destination. After I left the company I helped found, I set out to build something entirely my own. As a solopreneur, working alone meant better margins, faster execution, and real-time decision-making. It has a clean, almost admirable air about it. But the truth is, it’s nearly impossible to deliver complex software projects on your own — at least not on any kind of promised timescale — because technical friction is always lurking.
There’s nothing scalable or sustainable about being a solo developer.
In the past six weeks, I’ve hired ten people — developers, client-facing staff, and an executive assistant I didn’t realize I desperately needed until she started. They’re better than I am at the things I used to grind through alone. They’ve solved in hours what used to take me days — or never got solved at all.
The first time I handed off a build and watched my team create something beautiful and functional, I felt a strange mix of elation and grief. The grief caught me off guard. For the first time, I had to admit that all those late nights hadn’t made me faster or better. I was just spinning harder.
I swore to my executive assistant that I’d stop checking my email forty times a day. I think I’m down to ten. The voice in my head tells me that’s part of why I hired her, but when I see she hasn’t checked email in two whole hours, I have to fight the urge to respond to a client who neither needs nor expects an urgent reply.
Still, I think: I should just take care of it. I should be the one to solve it. If I were better, faster, smarter, and more technical I wouldn’t need anyone else. So I stay up later than I should, telling myself it’s just “one more time”, even though I know better.
It never is.
The most persistent story in my negative self-talk is about fear — specifically, the fear of becoming unnecessary. If I’m not the one fixing things, what value do I bring? If I’m not essential, then what am I? I usually mask that fear behind a threadbare veil of commitment, integrity, and work ethic. But at the core, it’s just fear.
A few years ago, I wrote an article about self-actualization — the idea that we should strive to become everything we’re capable of becoming. I argued then that the pursuit can go sideways, turning into perfectionism, obsession, or even selfishness. I thought I understood it at the time. But I see it more clearly now.
Independence, I’ve learned, can become a shield. A defense mechanism that looks like strength. If I do it myself, I don’t have to ask. I don’t have to explain. No one can slow me down, and no one can let me down. But no one can help, either. And eventually, I forget how to let them.
That night, after not shutting the laptop, I stood in the dark kitchen, hands resting on the counter, staring into the quiet of our home. Everyone was asleep. I’d missed everything. Again.
And for what?
The problem I was working on wasn’t urgent. It could’ve waited until morning. Honestly, I could’ve left it for a few weeks and my team would’ve solved it faster than I was attempting to. But I stayed up anyway — not because I had to, but because I was afraid to stop.
I worked tirelessly on that issue for days with no resolution. Then I handed it off to two exceptional developers I’d just hired. They solved it in four hours.
I’m finally starting to accept — though I still forget a lot — that I have strong instincts and experience for helping clients solve real problems, but I’m not always the best person to code the solution. I’m learning it’s okay to step away. To not eat lunch at my desk. To go for a run again. To let my body sleep an extra hour when it needs it.
I love my work. It brings me so much satisfaction. I derive a lot of my self-worth from helping others solve complex things they can’t solve for themselves. So yes, I’ll still work late sometimes. I’ll still feel the impulse to fix everything myself. But I’m also learning to trust the team around me. To pause before I jump in. To recognize when someone else is better equipped to take the lead.
They’ve given me the space to do that. To say “I’ve got it” less often. To let them help. And we are so much stronger together than I ever was alone.
The independence that helped me start this business isn’t the same thing that will help it grow. And it’s certainly not the thing that will keep me healthy doing it. That version of independence — the one I built my early success on — started to turn into something smaller. Something isolating. I didn’t mean for it to, but it did.
Now, I’m unlearning that. Slowly. Imperfectly. I’m beginning to believe that the goal isn’t to be needed everywhere, but to be trustworthy where it matters most. Maybe the best kind of leadership isn’t about proving I can do it all — it’s about creating space for others to thrive.
I’m still figuring it out. Still letting go of old habits. Still learning to ask for help without apology.
And that is enough.
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