Learning to Delegate

I'm not good at delegating.

I know I should be. I've read the books, listened to the podcasts, heard the advice a hundred times. Intellectually, I get it: trying to do everything yourself is great way to burn yourself out.

And yet, handing things off to other people still doesn't come naturally to me.

This is something I'm actively working on, so I figured I'd write about it honestly. I suspect I'm not the only one who struggles with this.

The full-stack founder problem

I recently came across the term "full-stack founder," which basically describes someone who can do a bit of everything: code, design, marketing, sales, ops. That's more or less me.

It's a blessing and a curse.

At my first startup, Simpo, I rarely let go of things. Even when we had 21 people on the team, I was still doing tasks that made zero sense for a CEO to be doing. Editing data in Salesforce for hours. Reviewing every piece of copy. Getting involved in decisions I had no business being part of.

I told myself it was because I cared about quality. That no one else would do it as well as me. That it was "faster to just do it myself."

Because I could do most things reasonably well, there was always a justification. That's the trap, really. When you're decent at a lot of things, there's always a reason to just do it yourself.

Looking back, though, those were just stories I told myself. The real reasons were messier.

The fear underneath

The truth is, I was afraid.

Afraid that if I handed something off, it wouldn't get done right. Afraid of losing control. Afraid that if I wasn't involved in everything, I'd somehow become irrelevant.

There was also a perfectionism thing going on. I built the company from nothing. I had strong opinions about how things should work. Trusting someone else to execute felt like giving up control of something I'd put my whole self into.

And honestly? I had trust issues. Not just with my team, but with people in general. Life had taught me that depending on others often led to disappointment. So I defaulted to doing things myself.

What it cost me

All of this caught up with me eventually.

Five years into Simpo, I was so burned out I wanted to shut the whole thing down. We still had millions in the bank, but I had no energy left. I'd spent so much of it doing everything myself that I had nothing left for the things that actually mattered: strategy, product vision, being present for my team.

My difficulty delegating didn't just hurt me. It hurt the company. I became a bottleneck. Smart, capable people on my team couldn't fully step up because I wouldn't get out of the way.

What I've learned (so far)

I wish I could tell you I've figured this out. I haven't. But I've made some progress.

The biggest thing that helped was therapy. I know that sounds cliche, but understanding why I had such a hard time trusting people, where that came from, made it easier to catch myself in the moment. To recognize when I was holding on to something out of fear rather than necessity.

I've also gotten better at sitting with the discomfort. You know that anxious feeling when someone else is handling something you care about? It doesn't fully go away. But I've learned to not act on it, at least sometimes. To let things play out instead of jumping in to "fix" them.

What surprised me is that when I do let go, things often get done differently than I would have done them, but not worse. Sometimes better, actually. That's been humbling.

I'm still working on it

I don't want to pretend I've got this figured out now.

I still catch myself taking on things I should hand off. I still have moments where I think "it's just easier if I do it." Trust is still hard.

But I'm more aware of it now. And awareness is the first step.

If you struggle with this too, you're not alone. It's hard. It goes against a lot of the instincts that made you successful in the first place. But learning to let go is part of the job.

I'm still learning.