What happened when I stopped pretending to have it all figured out

I spent most of my thirties performing confidence. Board meetings, investor pitches, jobsite walkthroughs. I had a posture and a tone for each one. Different versions of the same act: the guy who always knew what to do next.

It worked, for a while. I built a roofing company from $1.5 million to $15 million. I hired 50 people. I stood on stages and told other people how to succeed. The whole time I was running on a combination of adrenaline and fear that someone would figure out I was making half of it up as I went.

TL;DR: I spent years performing confidence instead of practicing honesty. When I finally told my team I did not have all the answers, they stepped up in ways I never expected. Authenticity is not weakness. It is the fastest way to build a team that actually trusts you.

The moment it cracked

It was a Wednesday in 2019. I was running a pre-construction meeting for a project we had underbid by about $40,000. I knew the numbers were wrong. My project manager knew the numbers were wrong. But I sat in that room and talked about execution timelines like everything was fine.

After the meeting, my PM pulled me aside. He said, “You know we are going to lose money on this one.” I said, “I know.” He said, “Then why didn’t you say that in there?”

I didn’t have a good answer. The honest one was that I was afraid. Afraid that admitting a mistake would make me look incompetent. Afraid my team would lose faith in me.

So I kept performing. And we lost $40,000 on that project, plus the trust of a project manager who had been trying to help me.

What I changed

I wish I could tell you there was a clean turning point. There wasn’t. It was more like erosion. Slowly wearing down the need to appear perfect until what was left was just the truth.

The first time I told a team, “I am not sure what to do here, and I need your input,” I expected silence. I expected doubt. What I got was the opposite. Two people who had been quiet in meetings for months suddenly had ideas. Good ones. The kind of ideas that only come from people who feel safe enough to share them.

That taught me something I wish I had learned ten years earlier: my team was not waiting for my answers. They were waiting for permission to share theirs.

Why this matters for advocacy work

I carry this into my advocacy work now too. When I stand in front of a room and talk about losing my mother to gun violence, I can’t perform that. It’s real or it’s nothing.

Same thing on a jobsite or in a one on one with a struggling employee. People can tell when you’re performing. They might not call you on it, but they adjust. They hold back. They cover mistakes. They start performing too.

Before you know it, you’re leading a team of actors instead of a team that trusts each other enough to tell the truth.

What I tell new leaders now

You don’t have to have every answer. You have to be honest about which ones you’re still working on.

The performance gets exhausting anyway. I know because I did it for years.

If you’re reading this and recognizing yourself in the old version of me, here’s what I’d say: your team already knows you don’t have it all figured out. They’re just waiting for you to admit it so they can help.

Last updated: March 13, 2026