How I stopped letting imposter syndrome run my career
The first time I walked into a corporate boardroom to pitch a commercial roofing contract, I was wearing a polo shirt and work boots. Everyone else was in suits. I sat down, opened my binder, and spent the first ten minutes convinced they were about to ask me to leave.
TL;DR: Imposter syndrome ran my decisions for years. I overcompensated with performance instead of addressing the fear underneath it. The shift came when I realized the feeling never goes away. You just stop letting it drive.
Where it showed up
It showed up in construction. I started Penebaker Enterprises without a business degree, without investors, without a mentor who had done what I was trying to do. Every time I won a big contract I waited for someone to figure out I was winging it. Every time we hit a revenue milestone, I moved the goalpost because the current one felt like a fluke.
It showed up in politics. Running for Congress in WI-5 without a political background, without connections to the party establishment, without anyone in my family who had run for office. I would stand at candidate forums and think: everyone here has a law degree and I have a roofing company. Who do I think I am?
It showed up on stage. The first dozen speaking engagements, I would prepare for weeks. Not because the material needed that much work but because I needed to feel like I had earned the right to stand there. I was over-preparing to compensate for a feeling that had nothing to do with preparation.
What I was actually doing
I was performing competence instead of accepting that I already had it. Every hour I spent over-preparing was an hour spent managing the fear instead of doing the work. The company grew to $15 million not because I was faking it. It grew because I knew what I was doing. But the voice in my head kept insisting that the growth was luck and the next failure would prove everyone right.
That voice made me work 70-hour weeks when 50 would have been enough. It made me say yes to projects we should have passed on because turning down work felt like admitting weakness. It made me avoid asking for help because asking meant admitting I did not know something.
What shifted
A friend told me something I did not want to hear: “You are not afraid of failing. You are afraid of being seen failing.” That landed differently than the self-help version of the same idea. He was right. I could handle failure. I had failed before. What I could not handle was other people watching it happen.
Once I named the actual fear, it got smaller. Not gone. Smaller. I still feel it when I walk into a room where I am the only one without an Ivy League degree or a corner office. The difference is I do not let it make my decisions anymore. I feel it and I move anyway.
The feeling never goes away. You just get better at ignoring its advice.
About Khary Penebaker
Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership experience in construction, operations, and civic engagement.
Frequently Asked Questions
Do successful people have imposter syndrome?
Constantly. Research suggests 70 percent of people experience it at some point. The difference is not that successful people eliminate it. They just stop letting it make their decisions.
How do you deal with imposter syndrome as a leader?
Name it. Out loud if you can. Tell a trusted person that you feel like a fraud. The moment you say it, it loses most of its power. Then look at the evidence. Your track record exists for a reason.
Is imposter syndrome worse for people who are self taught?
Often, yes. When you did not follow the traditional path, you assume everyone else knows something you do not. The truth is most people are figuring it out as they go regardless of their credentials.
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Last updated: March 13, 2026
