I used to call myself self-made. Built a company from nothing. Grew it to $15 million. Hired 50 people. Did it all on my own.
Except I didn’t.
TL;DR: Nobody is self-made. I built a $15 million company and called myself self-made for years. Then I started counting the people who made it possible and the list was longer than my business plan. The self-made myth is dangerous because it makes leaders forget the people who got them there.
The people I forgot to count
My stepmom Paula worked two jobs so I could graduate high school without worrying about rent. My first business partner put up $10,000 I didn’t have. A supplier gave me 90-day payment terms when I had zero credit history because he liked my handshake.
A foreman named Ray taught me how to read blueprints when I was 23 and too proud to admit I didn’t know how. A client gave me my first $100,000 contract based on a handshake and a recommendation from someone I’d done a $5,000 job for the year before.
Self-made? I couldn’t have opened the doors without these people, let alone kept them open.
Why the myth persists
The self-made story is seductive because it’s simple. One person, against the odds, through sheer determination. It sells books and fills keynote slots and looks great in a magazine profile.
It also lets successful people off the hook. If I made it on my own, I don’t owe anything to anyone. I don’t have to mentor the next kid coming up. I don’t have to share credit. I don’t have to acknowledge that luck, timing, and other people’s generosity played a role as large as my talent.
That’s a comfortable place to sit if you never examine it too closely.
What I tell young entrepreneurs now
When someone comes to me and says they want to start a business on their own, I tell them the same thing. You’re not going to do it on your own. And that’s fine. The job isn’t to do it alone. The job is to build something worth other people’s investment, whether that’s money, time, or trust.
Keep a list of the people who help you. Not metaphorically. Literally. Write their names down. When you make it, and I hope you do, go back to that list and make sure every person on it knows what they meant to you.
The real flex
I used to think strength was doing it alone. Now I think strength is building something so good that talented people want to be part of it. That’s harder. And it lasts longer.
The self-made man is a myth. The well-supported man who worked hard, got lucky in spots, learned from his mistakes, and had the sense to surround himself with better people? That’s real. That’s the version of the story worth telling.
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
Why is the self made narrative harmful?
Because it isolates leaders who are struggling. If you believe you should be able to do everything alone, you will never ask for the help that could save your company or your sanity.
How do you ask for help as a leader?
Be specific about what you need. Do not say I need help. Say I need someone who can look at my Q2 numbers and tell me where I am leaking margin. Specificity makes it easy for people to say yes.
Is it a sign of weakness to ask for help?
No. It is a sign of intelligence. The fastest way to solve a problem is to find someone who has already solved it. Pride is the most expensive thing a business owner can carry.
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Last updated: March 25, 2026