I have built companies, coached leaders, and sat at the top of sports and entertainment. I’ve also lost everything and rebuilt. The lesson I carry from both peaks and valleys is simple: humility moves you faster than ego ever will. If I had to start over today, I wouldn’t need decades to get back. I’d get there quicker, because I now live by a different rule: ask for help and become your own best mentor.
As Chairman of the Napoleon Hill Institute and former CEO of Leigh Steinberg Sports & Entertainment, I’ve seen how pride delays progress. What accelerates it is honest reflection and open questions. That’s my stance. Real speed comes from humility.
My Case for Humble Ambition
I learned a hard truth after I lost everything in my thirties. The second climb was faster. Why? I stopped pretending I had every answer. As I like to say, you only can connect the dots backwards.
“You only can connect the dots backwards.”
That shift began with a decision: become my own mentor. I examined past choices, patterns, and blind spots. Then I took it further. I started asking people who had already been where I wanted to go what they would do in my place.
“I became my own mentor.”
“Why not ask someone that sits in the situation next time I’m in it what they would do?”
Earlier in my career, I acted like a Midas. I was a millionaire nine months out of law school and thought I knew everything. I hadn’t tasted real loss, so I didn’t ask for help. That arrogance cost me time, money, and peace.
“I was a millionaire nine months out of law school so I thought I knew everything, I never lost money, so I never really asked for help.”
Today, my calendar looks different. Half my day is giving help. The other half is asking for it—calling mentors, searching, reading, listening. Humility isn’t staying quiet. Humility is asking.
“Now, almost all my day is not only giving help, the other half is asking people… They think they’re humble not for asking, I say humility comes from asking.”
What Actually Speeds Up Success
I’m not pushing theory. I’m sharing what saved me time on the climb back up. Asking shortens the learning curve. You borrow hard-won lessons without paying the same price. You avoid dead ends. You see the next step clearly.
Some argue that self-reliance is the only path. I agree we must do the work. But going it alone is not strength; it’s a stall. Every great performer has coaches. Every smart investor has advisors. “Figure it out yourself” sounds tough. It’s actually slow.
Here’s how I apply it every day. These steps keep me grounded and moving:
- Start with review: write one lesson from yesterday and how to apply it today.
- Ask one direct question to someone who has done what I’m trying to do.
- Set a clear ask: time, feedback, or a single introduction—never a vague request.
- Give help before I need help. Service builds trust and teaches faster.
- Measure progress in learning, not just income. Money follows skills and habits.
Each step turns humility into action. Taken together, they create speed with fewer regrets.
The Ego Tax You Don’t See
Ego charges interest. It keeps you from learning until the market, or life, delivers the bill. I paid that bill once. I won’t pay it again. My toughest days pushed me to ask better questions and listen longer.
My rule now is bold and simple: if someone has the answer, ask them. Then act. That’s how compounding wisdom works. One right decision leads to the next, and momentum returns.
Final Thought
You don’t need another decade to get where you want to go. You need clear reflection and honest asks. Become your own mentor. Seek people who sit where you want to sit and learn their playbook. Then execute with discipline and kindness.
Drop the ego. Ask for help. Move faster. Start today by writing one lesson from yesterday, and send one question to someone who has already done what you’re trying to do. Your future self will thank you for the speed.
Frequently Asked Questions
Q: How do I become my own mentor in practice?
Start a daily review. Capture one win, one mistake, and one action for today. Over time, your notes become a personal playbook you can trust.
Q: What’s the best way to ask for help without wasting someone’s time?
Be specific. Ask one clear question, provide brief context, and suggest a short window, like a 10-minute call. Make it easy to say yes.
Q: How do I keep my ego from blocking progress?
Use triggers: when you feel defensive, pause and ask, “What can I learn right now?” Replace posturing with curiosity and a single follow-up question.
Q: What if I don’t have access to high-profile mentors?
Start local and digital. Join groups, listen to interviews, read books, and reach out to one level above you. Consistent small asks lead to big guidance.
Q: How can I tell if I’m moving faster with this approach?
Track decision speed and error rate. If you decide quicker and repeat fewer mistakes month over month, humility is paying dividends.
