What Would You Tell Your 20-Year-Old Self?

Stephen Leonard in 1997
Stephen Leonard in 1997

I recently joined a gym and as part of the intake one of the guys asked me, “Stephen, what would you tell your 20-year-old self?” His question made me reflect on 20-year-old Stephen. “What would I want him know—in college, trying to figure out how he’ll live in the world?”

Then it came to me, “Take more risks. I would tell 20-year-old Stephen to take more risks.”

I think back on classes I thought about taking but didn’t. The semester in the U.K. that I always wanted to do, but “couldn’t ever afford.” The girl I wanted to date, but couldn’t risk being rejected. The job I wanted, for which I never applied.

Hockey player Wayne Gretzky said, “You miss 100 percent of the shots you never take.”

How often have you missed out on an opportunity in life, not because you failed, or lacked the skill, or got beat out by someone more qualified, but because you never tried? In my life that’s true more often than I would like to admit.

I don’t want to be laughed at. I don’t want to be criticized. I can tell you every objection to every risk I take. Whether big or small, there’s always a reason to hold back, play it safe, and avoid finding out what I’m really and truly capable of doing.

But I also know risk works. That’s how I met and married my wife. That’s how Lisa and I built our business to the point I could leave my day job. That’s how we help the people who stare understand David and respect people with special needs. That’s how I got fired from one job to get a much better one.

Here’s the thing about avoiding risk—it’s impossible. Safety is an illusion. Life is risky. People are killed in automobile accidents everyday. I know an athletic and otherwise healthy 22-year-old who suddenly died days before college graduation. I’ve seen people in the intensive care unit for heart problems caused by stress. I’ve seen leaders endure criticism, failure, and loss as a result of avoiding risky decisions that they believed in. I’ve spoken with people in their late 80’s who characterize their lives with regret because they avoided the risk of the path they really wanted to follow.

Yes, we need to be responsible in our risk. Start small. Write a blog. Take that trip you’ve always to take. Volunteer your time in a cause you care about. Invite those people for dinner you’ve been wanting to get to know.

If I were to give my 20-year-old self advice, that’s what I would tell him. Risk more. Risk in the little things to gain practice. Learn from failures in risk. And risk again.

I’d love to hear from you. What Would You Tell Your 20-Year-Old Self?


  1. Great blog Stephen! In the middle of taking some personal risks right now – thanks for the reminder. Glad the in take questions spurred your blog topic too!

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