He Went First

How a former mentee became one of my most important advisors

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It was August 2023. The kind of sticky evening in Orlando, Florida, where your shirt clings to your back as soon as you walk outside.

John Oliver and I were having dinner near the pool after a full day at a Maxwell Leadership conference. We’d just heard James Clear speak about getting 1% better every day. Small steps. Atomic habits. The stuff that changes your life when you actually do it.

I looked across the table at John and thought, “This guy is special.”

He was 26 at the time. I was 54. He’d come through the engineering rotational program I was leading at my company. I was supposed to be his mentor. That’s how it started, anyway.

But sitting there talking about the future, about what our lives could look like, something seemed different. I realized we weren’t in a mentor-mentee relationship anymore. We were two guys sharpening each other. And honestly? He was sharpening me more than I was sharpening him.

The Reversal

Tim Elmore writes about this in his book “A New Kind of Diversity.”¹ He calls it reverse mentoring. The idea that wisdom doesn’t only flow from older to younger. Sometimes the 26-year-old has something the 54-year-old desperately needs to hear.

I experienced this firsthand with John.

After that conference, our relationship deepened. We talked almost every week. Books we were reading. Podcasts that had shifted our perspective. Our shared faith in God. Where we felt stuck. The kind of conversations that go deep and make you better.

A year and a half later, John did something I wasn’t ready to do.

He left.

He went all-in on building a ghostwriting business. A young guy in a young marriage, betting on himself. I found the text he sent me:

“Man, I’m doing it. I’m gonna put in my 2 weeks. I’m going after this thing. I have my date on the calendar. And it’s close.”

And then this one:

“Your turn is coming. I’m gonna be pushing you soon enough!”

He went first. And by going first, he gave me permission to follow.

What John Taught Me

Here’s what a twenty-something guy taught a fifty-something guy with 21 years at the same company:

Age and experience don’t mean you have all the answers. I’d spent decades assuming the wisdom flowed in one direction. Older to younger. Leader to team member. I was wrong.

Sometimes you need someone to go first. I could talk myself out of anything. John couldn’t talk himself out of his calling. Watching him take the leap made my own leap feel possible.

The person you want to become is on the other side of your discomfort. John sent me that line during one of our conversations. It stuck. Who I wanted to become wasn’t going to show up while I played it safe.

After 21 years at my company, I finally left last week. John was one of the first people I heard from:

“I look back on that time as a ‘such a time as this’ moment where God put both of us in each other’s lives... If you feel feelings of anxiousness, just surrender it to the Lord. I’m working on that right now myself. Trust in His provision. I’m so excited for you, so proud of you, so inspired by you.”

That’s reverse mentorship. Someone half my age. Encouraging me. Pushing me. Walking alongside me.

The Lesson

If you’re looking for mentors, don’t just look up. Look around. Look at the people coming behind you.

Over 10 years of leading an engineering rotational program, 130 engineers came through. I thought my job was to pour into them. It was. But I didn’t expect them to pour back into me.

Here’s the thing: this doesn’t happen by accident. You must be intentional. You have to see every person as someone who has value to share, regardless of their title or years of experience. You have to be willing to be sharpened by people you’re supposed to be sharpening.

John Oliver is one of the reasons I’m now pursuing coaching and helping others discover their purpose. The guy who started as my mentee is now part of my inner circle.

Who in your life might have wisdom you’ve been too proud to receive? Who’s younger, less experienced, but maybe sees something you can’t?

Your next mentor might be half your age.

Be intentional enough to find them and humble enough to listen.

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A couple of months ago, Susanna and I traveled to visit the Oliver family. I had the chance to speak to classes at Harding University, where John’s dad, Mike, is a professor.

Mike, Susanna, me, John, his wife Maribeth, and his brother Joe, who also came through the rotational program.

If you want to know more about John’s work, here’s a great email course he wrote on living a healthy lifestyle. Just in time for 2026: Healthy Habits Accelerator

1. A New Kind of Diversity