I Just Found Out I’m a Great-Grandfather Mentor

I hope you’ll forgive the clickbait-ish title, because I’m genuinely excited to share this.

A few days ago, I (Mr. Bill Berry) received a message from one of my earliest students, and it made me smile the biggest of smiles.

Years ago, he'd been stuck in a soul-crushing office job. The pay was fine, the work was secure, but every day felt like it was draining the life out of him.

One day he reached out and said, “I’m thinking about quitting my job and going to India for a month. What do you think?”

I didn’t tell him what to do. Instead, I asked him a question.

“Imagine you’re 80 years old. You’re lying in a hospital bed looking back on your life. Which version of your future self do you think will be happier? The one who says, ‘I’m so glad I stayed in that safe office job,’ or the one who says, ‘I’m so glad I dropped everything and went to India and had an adventure’?”

He didn’t hesitate.

“I’m going to India.”

That one decision changed the trajectory of his life.

What began as a one-month trip became the first of countless adventures. He spent seasons in Norway working aboard an authentic Viking ship, taking it out under sail. He flew to Australia planning to stay only a few days, wandered down to the docks, signed onto a three-masted tall ship, and spent months sailing the coast.

Along the way he discovered confidence he never knew he had.

Eventually he started his own electrical engineering company, designing and building custom equipment for startups, artists, and creative businesses. He’s invented remarkable things, built a thriving career on his own terms, and genuinely made the world a better place.

I’ve always been proud of him.

But that’s only half the story.

A few years ago, he told me about someone he met in a coffee shop. This person was in a situation that sounded strangely familiar: trapped in a job they didn’t enjoy while secretly pouring their heart into a side business making handcrafted birdhouses.

My student saw a younger version of himself.

So he did something beautiful.

He encouraged this stranger the same way I had encouraged him years earlier. He shared stories. He challenged limiting beliefs. He asked questions. He passed along the same ideas that had once transformed his own life.

The stranger listened.

Today, that person has built an incredibly successful business. From what I hear, he and his wife now spend three months every year traveling the world. Then they come home, focus on the business for nine months, and head off on another adventure.

They’re living a life they intentionally designed.

I already knew about this “second-generation” student.

What I didn’t know was that this second-generation student had gone on to mentor someone else.

That’s why I was so excited to receive this message and screenshot from my original student. In it, the second-generation student is telling my first-generation student that he's passed it on and inspired yet another person to pursue a bigger life. Which makes my first-generation student a grandfather mentor.

I loved this so much that I asked my student (Mike) if I could share it here with all of you, and he said he'd ask his student (Matt) if that was cool. This is what Matt said:

Hi Matt, I'm so pleased to meet you. And thank you, Mike, for believing in your own dreams, and then passing on the method to make it possible for others like Matt, and now Matt's student, to do it too.

I never could have imagined this all those years ago, that one day I'd become a great-grandfather-mentor, but here we are. Not because I directly taught Matt; I've never had the pleasure of meeting him. But because one conversation led to another. One person believed in someone else, who believed in someone else, who believed in someone else.

Like ripples spreading across a pond, the methodology kept traveling long after the original conversations had ended.

It’s easy to think our influence ends with the people standing directly in front of us.

It doesn’t.

Every time you help someone become a little braver, a little kinder, or a little more willing to pursue the life they really want, there’s a chance they’ll pass that gift on to someone else.

And while we'll probably never know the extent, or how far those ripples travel.

Never doubt that they do...