By Steve Segner
As the owners of a small boutique hotel, Connie and I have had the pleasure of meeting people from all walks of life, including governors and Supreme Court justices. Over the years, we have formed close relationships with many of our guests, making it difficult for us to travel without missing a visit from our now friends. One of our guests, asked me to write a note to their son, Jack, who will be a junior next year. My comments to Jack and I think young people starting their own journey.
Dear Jack,
It was great to see you last week during your parents’ biennial visit. I’m glad we were able to arrange for you to have your own room—this wasn’t just a matter of luck or logistics. It was my quiet way of acknowledging something important: you’re no longer a child.
I’ve known you since you were about seven, and even then, you carried yourself with a quiet maturity that stood out. Your parents have always spoken to you with honesty and included you in real conversations—not as a child to be managed, but as a young person to be heard. That kind of upbringing is rare, and it gives you something most people don’t get until much later—if ever.
As you grow older, you’ll begin to notice it more: how you often see things others miss, how your instincts guide you, how your questions go a layer deeper. It’s not that you’re better than anyone else—it’s that you’ve been equipped differently.
That brings me to the heart of what I want to say:
Don’t let the world convince you to stop being Jack.
Don’t trade authenticity for approval.
There’s a strong pull—especially at your age—to fit in, to smooth your edges, to follow the crowd. Resist it. You weren’t built to be average.
Marcus Aurelius, a Roman emperor and one of history’s wisest thinkers, wrote about the importance of living according to your inner compass—your true nature. Jack, that compass is already forming inside you. Trust it.
Yes, listen to advice from people who care about you—but in the end, live by your own direction. You’ll make mistakes (we all do), but let them be your mistakes—not the product of someone else’s idea of who you should be.
Think of life as a long highway, stretching from birth to death. Some people take the freeway—fast, straight, predictable. You and I? We’re backroad people. We take the winding, scenic routes. They may take longer, but they’re filled with detours and discoveries—and they teach us more than any shortcut ever could.
And here’s one last thing to think about:
You are, in many ways, the average of the five people you spend the most time with. Choose those people wisely. They don’t need to be your intellectual equals, but they should share your values. Surround yourself with people who lift you, challenge you, and inspire you to be better.
Jack, you’re already on your way.
Keep walking your path—with curiosity, courage, and kindness.
Warmly,
Your friend,
Steve