The Man with the Dog: My Greatest Fear in Plain Sight

Most of the time when I write, it’s to celebrate a milestone or share a travel story or tip or to highlight a destination.

This post is different. It’s raw. It’s personal. It’s something I’ve carried privately for a long time—but I think it’s time to say it out loud. Not because I want attention, but because I know I’m not the only one carrying this fear. And maybe by naming mine, you’ll feel a little less alone with yours. So here goes....

I met him in Hawaii several months ago.

Not with words.Not even with eye contact.But at a soul level. Just… presence.

He was sitting on the sidewalk near a store called Jungle Love, tucked in next to a cardboard box, a soda can, and a stuffed animal. His dog sat loyally beside him—alert, calm, watching. That dog didn’t need a leash. His heart was tied to the man beside him.

I couldn’t stop looking. And I haven’t been able to forget him since.

I saw more than a man that day.I saw my deepest fear.

Because here's the truth I never say out loud:

When I think about one day walking away from my J-O-B to work solely for myself—the salary, the structure, the insurance, the safety net—I don’t just fear failure.I fear ending up like him.Broke. Homeless. Forgotten. Sharing dog food with my boys, Barry and Blade somewhere on Mozart Street.

That image haunts me—not because it’s likely, but because it’s possible. And because in some twisted way, part of me believes I’d deserve it for wanting more.

Wanting freedom.Wanting joy.Wanting ownership of my life.

But the more I sit with this fear, the more I realize something that’s shifting everything:

That man isn’t my future.He’s a mirror.A wake-up call.Not about what could happen if I leap……but about what will happen if I don’t.

If I keep living inside other people’s expectations.If I keep shrinking to fit roles I’ve outgrown.If I keep choosing routine over risk, and comfort over calling.

Because the version of me that hides… delays… minimizes himself for the sake of stability...

That’s not security.That’s spiritual homelessness.

I don’t know that man’s story.I don’t know how he got there or what he’s surviving through.But I do know my story isn’t finished.And if I don’t write it—on my terms—then the fear wins.

We all have a version of that man.A moment that haunts us.A fear we try to outrun.

But what if we stopped running?

What if we stared it down……named it……and then made a different choice?

If you’re reading this, and you’ve been stuck at your own edge…Afraid to leave.Afraid to leap.Afraid to live more honestly…

I see you.And maybe this is your mirror.

Let’s leap anyway.

Because the dogs deserve better.And so do we.