The Ghost of Who You Thought You’d Be

What did you want to be before the world told you to be practical?

What did you want to be before the world told you to be practical?

Before the student loans, before the mortgage, before the job that made sense on paper—what lit you up?

If you’re like most men in midlife, you’ve probably forgotten. Not completely. It’s there in the background—fuzzy, quiet, easy to ignore. But every once in a while, it taps you on the shoulder.

You’re driving, or shaving, or scrolling through someone else’s highlight reel, and there it is:

The version of you that didn’t compromise so much.

It’s not about fame or money or chasing some lost fantasy. It’s about meaning. Expression. The part of you that still wants to feel alive in your own skin.

In Season 2: Ep 2 of Man in the Middle, Joe and I talked about those early dreams—the ones we chase, the ones we bury, and the ones that start whispering louder as we get older.

As a kid, Joe was obsessed with SNL. Memorized sketches. Studied comedians. Rehearsed in front of mirrors. That creative urge didn’t go away—it just morphed into something new: leadership, coaching, and helping other men find their voice.

For me, the spark was always about connection. Making people feel seen. Saying the thing everyone else was too scared to say. I’ve used that instinct in everything I’ve built since.

And here’s the thing—we don’t outgrow those early passions. We just get busy. We build lives around other people’s expectations. We trade creative energy for stability, and call it maturity.

But those parts of us don’t die. They wait.

Carl Jung once said, “Nothing has a stronger influence psychologically on their children than the unlived life of the parent.”

We don’t just carry our own dreams—we carry the silence of theirs.

So when your dad told you to “get a real job,” or when your mom got nervous about your ambitions, or when no one showed up to encourage the weird, wild thing you wanted to do—you adapted. You got realistic. You put the dream in a drawer.

And now it’s showing back up. Maybe not as a career, but as a craving. A restlessness. A need to create something that isn’t just another invoice or meeting or deadline.

Here’s what I know now:

Regret isn’t weakness. It’s information.

It’s your soul flagging something that still matters.

You don’t have to “go back” and do it all over again. You don’t need a radical reinvention. But you do need to listen.

That dream? That version of you that felt fully expressed, curious, reckless, and alive? He’s not gone. He’s just been waiting for you to come back and pick up the thread.

You’re not too old.
You’re too alive to keep lying to yourself.

—Kevin