Who Are You Now?

The momentum you spent twenty years building suddenly disappears—and there’s no next thing lined up.

At some point, it happens.

The gig ends. The career slows down. The momentum you spent twenty years building suddenly disappears—and there’s no next thing lined up.

And you’re left staring into the middle distance thinking: Now what the hell am I supposed to do?

It’s not just about money. It’s about identity.

Because when the job goes away, something else goes with it—your sense of worth, your usefulness, your confidence. That feeling of I know who I am and what I do.

And when that disappears, it’s hard not to spiral.

That’s what Joe and I talked about in Season 2: Ep 3 of The Man in the Middle Show—the quiet, identity-level crisis that comes with career change in midlife.

He told a story about a guy he was coaching—a high-achieving, high-earning guy who had just lost his job. Laid off. No warning. No plan. And suddenly, this man who’d spent years defining himself by his role and his resume was sitting across from Joe, eyes wide and hollow, asking the question:

“What if I’m just done? What if I already did the best thing I’ll ever do?”

If that line hits a nerve, you’re not alone.

The culture doesn’t give men many tools for this part.

We’re taught to produce, perform, provide. And if you’re doing all three, you're fine. But what happens when one of those pieces disappears? What happens when the career engine stalls—and you’re left trying to figure out who the hell you are without it?

Here’s the mistake a lot of us make: we try to discipline our way through the confusion. We start grinding. Pushing. Rebuilding. Hustling.

Because sitting still feels too much like failure.

But here’s what Joe said that stuck with me: Alignment comes before discipline.

It’s not about working harder. It’s about getting honest enough to ask, "Am I still supposed to be doing this?"

That’s the scarier question. But it’s the one that leads somewhere real.

For Joe, that answer showed up in a weird, unexpected way: endurance sports.

He went from lifting weights and chasing definition to running triathlons and discovering a different kind of strength. One that wasn’t about image—it was about resilience, grit, and pushing his own edge in a way that felt expansive.

He didn’t just find a sport. He found a new identity.

We all need that. A “triathlon” of some kind—something that makes us feel alive again, even if we look stupid doing it at first.

When I stepped away from stand-up, I didn’t know who I was anymore.

I’d spent over a decade getting good at something that I thought was going to be the centerpiece of my life. Then I realized I was good at it, but I wasn’t called to it anymore.

Letting it go wasn’t just scary—it felt like betrayal. Like I was giving up on a dream. Like I was wasting all that time and effort and sacrifice.

But when I zoomed out, I saw the bigger truth: that dream was the bridge that got me to the next chapter. And the next chapter was calling louder than the applause.

If you’re in the middle of one of those transitions right now, here’s what I’ll say:

You’re not broken. You’re just in between identities.

You’re not falling behind. You’re reorienting.

You’re not lazy or lost. You’re listening—and that’s something most people never even try to do.

Ask yourself:

If I stopped doing what I’m good at, what would I start doing that feels more like me?

That’s where the alignment lives.

Thanks for reading.

If you’re walking through your own professional shakeup, or you know someone who is, pass this along. Let them know they’re not alone—and that starting over doesn’t mean starting from scratch.

It might just mean you’re finally doing it right.

—Kevin