This may or may not turn into a regular thing. It might even make a damn good podcast someday. But for now, it’s showing up as a Friday ritual—a little series about what happens when you talk to an old friend about life, aging, grey hairs, and the kind of wisdom you only earn by sticking around long enough to cringe at your own past selves.
It’s not nostalgia. It’s not advice.
It’s perspective—with a little geezer sparkle.
Thems the breaks for we designer fakes
We need to concentrate on more than meets the eye
- Placebo, “Twenty Years”
It was May 2001, SoCal. I was on the loading dock at the Glendale Galleria, sweating my ass off while offloading the very first shipment for one of the first-ever Apple Retail Stores.
My uniform back then? A tank top and a cardigan. The tank was for the heat. The cardigan was for cover. Not fashion—protection.
Underneath? Ink. A fair amount of it. And back then, tattoos weren’t the norm they are today. Especially not in a corporate retail rollout backed by one of the most closely watched brands in the world. So I hid them. Not out of fear of being fired. Out of fear of being seen.
What the cardigan couldn’t hide was the sweat—physical and emotional. I was afraid to take it off, not because I thought anyone would say something, but because I wasn’t ready to show that side of myself. I didn’t know yet if it would be okay.
Turns out, no one cared. I wasn’t the only one. And I wasn’t the only one sweating through the pressure to look like someone I wasn’t.
That cardigan stayed with me longer than it should have—figuratively, at least.
Fast forward to yesterday. I had one of those calls that stays with you. A friend I hadn’t spoken to in years. Both of us, let’s say, of a certain age. Both of us with war stories from the trenches—iconic moments, big wins, wild teams, wilder org charts.
But we didn’t go down memory lane. Not once. We stayed right here, in the now. Two people talking about what it means to be—not just to work.
We talked about working identity. Or more specifically: what’s left when the working part drops out.
It’s that thing that happens when you’ve been around the corporate block a few times. Built a name. Worn the title. Then—poof. You’re out. Maybe you left. Maybe they made the decision for you. Doesn’t matter. Either way, it’s disorienting.
First comes the relief. Clean break. Door closed. You tell yourself it’s fine. Hell, maybe it is.
But then comes the quiet, more unsettling question:
Now who the hell am I?
For me, that reckoning came after I left Apple. I had tied so much of my credibility—my proof of “I’m good at this”—to that logo. Apple was the shorthand. The status. The signal that I belonged in the room.
And when I was no longer wearing the brand? I had to ask:
Was it me, or was it just really good branding?
The good news: it was me.
The bad news: it took way too long to realize that.
That’s the trap. You leave one big job, and the panic sets in. So you latch onto the next one. Learn the language. Swallow the values deck. Shape-shift just enough to fit in. You adapt—until you forget what parts were yours to begin with.
Here’s what I’ve learned:
The more times you leave, the better you get at arriving.
You stop giving away pieces of yourself in exchange for the illusion of security. You hold on to what matters. You stop confusing flexibility with erasure.
Call it age. Call it mileage. Call it the “I don’t have time to pretend anymore” phase. But I’ve stopped apologizing for how I show up. I’ve always been unapologetic in my personal life. But work? That was the last place I edited myself.
Not anymore.
Because when you realize your point of view—your real one—has value, you stop outsourcing your voice. You stop trying to match tone, and start setting it. You stop being the message carrier. You become the damn message.
These days, I live in upstate New York. The rural part, not the curated-for-Instagram kind. And here, no one really asks what I do. Maybe it’s geography. Maybe it’s because I don’t ask them first. Maybe it’s just peace.
But every now and then, someone from the city will ask.
And in that moment, I get to decide.
I could say “consultant.” Or “semi-retired.”
Or I could say: I’m writing a book. I’m building a bathroom in my barn.
Those two? They’re mine. No brand required. No title needed. And that—right there—is the whole point.
Your identity isn’t your LinkedIn headline.
Your worth isn’t tied to a logo.
And the real work—the late-career, no-bullshit, take-your-power-back work—is figuring out who you are without the lanyard.
Because eventually, we all step back. Slow down. Exit.
And when that moment comes, you better know who’s left when the title fades.
If you don’t?
You weren’t working the job.
The job was working you.
Now go check out the song + video: Twenty Years, Placebo (2004