POST 6: Did I Lose Him?

I used to be ahead of the curve.

Not in a polished, LinkedIn approved kind of way. But in the scrappy, half wild kind of way that only kids who once sold weed out of dorm rooms understand.

I quit dealing and turned that same skillset into a real estate license. Same hustle. Same math. Cleaner margins. By my late 20s I was selling houses during the day, rock climbing after work, and finishing a master’s in GIS online because I believed in stacking skills, not hours.

I got fired a week before my 401k match would’ve hit. But I was told I didn’t have to repay my tuition, so I took it as a win. Laughed it off. Moved on.

Then I got hired again. Then fired again. A week before probation ended. My boss never said it out loud, but I knew she saw something in me she couldn’t control. The day before, I bought a new car. Because I’d totaled the old one driving to that same office. Timing, huh.

It was the same office that once gave me a $10 Starbucks gift card after I interned unpaid all semester. And somehow, I still came back. Still believed the ladder led somewhere.

That job gave me a lot, though. It gave me Todd Hammond. Best climber I’ve ever met. Most emotionally stable person I know. Guy who wears shoes until they fall off and never brags about a single one of his 8b+ ascents.

Anyway. That job didn’t last either. Neither did the startup after it. Seven months into Nearmap, they cut me loose. That’s when I left. Abroad. No more cubicles. No more performance reviews. No more pretending I wasn’t too much for the room.

So did I lose that go getter?

Yeah. I think I buried him somewhere in the wreckage of the second firing. Right around the time the second engine swap failed and I learned how easily an “almost” can cost you everything.

But something else got born too. Something slower. Less heroic. More honest.

I still don’t know what I do. But I know what I won’t do again. And maybe that’s enough for now.