Weekend Warrior Recap
Back Behind the Wheel!
I’ve been off the rideshare grid for about three months. I did a few private runs here and there, but slowly easing back into driving and gig work. My father passed away in June, and for a while the only place I wanted to be was home with family.
2026 has been a bruise-you-from-every-side kind of year: adjusting to a second child, moving to save on rent, getting a layoff notice, hunting and interviewing for a new job, starting and training at that job—and then losing my dad.
I also poured years into growing my YouTube channel and had to let go of sponsorships I’d worked hard for simply because I couldn’t carry the extra load. I won’t sugarcoat it—all of these loses have been demoralizing.
The good news: it’s only the end of August, so hopefully the worst of this year is behind me. There’s still runway left in 2026 to turn things around.
To pull myself out of the rut, I got back on the road within two weeks after my father’s passing. Not a ton of driving, but enough to make progress each and every week. And this past weekend I accepted my first rideshare trip in months. That first ping—after all the silence—felt like getting a monkey off my back. I immediately felt at home again, connecting with riders while moving through familiar streets.
I woke at 2am for a rescheduled private ride to the Philly Airport. The passengers were first-timers—pleasant, easygoing—and the trip was smooth except for a wild thunderstorm that turned parts of the drive into a slalom of puddles and debris. After dropping them, I headed south toward Delaware, keeping both rideshare apps on and waiting to cherry-pick a good request. It was only when I hit Wilmington that a trip I actually wanted finally came through.
The first rideshare trip was a pickup to a small county airport. And I was shocked when the rider came out of her home with zero luggage, not even a small carry-on.
I joked as she got into my Tesla, “Flying without luggage?” and she laughed: “Oh no, I’m not traveling—I’m headed to work. But I wish I was.”
So I asked the inevitable question: “If you could fly anywhere right now, where would it be?”
“Trinidad and Tobago—on the beach,” she said without hesitation.
We spent the whole ride swapping dream-destinations and daydreams about being somewhere warmer and simpler than the workday ahead. Those small conversations—two strangers trading where-they’d-rather-be lists—are exactly why I drive. It’s less about the fares and more about the human connection: the brief pause from life’s grind, my father’s passing—just the chance to laugh about shared wishes, the little solace of imagining a beach.
I did a handful more runs and got home in time for breakfast with my wife and kids. The weekend closed out at just over $150 including that private airport run. Small haul, but satisfying.
One caveat: I think I might have sped through a stretch that recently got a speed camera. So there’s a chance all that Sunday 2am wakeup effort could be eaten by a ticket. Classic! 🤦♂️
Still—after months away, the road felt right again. The pandemic of sorrow and stress hasn’t vanished, but the Tesla’s tires are warm. I’m easing back into the rhythm, one weekend at a time, and looking forward to more rides, more conversations, and a little more normalcy.
