Staff Software Engineer


I’m in a window seat, at 36,000 feet, and just finished up my free mini bottle of buffalo trace. Years ago, this was my happy place. Flying somewhere, leaving some place, being treated like someone special because I spent so much damn time and dollars for the right to sit on an airplane as it took me from point A to point B.

Sure, I’ve been a United 1K for half a decade at this point. Racked up almost half a million millions flown in the past 6 years. But it was more than that. I was a frequent flier, damnit. I could navigate airports with my eyes closed, could tell you the best seat on every plane in UA’s fleet. Hell, I called United Airlines “UA”, because that showed how much of an insider I was.

Now, we’re several years and one giant global pandemic later. The world’s been turned on its head so many times over the past two and a half years, I can’t even remember if it’s currently upside-down or rightside-up. And here I am, sitting in seat 10F (have booked 10D, don’t ask questions), having consumed my in-flight freebies, and …… it’s not the same.


Flying was my personality. It was my schtick. “I spent a night in the Singapore airport working, and downing an entire bottle of champagne while sitting alone in the business class lounge” was not only a true statement, but a point of pride. It was how I introduced myself. It was my dating app profile. “I took a spring break in Hong Kong just to eat dumplings” was true. And I fucking loved that spring break!

And here I am, having flown SFO-NYC two weekends in a row for two different weddings. The travel used to be part of the fun. Enjoying the journey as much as the destination. You know the cliches. But, at least for a lot of the travel I’ve done this year, that’s been gone. Few upgrades. Chaos in airports. Ticket prices doubling verses the baselines I had memorized. Seatmates not wearing masks. Middle seats having people in them. My favorite flight times no longer on the schedule.

The spontaneity is gone. The absurd is gone. Chasing the sun in a lie-flat seat is… gone. The last trip I had scheduled, before the world shut down, was supposed to be vacationing in Sicily with my mom. Of course, I was going to get to Italy from San Francisco via Toronto, Mumbai, and Geneva. I loved it. Arbitrage opportunities for earning status, a silly amount of time spent in business class, just being absurd about flying. Saying “sign me up” doesn’t cover it – I didn’t need convincing. I sought it out. And me being me, I consistently found it.

And now… who knows if I can do that again. Remote work makes it harder to just disappear for a conference and say it’s all work (yes, it is all work); now I’m expected to be on Zoom and Slack constantly, even if I’m 9 time zones away and just spent 20 hours in transit. That’s not relaxing. It’s also not conducive to randomly finding Michelin star restaurants in insert city here to walk into for lunch. Besides, half the places I loved to do that in have been off limits until the past few weeks.

To top it all off, for whatever reason I have utterly failed at taking time off the past few years. Yeah, I was bad before. But now? Why take a day off to ski when I can take meetings from the slopes. Why take an extra day when going to a conference when I can be home in time to open my laptop and call into sprint planning? Seriously, why???

So, to tie it all into the title that I penned in my mind before opening my laptop, I think I’m nostalgic for a life I had. I’m fighting internally against the idea of giving up on being the jetsetter, the mile-chaser, the guy who flew a bunch and fucking loved it. Because I loved it. I want to find a way to recapture that love of showing up to SFO hours early for a transcon to get a free meal and drink in the lounge, or spending a weekday going out of my way to LAX or IAH to secure double-digit hours in a business class seat upgraded with PlusPoints. That shit was so fucking fun!

Do I know how I’m going to go back to it? No. But I’m working on it.