What I Learned Flying Airplanes

This is an adaptation of my weekly newsletter, Adventures Big & Small. If you want to receive emails like these, click here to subscribe.

On my 30th birthday, I cried while eating a Whole Foods sushi dinner, by myself, in a basement-level hotel room in one of those upscale exurbs of New York. White Plains, maybe?

It didn’t matter exactly where I was because all that mattered was that I wasn’t home. But more than just being home, I wanted to be headed home…like, philosophically. With my life.

I had spent 6ish years working hard to reach that moment. I was the captain of a charter jet. I had flown helicopters and seaplanes. I’d owned an airplane and run my own instruction business. My resume was solid. Cool, even.

But I didn’t feel cool. I felt lost. Aviation had become a growing checklist of things I didn’t want from my life.

A few years later, after pushing through one too many moments like those and reaching some sort of tipping point, I sat down and actually wrote out that list.

This was during a next phase, when I was commuting from SF to Reno, flying air ambulances week-on-week-off. I remember sitting at the cheap kitchen table in the crew quarters, looking at the fake wood top, pressing my bare feet into the cheap apartment linoleum. This wasn’t working. What would be next?

I decided to write down what airplanes & helicopters had taught me about how I didn’t want to fill my life:

180 nights a year in a shared apartment with strangers
Nonstop travel
Constant risk
Incessant noise
Wearing a headset for 8 hours straight
Seeing beautiful things — mountains, beaches, canyons — that I couldn’t touch from my little bubble in the sky
Airport food
Ubers
The pressure of big money
The FAA…all its rules and checkrides

I’m 37 now. And I’ve gladly let my pilot credentials lapse.

I walked up the hill to my office this morning at 4:45 am and paused for a few deep, grateful breaths under a starry sky fading into twilight. The Pacific wrens were already trilling in the Douglas fir.

Today, my daughter and I will plant more basil in the garden together. Then we’ll let the chickens out and she’ll catch them and we’ll say, “The chickens feel so safe when you hold them gently.”

Before dinner we’ll look for a few early blackberry treats along our dirt lane. We shared the first of the season yesterday.

And tomorrow I’ll sit down to edit photos from a Point Reyes beach session that was way more fun than work. Or maybe just the kind of thing I’m proud to now call “work.”

See you Sunday after next.

–David