FLYING Magazine

This spring, I celebrated three major milestones: 10 years at my current “airline,” 20 years as an airline pilot, and 30 years since starting flight lessons. I’ve been a pilot for nearly three-quarters of my life, and it’s hard to remember a time when the surly bonds could not be slipped.

I recently caught up my logbook in preparation for a New Zealand PPL validation, and I’m closing in on 16,000 hours. The country’s authorities also wanted to know my solo time—e.g., sole occupant of the aircraft. The number was surprisingly small, most from way back when I was a Part 135 freight dog. These days, all my work flying is multipilot, but even when puttering around in my Stinson 108, I’m usually accompanied by my wife or friends. I don’t mind flying alone, per say, but I do find it more rewarding when there’s someone with whom to share the experience.

In two decades at the airlines, I’ve come to appreciate that those I fly with really are one of the best parts of the job. Over the years, I’ve shared the flight deck with hundreds of pilots and enjoyed flying with almost all of them. Going through my logbook, I see so many familiar names—and some are still good friends. This is a small industry, and I have chance encounters with past colleagues all the time—in airplanes and airports, obviously, but also in crew vans and layover hotels and pilot-frequented bars, like Darwin’s Theory in Anchorage, Alaska, or Moose’s Saloon in Kalispell, Montana.

My last two airlines, Horizon Air and Compass, were small regional carriers, and it was pretty common to fly with the same person multiple times. This didn’t happen much during my first eight years with my current employer as we’re a huge airline of 17,000 pilots, and over that time I flew three aircraft types out of three large bases. Once I bid to the fairly small Seattle 737 base, though, I started occasionally flying with the same first officers, and it was nice to experience that familiar, small-airline vibe once again.

READ MORE: Exploring New Zealand’s Grand Islands by Air

One thing I haven’t done, until recently, is buddy-bid with anyone. This is the practice of coordinating your schedule bidding strategy with a pilot in your base to fly as many trips together as possible.

My good friend Brad Phillips, who I’ve written about here, buddy-bid the majority of his 11 years at Horizon Air with just two captains. I’ve also written about Joe and Margrit Fahan, a married couple at my airline who, prior to their joint retirement, buddy-bid international trips on the Airbus A330 together. Over the years, I’ve had trips where I really clicked with my counterpart and probably should have broached the idea of buddy-bidding but always figured that variety is the spice of life. Besides, doing so with any degree of success demands a good bit of seniority out of both parties, and until recently this is something I usually lacked.

But then in summer 2022, I flew with Steve Masek, and we went salmon fishing in Anchorage and had beers at Darwin’s and got along famously. We bid several more agreeable trips together, our wives met and gelled well, and Steve and Daniela gamely helped Dawn and I lay down 3,000 feet of PEX tubing the weekend before our hangar floor was poured. But then Masek got himself awarded a B737 captain slot, far below me on the list in that dark, dank corner where poor junior slobs are forced into reserve, red-eyes, and four-leg days. It was a dumb thing to do, but I’m thrilled for our junior FOs because Masek is a super guy and an excellent pilot.

Before his upgrade last fall, we buddy-bid one last long Anchorage overnight. We wet our lines in Ship Creek on a midnight rising tide, chomped cigars, and quaffed Woodford Reserve in the moonlight—and, alas, the salmon treated us to not even one solitary nibble.

READ MORE: Part 2: Exploring New Zealand’s Grand Islands by Air

By then I had already found Masek’s replacement, Heather Griffin. We flew a three-day trip together last July and quickly realized that we were going to be fast friends. Heather got her start flying skydivers and is a licensed skydiver herself, as am I. Griffin also flies paragliders, which is a goal of mine. She snowboards and I ski, we both sail, and we both ride dirt bikes.

On the last day of our trip, she realized that I’m the guy who writes for FLYING and used to live on a sailboat and spent years cruising the Caribbean, and she told me that she actually decided to pursue an airline career after her dad (also a pilot) showed her my columns as evidence that she could fly for a stuffy old airline and still live an unconventional, adventurous life. Aw, hell—with me, flattery will get you everywhere. Instant BFF.

Griffin and I were planning a flying, camping, and dirt-biking trip to Tieton State Airport (4S6) in the Cascades of Washington state for a few weeks hence, and she and her husband, Kevin, accepted our invitation to join. We had a great weekend, flying the Stinson at sunrise and sunset, riding Bethel Ridge in the mornings, splashing in Rimrock Lake during the sweltering afternoons, and talking around the campfire while millions of bright stars wheeled overhead. Dawn got to know Heather and liked her a lot.

Meanwhile, I developed a man-crush on Kevin, who’s as cool as his wife: an air ambulance pilot with a bunch of tailwheel time, a badass dirt bike rider, and a great storyteller with a wicked sense of humor and a colorful past as a Coast Guard flight mechanic, commercial fisherman, and Alaskan surf shop operator.

READ MORE: Pilot Mental Health Remains the Last Taboo in Aviation

With the spouses properly introduced, Griffin and I started buddy-bidding. When the PBS window opens each month, we peruse the bid package and text back and forth, debating the merits of various trips and crafting a common strategy that will fit both of our plans. Sometimes it works; sometimes it doesn’t. When the schedule assignments come out, we dig into the reasons report, figuring out what we did right and where we went wrong. As our trips together approach, we confer again to make layover plans: playing pinball in Raleigh, North Carolina, skydiving in Phoenix, roping up at an Anchorage climbing gym, or skiing at Lake Tahoe.

In cruise, shared interests fuel our conversations, and future adventures are a frequent topic. It didn’t take much to convince Heather and Kevin to join Dawn and I on an 11-day, 11-person dirt bike trip down Baja California in January. Griffin’s dad, Scott Condon, came too—and at 65 turned out to be the best and fastest rider of us all. It was a fantastic time with a wonderful group of friends, and we’re planning another big ride in the Pacific Northwest this summer.

In February, Heather and I got skunked, our buddy-bidding strategy foiled by pilots just senior to us. I flew with a bunch of great folks anyway—several of them brand-new to the airline—and had a lot of fun. March brought better luck. I’m about to fly a five-day trip with Griffin that includes a long Cozumel layover, and later on we have an easy four-day with 26 hours in Cabo San Lucas, where Dawn and Kevin will join us.

Most days, this is a really good job, and I frequently wonder at my good fortune. And then, when I thought my work life couldn’t get much better, I gained a good friend to fly with—and it did!

This column first appeared in the May 2024/Issue 948 of FLYING’s print edition.

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