The Best Cockpit Companions

Flying with a good pilot makes for better flying.

Pilots Courtney Crain and Dick Karl
Pilot Courtney Crain hams it up after landing in KOAK.Courtesy Dick Karl

"Stop, you’re getting your head down. Tell the pilot monitoring what you need. You seem to want to do everything by yourself.” So said Capt. Andy when I was the pilot flying early in my tenure on the Cessna Citation CJ3 at JetSuite. He was right. Up until then, all my flying had been single pilot, and I wasn’t eager to share the fun with anybody else. The truth is, I didn’t know how.

Soon, however, I came to enjoy, even relish, the shared cockpit. No doubt some of this pleasure was the consequence of the circumstances in which I had landed. Almost all my colleagues at this Part 135 company were amiable and easy going. They were also much better pilots than I was.

When I bid a reluctant farewell to charter flying, I sought to console myself with a new airplane. So my wife and I sold our trusty Piper Cheyenne and bought a Beechcraft Premier. What a consolation. Though the airplane’s maintenance ­horrors ultimately chastened me, I found the single-pilot-jet thing to be eerie at first. One day, I looked up to find myself alone in the airplane, gliding along at Flight Level 410 at a ­groundspeed of 560 knots. By myself. I lay the oxygen mask on my lap.

As many readers know well, the Premier was done in by a bird strike (a pelican), and we subsequently bought a Cessna Citation CJ1. Though slower and less fancy, this airplane has proved to be perfect for us. With 1,000-plus hours in the CJ3, the cockpit layout and sight picture are familiar. I became immediately comfortable flying this smaller jet. Very lucky man, I know, I know.

Returning to single-pilot ­operations, I’ve found it sometimes difficult to maintain the discipline that seemed so natural when flying with somebody else. I have overlooked some obvious checklist items, reminding me that checklists, when performed by two individuals, are much more effective than when only one pilot reads from a plastic card he’s seen a thousand times.

When an eye condition robbed me of my medical and grounded me, I sought to hire pilots to get me back up in the air. Here was a chance, albeit a forced one, to fly with professionals. I found myself a long way from home in Tampa, Florida, when it became clear I was not fit to fly. What could I do?

I could call Courtney, that’s what. Courtney and I flew many trips together in the 135 world. Qualified in the CE 525, she was one of my favorite captains. Generous, fun, ­possessed of a great sense of humor and a first-class pilot, we’d kept in touch as she moved up the food chain to Atlas on the Boeing 767 and now to UPS. She was home in Long Beach, California, and said, “Sure.”

We had a fun reunion at Burbank’s Kaiser Air. I had told my passenger friends and wife that I had hired a safety pilot. Imagine their ­surprise when Courtney showed up with a backpack, water bottle and a filed flight plan. She’s one of those people who lights the place up.

Our flight was too short—just an hour. We used the old company callouts and briefing sequences. Otherwise, we spent the trip ­reminiscing, laughing and catching up—when not occupied with ­cockpit duties, of course. I reimbursed her for her time and, sadly, put her on Southwest Airlines back to KBUR. After the engine covers were on, I realized how much I had missed flying with a professional. This is especially true in unfamiliar, busy airspace (I’m pretty much an East Coast pilot) and especially true with this pilot.

After two days with friends in Sausalito, California, we were scheduled to fly to Bozeman, Montana, to pick up my brother and his wife and bring them to Tampa. I needed help. I looked through some ­contract-pilot sites but couldn’t seem to raise any interest in a pop-up trip from coast to coast in a CJ1. I lamented to two friends about this predicament. Here’s the thing about aviators: They will help you out.

My friend Rob, senior pilot at Southwest, canceled a paying trip to be ready to fling himself across the country from Orlando, Florida, to join me in the cockpit. Seriously.

Rob is also my favorite cockpit ­companion. He’s a good friend and a highly knowledgeable pro, and he has a generous way of living.

But wait—Tom, a pilot friend from Tampa who admits to being an airplane nut, had already gotten space on his airline (he’s a captain at American Airlines) to fly to Oakland, California. He’d fly us home. We picked him up at the terminal and took off for Montana 30 minutes later. On the final leg home from Tulsa, Oklahoma, to Tampa, we worked our way through a line of thunderstorms at Flight Level 390. As we inched toward the weather, I was grateful to have this Aerostar-owning, flown-everything, experienced pilot next to me. He didn’t tell me it was his birthday until after we landed.

Two weeks later, I needed one more assist to get to New Hampshire. I ­contacted Laura, who owns a 135 operation in Tampa with her husband. They operate a CitationJet. We met for coffee, and I liked her immediately. We made plans for the following week.

Due to a series of improbable but fortuitous events, I had my medical back before the flight. Nevertheless, I reasoned that I had already contracted Laura to fly, and I was looking forward to learning more from somebody who operates a similar jet all the time.

Fabulous fun is what it was. Laura, who flies with lots of ­owner-pilots, was very complementary, and I learned a lot from her. We left Tampa midmorning, stopped in Georgetown, Delaware, to pick up two grandsons and flew to Lebanon in time for Laura to catch a Cape Air flight to Boston and Delta back home that same night.

Since then, I’ve been getting around by myself, but I miss that reassuring presence of a pro next to me. Especially these really nice ones. There is no doubt that the ­environment has much to do with my affection. Had I been tasked to perform earthbound duties with similar people, would I have anywhere near as much fun? Is it the fact that we’re in the air, hurtling along in comfort with the sky as window dressing, that makes the two-pilot cockpit so magical? Or is it that the sky attracts a certain kind of person—the kind that would be fun to do anything with?