A Musician Turned Pilot Shows It’s Never Too Late to Find a New Career

“It’s Never Too Late” is a series that tells the stories of people who decide to pursue their dreams on their own terms.

Live music was no more. Patrick Milando could draw no other conclusion. But maybe he could pivot.

It was a summer day in 2020, a peak of the coronavirus pandemic, and Mr. Milando, a French horn player, had been driving through a locked-down, emptied-out Times Square. Then 67, he had spent nearly a half-century as a professional musician, from the Metropolitan Opera to over a dozen years with “The Lion King.” Now that musical, along with so much else, had shuttered. At an age when his peers were wrapping up their work, Mr. Milando found himself pondering a new way to pay the bills — 5,000 feet above his old way.

Sometimes we leap happily to an all-new life. Sometimes we leap happily with a push.

Mr. Milando had begun flying single-engine planes before the pandemic, but purely as a hobby. (He had logged around 300 hours of flight time.) Now, he wondered, could he actually become a professional pilot? He was too old to fly for the major airlines (the cutoff is 65), but there was no age limit on teaching others to fly.

Mr. Milando found a small flight school in New Jersey and set out to earn his commercial pilot certificate. The other pilots there tended to be decades younger, and not once did he spot a fellow French hornist. (Most seemed to work in computers, he observed.) But he felt at home; flying unlocked something in him.

“There’s a freedom, an autonomy. You’re the master of your own destiny,” he said.

Today Mr. Milando, 71, has two careers — it turns out the death of live music had been greatly exaggerated. He splits his time between the orchestra pit and the friendly skies, where he teaches budding pilots like he himself once was. (The following interview has been edited and condensed.)

How did you get interested in flying?

Being a musician, I did a lot of traveling. I was very intrigued by the flying aspect. I got a flight simulator game for fun, when my kids were young. You’d hear me in the basement yelling, “Pull up, pull up!” When I turned 60, my wife got me flying lessons. From there, I got my private pilot’s license.

What do you like about flying?

It’s very serene. One of the most enjoyable times is when you’re going through the clouds, and you’re relying on your instruments training, then all of a sudden you’re above the clouds and you have this beautiful panorama in front of you.

It’s a rush. The first time you do it, it’s life-changing. Life-changing and life-affirming.

It seems a tad riskier than playing the horn. Was it ever scary?

The scariest was landing for the first time. I remember I had an opera down in West Palm Beach, and I’m up there with my instructor at 1,500 feet, looking down at the tarmac, thinking, Well, I just have to land this plane. Afterward, I felt like I was going to cry. It was just so intense, and amazing.

What prompted you to think about flying professionally?

When the pandemic came, all of us musicians were like, “Oh my God, what are we going to do?” The prevailing feeling was that music was going to stop; Broadway was never going to come back.

I remember driving one day through Times Square and seeing everything boarded up. It was really scary and I thought, OK, let’s just try career No. 2. I’m not one to sit around and do nothing.

So how did you make it happen?

I found this small flight school in New Jersey, called Sky Training, and got my commercial rating. Then I flew to Minnesota later that summer to get my certified instructor’s rating, so I could teach other people to fly. I also picked up a seaplane rating, just for the heck of it. Eventually I flew a seaplane over Lake Como in Italy and was waving down to — who is it that lives there? George Clooney?

Anyway now I teach people to fly everything from a single-engine Cessna to a multi-engine Piper.

Are there similarities between music and flying?

My success as a musician has always come when I’m totally focused in the moment. When you put aside all the extraneous things going on around you. That’s sort of what you have to do when you’re flying an airplane.

As a teacher, I’ve had a student freeze 100 feet from the runway. I had to push his hands off the controls and take them. He was in a mental freeze, couldn’t get out of it. You always have to be in the moment.

How often do you fly now?

That’s the tricky part because I’m responsible for eight shows a week at “The Lion King.” Monday is dark, so I usually pack the day with students, and just keeping current on flying different airplanes. Then I’ll usually hire someone to play for me another day that week, and teach more people. So I end up flying maybe 15 hours a week.

Any advice for people who are interested in making a change like this, but worry they’re too old to learn something new?

I say go for it, absolutely go for it. There’s no reason not to.

Are you done making big changes?

I’m like a shark, I gotta keep moving. I’ve run eight marathons; I like learning languages. Now I’m kind of wondering about an Airline Transport Pilot certificate, the A.T.P., so I could start flying people down to the Caribbean. It’s pretty much the final step in aviation.

Each time I say I’m done, my kids say, “Yeah, I’ve heard that before.” So I guess I’m going to get that A.T.P.