The Realities and Rewards of Life as a Pilot with Shane Steinecker – Episode 16

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From the Cockpit to the World: An Inside Look at Life as a Pilot

Ever wondered what really goes on behind that cockpit door? What it takes to log thousands of hours in the sky, captain a Boeing 777 carrying 400 passengers, or land a jet in a narrow mountain valley in Aspen?

On a recent episode of Bon Voyage Besties, host Rachel sat down with Shane Steineckert, a pilot with over 6,500 hours of flight experience across airline, military charter, and private jet operations, to pull back the curtain on life as a pilot. From the road to becoming one, to the realities of scheduling, maintenance delays, and flying over open ocean, this conversation is packed with insight for aviation enthusiasts, aspiring pilots, and nervous flyers alike.

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The Journey to the Cockpit Is Rarely a Straight Line

Shane’s path to becoming a pilot is a masterclass in persistence. Born and raised in Salt Lake City, he first caught the flying bug after his mother took a job with Delta, giving him access to free flights. Watching pilots stride through airports in their uniforms, he was hooked even though he had almost talked himself out of it, convinced he wasn’t smart enough or didn’t have the right credentials.

What followed was anything but easy. Shane enrolled in a flight school in Orlando, took out $80,000 in student loans, and then watched the school shut down overnight with no warning and no refunds. He walked away with nearly no training completed and a mountain of debt. Rather than quit, he took jobs as a Southwest Airlines ticket agent and a ramp agent just to stay close to aviation. Years of rebuilding followed: nights, weekends, new loans, a bridge program, and finally — seven years after most people complete the process in eighteen months — his first flight in a 76-seat regional jet from JFK to Dallas.

“I thought about quitting many, many times,” Shane admits. “But flying was what I loved. It’s the only thing I could see myself doing.”

That determination eventually led him to the pinnacle of his career: captain of a Boeing 777 — one of the largest airliners in the world at 200 feet long and 200 feet wide — flying military charters to nearly every continent. It was the exact plane he had spotted in a wall mural at his very first flight school as a 20-year-old. He got there.

What Life as a Pilot Actually Looks Like Day to Day

One of the biggest misconceptions Shane hears constantly? That pilots fly a set route. “What’s your route?” is the first question out of nearly everyone’s mouth. The reality is far more dynamic. Pilots bid on their schedules monthly, ranking their preferences based on seniority, days off needed, trip lengths, departure times, and the system assigns trips accordingly. The most senior pilots get the prime picks; the newest ones take what’s left.

Shane’s preference? Short trips. A day run to Vegas and back, maybe a two-day trip at most. That flexibility, being home more nights than not, is one of the things he values most about his current role at a domestic airline, especially compared to the international charter work that had him away for ten to fourteen days at a stretch.

“I can still work until noon and be home the entire afternoon to be with my kids,” he says. “That’s huge.”

Still, life as a pilot demands a certain kind of independence. Eating out for most meals, sleeping in a different hotel bed every night, staying active on the road with workout straps and push-ups in the room — it takes discipline and adaptability. It also takes a support system at home that understands the lifestyle. Shane is candid: he hates being away from his girlfriend, and he genuinely dreads the longer trips. But the tradeoffs — flexibility, travel perks, the sheer joy of the job — make it worth it.

The Truth About Maintenance Delays and Turbulence

For nervous flyers, Shane offered some of the most reassuring and practical perspective of the entire episode. When maintenance crews board a plane and passengers start to panic, the reality is almost always far more mundane than it looks. Broken door lock? A light bulb? A trackball on a flight computer console? These are the kinds of things that trigger maintenance calls, not catastrophic failures.

“Most problems they can kick the can down the road, so to speak,” Shane explains. “Every single piece on that airplane has a specified section in the manual that tells us if this piece is broken, it can still fly safely if you do this and this instead.”

If something genuinely serious comes up, the airline swaps out the airplane. Full stop. The goal is always safety — and keeping that machine flying, because airlines only make money when their planes are in the air.

As for turbulence and flying over open water? Shane is equally reassuring. Airlines must be certified specifically to fly over water, and flight plans are required to keep aircraft within a set distance from land at all times — typically an hour to an hour and a half. Every nine months, pilots train in simulators specifically for engine failure scenarios at every phase of flight. It becomes, in Shane’s words, “almost a non-event” because they’ve rehearsed it so many times.

“Airplanes fly just fine on one engine, land just fine, and it doesn’t have to be super scary.”

The Part That Never Gets Old

For all the logistics and challenges of life as a pilot, what Shane keeps coming back to is the wonder of it. The walk-around before every flight, looking up at engines as big as he is and thinking about the physics of what’s about to happen. Watching the GPS scream across a map at 600 miles an hour when you zoom in close enough to see individual towns pass in seconds. Flying into LaGuardia at sunset with all of Manhattan spread out below. Seeing Petra in Jordan, swimming in the Red Sea — countries he never would have thought to visit on his own.

“I wish somebody could just instantly be in my head and see all the places I’ve gone and the views I’ve had from the sky,” he says. “It’s the most rewarding job on the planet.”

And every time a flight ends and a passenger stops to say thank you? That lands too.

Thinking About Becoming a Pilot?

Shane’s advice is simple: start with an intro flight in a small Cessna. See if you love it. From there, the paths are varied — military service, civilian flight schools, university aviation programs. Expect the training to cost between $80,000 and $100,000 going the civilian route, and plan on building hours through flight instruction, banner towing, sightseeing tours, or skydiving charters before the airlines will look at you. It takes time. It takes grit. But for those who feel called to the sky, life as a pilot offers something few careers can match: a front-row seat to the world, literally, every single day.

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Want to hear the full conversation? Listen to this episode of Bon Voyage Besties wherever you get your podcasts, and follow us on social media for more travel stories, tips, and adventures.