Norton Secured powered by digicert Colin Maitland and his wife pose for a photo in front of a plane he flies frequently.

Employee & Agent Stories

Dreams of Flight Reinvigorated and Shared

Colin Maitland has always dreamed of flying. Growing up in Canada, he aspired to be a fighter pilot in the Royal Canadian Air Force. But a lack of 20/20 vision effectively halted that dream.

“There was some obvious disappointment there,” he says. “There are certain things you can’t control. That just happened to be one thing I wasn’t able to do.”

That didn’t stop Colin’s love of planes, though. As a teenager, he continued to build model aircraft and later joined the Royal Canadian Air Cadets. He didn’t get as much exposure to actual flight training as he had hoped, and after three years, he moved on.

“I got out and sort of parked the dream on a shelf thinking that maybe one day I’d get back to it,” Colin says.

Colin moved into a computer science career. Time passed, and Colin’s dream of flying stayed dormant. Then came a Fathers’ Day gift in 1998— a gift that Colin’s wife, Cindy, has called “the best and worst gift” she’s ever given him.

It was a gift certificate for a flight demo, a one-hour introductory flying lesson. “I said, ‘Oh, this is kind of cool,’ and put the certificate in the junk drawer,” Colin says. “So every time I opened the junk drawer, I’d say ‘Oh, I’ve got to remember to do that.’”

Nearly a year passed before Colin opened the drawer and noticed the certificate’s expiration date was near, finally pushing him to schedule the lesson. It didn’t take much for him to regain the passion he found in his youth.

“As soon as those wheels left the ground, I knew that the total freedom and adventure I was going to get was something I wanted to grab on to as much as I could.”

With more time on his hands, a little more financial wiggle room and his children at ages where they didn’t require non-stop attention, Colin dove back in headfirst.

Five months after that demo, Colin had completed his training and earned his pilot’s license. And 19 years later, he’s still flying regularly and loving the time he spends in the air.

Colin estimates that he flies once or twice a month, using a plane owned by the Capitol City Flyers, a local Madison flying club of which he’s a member.

And on most of those flights, he and his wife are simply heading out to grab breakfast or lunch.

Their favorite spot is the Piccadilly Lilly Airport Diner at the Tri-County Regional Airport near Lone Rock, Wis. A quick, low-altitude flight from the Dane County Regional Airport takes Colin and Cindy along the meandering Wisconsin River and over picturesque bluffs en route to a delicious breakfast.

“It’s a pretty flight, it’s relatively short and there’s a purpose involved in that you’re going to get fed,” Colin says. “It makes for a nice relaxing and enjoyable day.”

Colin Maitland and his wife pose in front of a plane he often flies.
Colin Maitland and his wife pose in front of a plane he often flies.
An aerial photo of the American Family campus.
Colin and a passenger enjoying a flight.
A plane often flown by Colin sits in the snow.

When Colin takes along a first-time flier, the Lone Rock route is his go-to. By his count, he’s shared his passion with over 100 passengers, and they almost always love it.

“I know of three that I’ve taken, though, that have had to take advantage of the ‘sick bag,’” he adds in between laughs. “The first time that happened, I was not prepared. I learned my lesson from there on to have a bag ready in the plane.”

Those three trips aside, Colin says, his introductory flights have inspired a new passion in many of his friends. “I have one friend that’s always available at a moment’s notice. I can send him a text, and he’ll be (at the airport) half an hour later,” Colin says.

Colin continues to share his enthusiasm with flight fanatics on the second Monday of each month at The Jet Room in Madison, Wis., a restaurant inside the Wisconsin Aviation Building with full-window views of the airport runways.

The group is a mix of pilots, soon-to-be pilots and flight enthusiasts — and most of them happen to be American Family Insurance employees. Colin, now a technology solution delivery manager at American Family Insurance, organizes the get-together and welcomes anyone curious about flying.

Within the first five minutes of sitting down, the conversations quickly turn from work-related small talk to discussions of flight hours, recent trips and who’s next to earn their pilot’s license. Even as burgers and sandwiches are placed in front of them, the discussion ensures they’ll be eaten at a slower-than-average pace.

“It’s sort of like people that are really into sports cars. You get a group of them together, and they start talking about RPMs, horsepower, fuel-injected stuff,” Colin says. “You have to do work to make it happen. People just don’t magically meet. But once you get them you can’t get them to stop talking, that I know.”

To an outsider, the concept of learning to fly a plane might be overwhelming — but Colin insists that any fear a non-pilot has about learning to fly quickly evaporates during training.

“If I can do it, anyone can do it. I can see where it’d be fearful from the outside looking in, seeing all of the buttons and gauges, but it’s not overly complex,” Colin says. “It’s a different type of adventure than you would normally have with driving a car to work every day. You just have to prepare yourself and learn what’s necessary in order to operate that vehicle safely.”

Colin is quick to credit his wife for pushing him back into his hobby and dealing with his obsession with planes. “I love flying a lot more than she loves flying,” he says. “I’ve been very, very fortunate that one of my dreams has come true.”

And while he continues to live his dream gliding along Wisconsin’s skies a handful of times a month, it still doesn’t come close to being the best thing in his life. “Flying is nice, it’s a recreation, but nothing is more important than the family I have. Great wife, great kids, and that wonderful little girl.”

That wonderful little girl is Colin’s one-year-old granddaughter, Saoirse. “Maybe we’ll get her involved in flying,” he says.

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