Jon Montgomery Shares Lessons from Skeleton Racing and Life

By Quinn Martindale ’26

In December, Canadian Olympic gold medallist and host of The Amazing Race Canada, Jon Montgomery, visited Ridley. As the second MGI Gordon speaker, Montgomery spoke about his experience at the 2010 Vancouver Olympics, how he discovered skeleton racing and why he believes in giving 110 per cent in everything he does.

Jon said his path to skeleton was a process of elimination.

“Skeleton is about as niche as it gets,” he said. “After university, I moved to Calgary and wanted to engage in a sport that could be a vehicle on my journey to represent Canada. That was the ultimate goal: wearing the Maple Leaf on an international stage.”

He tried speed skating first, then saw a skeleton race for the first time.

“I didn’t even know what I was witnessing at first. I thought it was an accident,” he said. “But a week later, I took my first run and I knew this was it. It was going to be hard, full of trials and tribulations, but I loved it enough to embrace the work ahead.”

Representing Canada was always the dream, he said, whether at the World Cup, Europa Cup or the Olympics.

“The Olympics were the big dream, but even reaching a smaller stage would have been fulfilling,” he said.

Jon said the journey to that level was unpredictable.

“You never know where any road will lead. Life plans change constantly. The key is doing things that scare you and stretching yourself beyond your comfort zone. Every hard thing you do teaches a lesson, even if you fail.”

He applied lessons from hockey, baseball and golf to skeleton, observing others and identifying weaknesses.

“I asked myself, ‘Why not me?’ If a friend of mine could win Olympic gold, why couldn’t I?” he said. “That mindset rooted my goals in reality.”

He shared that comparison can be harmful if it comes from entitlement, but it can also be motivating.

“If you see comparison as proof of what’s possible, it can be motivating,” he said. “Ask, ‘Why not me also?’ If they can do it, it’s achievable. Give everything you have and if you fall short, you’ll know you tried.”

Competing at the 2010 Winter Olympics in Canada brought added pressure, but Jon said he viewed it as support rather than expectation.

“I was intent on being present and savoring every moment, knowing I’d never get another chance to compete at a home Olympics,” he said. “I didn’t internalize Canadian interest as pressure. I saw it as energy.”

He brings that same energy as the host of The Amazing Race Canada. Montgomery said his role as host of is about connecting with racers during intense moments.

“Sometimes I coach them, especially when they think they’re eliminated but aren’t,” he said. “I want them to dig deep and show Canadians what they’re made of. Curiosity is my greatest asset. I love asking questions and learning about people.”

His personal motto is simple: “Get ’er done. Believe it’s possible.”

“Confidence isn’t something you hope for; you build it,” he said. “Believe, then act.”