The Amazing Race Canada’s Jon Montgomery on the Best Job in the World

To say Jon Montgomery has had a unique career path is an understatement. The 37-year-old has gone from auto auctioneer to Olympic and World Cup skeleton racer to television personality, and also works as a motivational speaker (though, he says it’s up to the people listening to determine whether or not his talks are motivational). We caught up with him before he set off to run around the country—and the world—to film the fifth season of the show.

CAA: What do you love most about your job on The Amazing Race Canada?

JM: Getting to celebrate the greatest part about Canada: its people. The single best thing is to watch people do things that they didn’t think were possible. And watching the look on their faces when they come to the mat, after the most stressful, greatest, most trying thing that they’ve ever done in their lives—I’m the dummy they get to see at the end of that rainbow. 

CAA: In those extreme situations, people’s dynamics are obviously tested. What’s the most important element to great travel partners?  

JM: Communication. It doesn’t matter if it’s on the show or in real life—you need to communicate effectively to be able to travel well with a partner. There was a U.S. version [of The Amazing Race] where they had strangers competing together and they did very well. I think that’s because of the need to communicate: you can’t take it for granted that people automatically know how you’re feeling.

CAA: One of your talks covers how to dream big and go after what you want. Does travel encourage people to that?

JM: Oh, absolutely. If there were something you could do today that made you more adept to deal with challenges and face adversity tomorrow, travelling would do that for you.

And I think it’s really attainable—not necessarily international travel, but even getting in your car and exploring today will allow you to do something bold tomorrow.  

CAA: Is there a destination that you would recommend for that?

JM: It’s definitely a personal choice. Be realistic about where you’re comfortable going. If someplace doesn’t give you peace of mind, don’t go. Go to Saskatchewan, go to Quebec City, go to Newfoundland, go to Fogo Island. The vastness of travel and being able to learn about different cultures—you don’t need to leave Canada to do that.