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Jon Montgomery: Stepping Beyond Your Comfort Zone

Canada’s favourite skeleton racer, Jon Montgomery gained national attention after capturing gold at the 2010 Olympic Winter Games in Vancouver. His hard work on the track, infectious energy and much-loved post-victory celebration all endeared him to people across the country. Since 2013, Montgomery’s stature has continued to grow as the award-winning host of popular reality TV show, The Amazing Race Canada.

We spoke with him for Go Magazine about the importance of stepping beyond your comfort zone, learning from failure and why teamwork is vital to success. Check out the fantastic insights he had to share below.

You’ve got an incredibly impressive resume as an Olympic gold medalist, auctioneer, professional speaker and the host of The Amazing Race Canada. What’s some of the best career advice you’ve ever received?

The best career advice that I’ve ever received was probably when I left home at the age of 18 for Barrie, Ontario to go to the Automotive Business School of Canada at Georgian College. My mom was a realtor and told me, “If you help people get what they need, you’ll in turn get what you want.” That stuck with me and it was all about putting other people’s needs before your wants and desires for a paycheque. I think if you help folks accomplish a goal or a mission, you’ll in turn be rewarded. They’ll respect you, you’ll get repeat business and referrals, and it will snowball and perpetuate what it is you’re trying to do in the world of sales.

I’ve never sold anybody anything, but I did help people solve some transportation problems. I know it sounds cliché to say, but I’m a service-oriented fella and I would never want to sell something that somebody didn’t need to them.

Putting the needs of others first is definitely good advice.

Unless you’re on an airplane and the oxygen mask drops down. Then it’s your responsibility to put it on your face first so you don’t pass out, and then you can help others around you. You’ve definitely got to consider yourself first in that situation, but that’s the only instance!

Season 7 of The Amazing Race Canada is airing now. What excites you about being a part of the show?

The part that excites me the most about each season is getting to reconnect with all the awesome individuals whom I’ve met throughout the years here on the show. From shooters and producers, to sound and tech people, to everybody that makes this amazing program a reality. I love having the opportunity to be a part of something bigger than myself and working collectively with others towards a common goal. It’s a source of pride for me to be associated in any way, shape or form with such a cool group of cats.

Contestants on the show are regularly pushed outside of their comfort zone. Why do you think it’s important for all people to regularly challenge themselves – whether it’s for a race, in their career or in their personal lives – and take new risks?

You can’t grow and develop when you consistently and religiously stick within this little tiny sphere of comfort. Where you’re comfortable is not where life begins. Instead it’s at that threshold of your comfort zone – and when you go beyond it – where you find out both what is worth living in life, and what makes it rich and invigorating. That comes from challenging yourself. That comes from finding new opportunities to fail, to get better and then be victorious in overcoming some of the challenges that you present for yourself.

I honestly believe that when people undertake the challenge of being on The Amazing Race Canada, they are in a position to have a major metamorphosis. We’ve seen it season over season with people who didn’t win leaving the show with an incredible sense of pride in their accomplishments and the realization of what they can achieve in life. And that starts with living right at that threshold of where you’re comfortable. Beginning to step beyond those boundaries is when you will grow and develop.

When beginning to push past their boundaries, most people are going to have mishaps and setbacks. From your own experiences, how have you learned to not let these things deter you from going forward?

You’re never a loser if you take a lesson away from a failed attempt. The only thing that makes you a loser is when you quit and when you give up on yourself or somebody else. The notion of quitting and giving up doesn’t sit well with me. People trying and failing makes me so proud. Trying, failing and quitting? That doesn’t make me proud. Taking what you learned in that attempt allows you to have a better chance for success next time. To apply it to a different situation to ultimately be victorious, to grow and to develop. And that doesn’t happen without failure. People talk about failing faster to get to where you want to be because failure is where the growth happens.

From what you’ve witnessed on The Amazing Race Canada and even from your own experience with the crew behind the scenes – why do you think teamwork is so vital to success?

We’ve all got our individual areas of expertise. But alone we’re fairly siloed. You can’t build a complete picture as individual experts. You need to work together with people who are equally gifted at areas that you have no clue about. This show brings together an amazingly talented group of individuals who are all willing to collaborate, who are all willing to give everything of themselves in their area of expertise to contribute to something that is bigger than that one item that they’ve lent their skill set to. At the end of the day, when you have all these collaborators working diligently towards this common goal and putting this show first above everything, from their personal safety in some instances, to definitely their personal comfort, it’s rewarding.

Based on what you’ve experienced in your personal life or from your work as an athlete or with The Amazing Race Canada, is there anything you’d like to see changed about the world of insurance? 

I think that people particularly in the province of British Columbia should pay insurance on the price of their car. I don’t think that dudes driving supercars worth $250,000 should be in the same category as myself, based on insurance replacement costs and the cost to fix these cars. If you can afford a $250,000 car, you should be able to afford the repairs if you’re driving irresponsibly. I shouldn’t have to, and nor should my peers have to, foot the bill for something that’s not even within our realm of possibility for approaching in terms of a consumer product, and I don’t think that we should be grouped together in that same category.

You can learn more about Jon Montgomery on his website here. The Amazing Race Canada airs on CTV. Learn more about it here.

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