Chris Rudge, seen here in Toronto, reflects on the first 13 years of his ‘retirement.’ (Jennifer Roberts/The Globe and Mail)

Chris Rudge, who has retired by his estimation three times, is becoming something of a dab hand at the whole retirement game.

Not that he’s choosing to put his feet up at 71 and take it easy, however.

After working the bulk of his career as a printing executive, Mr. Rudge left Quebecor at 56 and seized several opportunities that allowed him to use his expertise in a beneficial way.

That has ranged from guiding the Canadian Olympic Committee to new heights at the 2010 Vancouver Olympics to organizing the 100th Grey Cup in 2012. In addition, he has helped to bring in the Own The Podium program in the runup to the Vancouver Games, which has since helped numerous Canadian athletes to realize their Olympic and Paralympic ambitions.

If he’s learned anything from a hat trick of retirement attempts, it’s that he needed to retire to something, not from something.

When he first ‘retired’ in 2001 at age 56, it didn’t take Mr. Rudge long to discover that it was someone else’s retirement dream, not his. Now 71, he’s still working, albeit at a somewhat slower pace. (Jennifer Roberts/The Globe and Mail

“What I discovered early in life is that my level of comfort is essentially discomfort, and by that I mean that I always need challenge,” he says from poolside in Costa Rica, where he estimates he spends 30 per cent of his time now.

However, that’s not to say he knew exactly what he was getting himself into in 2002 when he retired the first time. After a fulfilling career, during which he juggled teaching duties at Western Tech in Toronto with the demands of being a professional lacrosse player, to working his way up to the executive level at Quebecor World Inc., a printing subsidiary of Quebecor Inc., Mr. Rudge found himself considering his options.

He took a year off, worked out heavily at the gym and played golf three to four times a week. But it didn’t take him long to discover that this was someone else’s retirement dream, not his.

“I need the intellectual stimulation of work, the social stimulation of work and being around other people and sharing thoughts and ideas and having things to accomplish,” he says.

So he looked for a way to merge his two passions of sports and business.

Around the same time, the Canadian Olympic Committee was looking for a new chief executive officer, and after an exploratory interview he was offered the position in early 2003. Not long after, Vancouver won the rights to host the 2010 Winter Olympics, where Canada ultimately won a record 14 gold medals.

Every time I did retire I knew that I wasn’t going to find a chair, read and play some golf. There had to be intellectual stimulation, there had to be social engagement. Chris Rudge

“That was a tremendous run and it really combined my passion for sport and the experience that I had in business,” he says. “So that finished, my contract was up after the Vancouver Games. I had no interest in staying there; it was pretty hard to top what we did there.”

Retired once more, Mr. Rudge wasn’t left sitting on his hands for long. David Braley, a former Canadian senator and owner of the CFL’s B.C. Lions, had just bought the Argonauts in early 2010. With the 100th Grey Cup looming just two years later, he wanted Mr. Rudge to run the team and the festival that would surround the landmark occasion.

Intrigued by the proposition, Mr. Rudge helped to ensure a memorable Grey Cup festival for Toronto, highlighted by the Argonauts hoisting the cup for an unprecedented 16th time. He then stayed on to help attract the attention of Bell Canada Enterprises Inc. and Toronto businessman Larry Tanenbaum, who bought the franchise in late 2015.

His work with the Argos done, that transaction also heralded a third retirement for Mr. Rudge, who, on reflection, was more than happy with the way he had spent the first 13 years of his “retirement.”

“Every time I did retire I knew that I wasn’t going to find a chair, read and play some golf,” he says. “There had to be intellectual stimulation, there had to be social engagement. There had to be a creative challenge that would stretch me in areas that I hadn’t explored in life.”

While he says both the COC and Argos positions required almost as many hours as he was putting in with Quebecor, the British-born Torontonian was now looking to dial down the intensity a bit. He is currently chairman of the board for Niko Resources Ltd., a Calgary-based oil and gas company that is undergoing financial restructuring as it looks to sell the balance of its assets and leases. Mr. Rudge estimates the position demands 10 to 20 per cent of his time.

After a career as a printing executive, Mr. Rudge came out of retirement to take top jobs at the Canadian Olympic Committee and then the Toronto Argonauts. (Jennifer Roberts/The Globe and Mail)

“There are new things coming up all the time, and you’ve got to make sure you’re on top of good governance because you’re helping management with guidance and good questions and how to make good decisions … not unlike teaching,” he says.

But though he may have dialed back his work commitments, he doesn’t plan on stopping the search for other avenues that might pique his interests.

“I will continue to look for other things that might be different, that will gain and stretch me,” he says. “I don’t see this coming to an end, I think at some point I will fall out of a chair and into a coffin and that will suit me just fine.”

In addition to his work with Niko, Mr. Rudge serves on other boards, such as those of the Canadian Sports Institute and the Toronto Pan Am Centre Advisory Council. He also sits as executive-in-residence at the Rotman School of Management Director Education and Certification program at the University of Toronto, where he also lectures as part of the continuing education program.

His role as a guest lecturer provides him with some of his most rewarding work in retirement. Given that the continuing education program attracts older, accomplished people as a rule, many who are also in retirement, Mr. Rudge says that they are naturally curious and not afraid to ask good questions, providing the opportunity for a really informed debate on a number of topics.

“If they get half as much out of it as I do, then everybody’s happy,” he says. “I love it.”

One of the challenges that Mr. Rudge has encountered in retirement is managing his money, partly because as he dials down his work commitments, the income streams aren’t the same.

“You have to be careful in how you manage your money, what you do,” he says.

As a way of modestly adding to his income streams and mostly as a creative outlet, Mr. Rudge has taken up woodworking when he is in Costa Rica, crafting unique charcuterie boards that he sands and waxes on the beach while drinking a margarita.

When he’s not enjoying Costa Rican life, Mr. Rudge travels, although he still finds time to get to the gym on a daily basis. But whatever he does, he ensures that it is something he is passionate about, a philosophy he encourages anyone who has recently retired to employ for themselves.

“Don’t stop moving … and find a series of challenges that will excite you and stimulate you and make you want to get up every day,” he says. “That could include work, that could include philanthropic activities, however you decide to do it, things that you get up and say ‘I can’t wait to get up because I’ve got this [to do].’”