Since retiring at age 58, Tim Cowley has been able to focus on travel, fitness and coaching pickleball.Getty Images
In this new series, Sliding Doors, we explore real-life crossroads that shape personal ambition: Take the leap or play it safe? Move forward or pivot? We talk to people who faced real-life decisions and speak to experts about the consideration and intuition behind these choices.
As a trained pickleball coach, Tim Cowley can help you improve your game, but you may learn even more from what he has to say about improving your life.
“I took early retirement two years ago at age 58 and I’ve never looked back. I had a great career, but then a couple of friends passed away and I started to wonder whether I was still enjoying work. I realized that I didn’t want to do what I was doing any more,” says the Vancouver-area resident, who worked in sales throughout his career.
“Now, I coach pickleball, my wife and I travel, and our schedule belongs to us,” he says.
Making a big, life-changing move is often known as a “sliding door moment.” The name comes from the 1998 movie Sliding Doors starring Gwyneth Paltrow, whose character tries to catch a subway train after getting fired. In one storyline, the train doors slide open, she gets on and stays with her boyfriend; in an alternative storyline, the doors slide shut and she leaves him and falls in love with someone else.
Mr. Cowley’s alternatives were perhaps not as movie-plot dramatic as this, but he does believe that going through the right sliding door may not just change your life. It may save it.
Stepping though and doing something different has helped him and his wife build an optimistic future, he says. Since retiring, he has been diagnosed with diabetes and arthritis and his wife, a yoga instructor, has been treated for heart problems.
“We focus on fitness goals, but we have a new normal. We have to slow down and take breaks,” he says.
Financial and emotional changes
Deciding when to retire is much more than a financial move, says Mr. Cowley. He explains that his major financial decision was to entrust professional advisers with managing the details, allowing him and his wife to focus on living off their retirement funds and a modest income from his coaching side business, Elevate Pickleball, which he co-founded with a younger partner.
“The company brings in a bit of money, but I’m in it for the coaching,” he says. He expects that he and his wife can travel, enjoy fitness and the outdoors and manage on their funds for 30 years. “Really, how much money do you need?”
While it may sound delightful to walk away from full-time work forever, it’s not necessarily easy on the emotional side, Mr. Cowley says.
“It took me about six months. It’s hard when you work your entire life and that’s what you know. It’s your identity. I loved going to work but then it got to where I just didn’t love it any more. It doesn’t happen all at once, but it gets to the point where your enthusiasm ebbs and flows,” he says.
Take time to decide
“Deciding when and how to retire is rarely the result of one thing,” says Mary Morency, a Montreal-based retirement coach. Over nine years, she has advised more than 450 people on going through the sliding door of retirement, and together with her coaching partner Jeannette Lalonde wrote a book in 2021 called Rethinking Retirement – a Guide for Making Choices.
It’s wise to take time to make the decision, as Mr. Cowley did, she says.
“To thrive in retirement, it is best to spend some time thinking about the lifestyle you want and then start putting some plans in place. It takes work to avoid the sensation of stepping off a cliff once you decide to retire,” Ms. Morency says.
“Obviously being financially prepared is critical, but knowing when to retire and how to thrive goes beyond the financials.”
Early retirement enabled Tim Cowley, left, to play more pickleball too. Here, he celebrates a tournament silver with doubles partner Rommel Ramirez, in Whistler, B.C., in September, 2023.Supplied
Consider your purpose
Ms. Morency and Ms. Lalonde suggest that people who are considering retirement put their decision into a framework that has four key components.
The first is to ask yourself what kind of contribution to the world you want to make after you leave full-time work.
“Consider what you want to retire to rather than from before you retire,” she says. “You’re letting go of your professional identity, and you’ll feel more comfortable with your decision once you figure out how you’ll replace the things that are important in work – structure, usefulness, people and status.”
The next thing to consider is your post-retirement purpose, Ms. Morency says.
“Think about what you are passionate about. It often involves reviving a passion put aside years ago; identify your true character strengths, what makes you shine,” she says. In Mr. Cowley’s case, he had long experience coaching basketball and tennis, so pickleball was an easy step.
Ms. Morency’s third consideration is connection.
“Many people fear feeling invisible after a long career. Some people need to relearn how to make friends, and doing this before they retire strengthens their level of comfort with the decision to retire. Couples, especially, benefit from reflecting and planning together,” she says.
Finally, consider your overall well-being, she says. “People weigh the pros and cons of juggling their careers and health issues and decide that the latter is more important.”
That’s a choice that Coach Crowley agrees with heartily.
“You have to get out there and live the life you deserve, before it’s too late,” he says.
