Over the next 20 years, millions of Canadians will step into retirement. That includes the youngest baby boomers, who will hit 65 by 2030, all of Generation X and even the oldest millennials, now turning 45.

Unfortunately, retirement can easily bring a loss of purpose and identity, especially if work previously provided that. One survey finds that three in 10 retirees report emotional challenges in making the transition. Another study finds higher satisfaction among those who view retirement as a “new start” and greater dissatisfaction among those who see it as an  “imposed disruption.”

No matter how close they are to leaving work, many people wonder what life after their careers will look like. Most begin with logistical questions: When should I retire? Will my savings last? Where should I live? Some will also picture how they’ll fill their days: Travel? Volunteering? Hobbies? Pickleball, anyone?

But Maja Djikic, associate professor and executive director of the Self-Development Laboratory at the Rotman School of Management, says that kind of planning overlooks something essential.

Retirement isn’t just the end of work. It’s a major life transformation that can open exciting possibilities.

“There’s this belief that your value comes only from the working world,” she says. “And when you stop working, you become valueless. You may as well just amuse yourself, which is where the idea of picking up a hobby comes from.”

A fulfilling retirement, she says, is more meaningful. It’s about looking inward, continuing to grow and discovering parts of yourself you didn’t have time — or permission — to explore while building a career.

So what holds people back? Several things:

The first is letting go of old ideas about what retirement is “supposed” to be and becoming curious about who we can still become. The second is rediscovering underdeveloped parts of ourselves. Djikic calls them “the parts we left behind.”

These left-behind parts may be creative, social or intellectual. Often, they’re early interests pushed aside because parents or teachers discouraged them, or they didn’t fit a chosen career path. In retirement, reconnecting with these forgotten sides can make life richer.

And that’s where people get stuck. After a 40-plus-year career, we tend to stick to the familiar. As we search for meaning in retirement, we revert to what worked in the past.  “People identify with their successes. And for many, work is tied to success,” Djikic says.

Take someone who grew up shy and analytical, became a financial analyst and built a solid career, though preferred working alone. Even with decades of experience, they might feel uneasy in new social situations. So in retirement, they stick to solitary walks and volunteer their financial skills at a non-profit from their basement. That’s fine, but their undeveloped social side may quietly limit their ability to grow.

Conventional advice for the retired analyst might say: join a club, talk to strangers, get out of your comfort zone. But Djikic says that approach rarely works because it tries to change only one part of a complex system.

The human self, she says, has five interconnected parts: motivation, behaviour, emotion, mind and body. The “just push yourself” method targets only one part: behaviour. “It’s like trying to push one spoke of a spinning wheel one way when the rest of the wheel is spinning the other way.”

Real transformation happens only when all five parts move together. That requires an integrated plan that makes new directions in retirement feel natural, not forced, says Djikic, whose book The Possible Self: A Leader’s Guide to Personal Development explores these ideas.

So where to begin? She suggests two shifts that can open new ways of thinking about retirement.

Move from “I was” to “I am becoming.” People often anchor identity in their past: “I was a doctor.” “I was a business leader.” But clinging too tightly to who we were limits who we might become.

Shifting to “I am becoming” gives the mind space to imagine our next possibilities, Djikic says. A retired doctor may begin writing a novel; a former executive might find purpose in civic engagement or running for local office. “So we start to think of and communicate about ourselves differently,” she says.

Shift from strengths to vulnerabilities. As retirement nears, people tend to look backward at the strengths that built their careers as wayfinders. That’s natural, but it can trap us. Our strengths aren’t our full selves. Vulnerabilities often point to the underdeveloped parts we abandoned long ago.

Consider that shy analyst from earlier. Their discomfort with social situations may stem from old hurts: childhood bullying, embarrassing situations. And so their underdeveloped social side may limit what they feel able to do in retirement. “When we work directly on healing some of these old wounds, we discover a capacity we didn’t know we had,” Djikic says. “The social world suddenly seems attractive and full of energizing opportunity.”

When should people begin this work? Right now, she says. Whether retirement is two years away or 20, “if you work on your human self, retirement won’t feel like retirement. It becomes a constant state of becoming.”

And that ongoing growth, she says, is what truly makes life after a successful career fulfilling.

For leaders looking to plan their legacy, learn more about Rotman's Distinguished Leadership Initiative.