He knew everything about retirement, except how to live it

After 36 years in banking, Mike Drak thought he was ready for retirement. He had a solid pension, a strong investment portfolio and decades of experience helping others plan for their financial future.

He had everything — except a plan for what came next.

“I thought retirement would be easy,” Drak told me. “But it wasn’t. I was in a dark place. I lost my identity. I had the money, but I didn’t have a plan for life after the office.”

This isn’t a story about poor planning. It’s about how you can do everything right financially, and still not be ready for retirement.

The victory lap

I first discovered Mike’s work in 2016 when I picked up a copy of his book, Victory Lap Retirement: Work While You Play, Play While You Work. I was wrestling with my own questions about what would come next after a high-pace career. Drak’s book challenged the idea that retirement was the end goal and introduced the concept of the victory lap: a phase of life in which you mix purpose, play and work on your own terms.

I reached out, and in the years since we’ve become good friends. We’ve shared ideas, supported each other’s work and even done a little fishing together.

Drak and I chatted earlier this month about his victory lap, and the importance of a holistic retirement plan.

“The system taught me how to save,” he told me. “But no one taught me how to live after work.”

Despite decades working in financial services, Drak was unprepared for the emotional reality of retirement. He went through what he calls “retirement hell,” a painful period of identity loss, disconnection and uncertainty. He realized that while the industry focuses heavily on building wealth, it leaves clients unprepared for what happens once the paycheques stop.

“I had enough money,” he said. “But I didn’t have a life plan. That part I had to figure out myself.”

Drak didn’t stay in the dark for long. In addition to Victory Lap Retirement, he published Retirement Heaven or Hell: Which Will You Choose? and Longevity Lifestyle by Design: Redefining What Retirement Can Be. Both are available for free at Booming Encore.

He began mentoring others, leading workshops and helping retirees build what he calls a “second life,” defined by purpose and possibility.

Advice for advisors

“Clients need more than a drawdown strategy,” Drak told me. “They need a blueprint for meaning.” He offered three recommendations for financial advisors:

1. Talk about life, not just money. Clients are rarely asked what they want life to feel like after work ends. Don’t stop at the retirement date or savings goal. Ask clients what their Tuesdays will look like. What makes them feel alive? How do they want to stay connected, creative and useful?
2. Prepare clients for the emotional shift. The first six to 12 months after leaving work can be disorienting and even depressing. Structure disappears. Social circles shrink. Identity fades. Clients may feel guilty bringing it up or have difficulty articulating their worries — especially if they’re on solid ground financially. Initiate the conversation. Tell them that the transition is difficult for a lot of people, and that retirement planning includes both a financial and emotional dimension.
3. Build your network of non-financial experts. You don’t have to do it all. Connect clients with retirement coaches, psychologists, health professionals and others who help people figure out what a victory lap looks like for them.

It’s not enough to prepare people financially, Drak told me. We must help them build a plan that includes identity, community, contribution and health. Advisors have a choice — keep selling plans for a retirement that no longer exists or help design second chapters that clients are excited about.

Drak is 70 now, focused on training for an oversized victory lap in the form of the Ironman triathlon in Ottawa this summer. In the decade since we met, he’s grown increasingly inspirational to me.

He doesn’t want to be seen as exceptional though. Drak’s retirement, in both its ups and downs, is a signal all of us should pay attention to. Retirement cannot be prepared for with products alone. Let’s ensure clients have the tools, advice and support necessary to thrive in a retirement that can last decades.