Rethinking the Role of Work in Retirement

I’m currently reading Killing Sacred Cows, a book that explores several financial myths we’ve come to accept as truth. Over the next few months, I’ll be sharing a few of these insights with you. Today, I want to focus on the evolving concept of retirement—specifically, the myths around work and what it really means to retire.

Not long ago, we discussed helping clients rethink retirement, including the idea that many people continue to work even after they “retire.” This month, we’re diving deeper into the true role work plays in our lives—emotionally, mentally, and socially.

The Evolution of Work: From Vocation to Identity

A century ago, work was often seen as a calling—think of the butcher, the baker, the candlestick maker. People took pride in their trades, often passing them down through generations. That changed during the Industrial Revolution, when work became more about efficiency and less about purpose. Unfortunately, that shift also distanced many people from finding meaning in what they do.

Still, work remains a major part of who we are. It defines our social circles, shapes our worldviews, and gives us opportunities to explore our strengths and weaknesses. Work helps us feel productive and needed—two feelings that don’t simply disappear after age 65. In fact, many retirees find themselves bored or unfulfilled when they stop working entirely. Total leisure sounds great on paper, but for many, it’s a one-way ticket to discontent.

Today, we define work more broadly:
“An engagement that brings value to others and meaning to me.”
By this definition, work includes both paid jobs and volunteer efforts, making it a more inclusive part of one’s life journey—not something you walk away from at a set age.

Retirement Realities: It’s Not All Hammocks and Tee Times

At Gainplan, we work closely with clients transitioning into retirement—and what we’re seeing is a clear trend: people don’t want to stop working, they just want to work differently. Whether for economic reasons or the need for purpose, more individuals are seeking a balance between leisure and contribution.

The 15th Annual Transamerica Retirement Survey said it best:

“Baby Boomers are revolutionizing retirement by overturning long-standing assumptions… and proving that retirement and working are not mutually exclusive.”
In fact, only 21% of respondents said they would stop working entirely.

The problem? Most workplaces aren’t ready for this shift—only 48% of employers say they can accommodate older workers who want to stay engaged. That’s where thoughtful planning comes in. It’s not just about financial readiness—it’s about building a future that includes purpose, structure, and identity.

The Unspoken Challenges of Retirement

Beyond finances, retirement brings a wave of non-monetary challenges. Many people struggle with:

• Loss of identity – Who are you if you’re no longer “Dr. Jones” or the go-to expert in your field?

• Social shifts – You may genuinely miss your coworkers or clients.

• Reduced mental stimulation – Can a crossword or daily walk truly replace decades of strategic thinking?

• The paycheck psychology – Even with enough money, some struggle to justify everyday spending.

• Too much free time – Are you fixing things that don’t need fixing just to stay busy?

These risks are real—and we see them firsthand in the stories our clients share. A 2020 study from Oregon State University even found that those who work longer tend to live longer. That’s not a coincidence. Staying active, challenged, and connected is crucial to maintaining a high quality of life.

Final Thoughts

Our clients are unique, and so is their retirement vision. Cookie-cutter advice doesn’t cut it anymore. They rely on us not just to manage their money, but to help them design a life with meaning. Yes, financial security matters—but so does the emotional, social, and intellectual fulfillment that work can provide. Helping clients navigate both is where true planning happens.

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