Retirement: The Beginning of Something Bigger?

Estimated read time: 4 minutes

Welcome to My Musings – a space where I unpack myths, share personal reflections, and offer pragmatic strategies for navigating life and work's twists and turns.

Today’s Musing: Why is retirement seen as an end? Really, it’s a beginning - a chance for reinvention, growth, and purpose.

Retirement: The Beginning of Something Bigger?

Last week, I sat on a panel discussing retirement put on by the good folks at Rosie’s Roadshow. The audience? Folks either stepping into retirement or already navigating its waters.

Retirement is a topic I find fascinating, particularly:

  • What happens when people retire.

  • What fears surface at this stage of life.

  • What opportunities retirement might bring.

What struck me during the panel was the overwhelmingly negative focus from my co-panelists. To be fair, that wasn’t their intention, but the future they described felt bleak:

  • “You’ll get sick.”

  • “You’ll need to plan for your funeral.”

  • “You’ll never have enough money for what’s coming.”

  • “Your kids will fight over your estate—maybe even before you’re gone.”

I’ll admit, I might be a tad naive. I’m a middle-aged guy in decent health who isn’t exactly losing sleep over stairlifts or step-in baths (though, let’s be honest, those do look amazing).

But what puzzled me was the automatic leap from "retirement" to "death." The discussion wasn’t about life after work—it was about illness, decline, and estate planning. It seemed to leave out life entirely.

Why does retirement so often come bundled with doom and gloom? Is it because we see it as the last act, the “final chapter”? Does “retirement” have to mean fading away?

Reframing Retirement: A New Lens

Retirement isn’t the end of the story—it’s a transition. According to Herminia Ibarra in the HBR Guide to Designing Your Retirement, retirement is not an objective change of role but a process of moving from a known working life to an unknown future. This can feel unsettling because work often shapes our identity. Ibarra notes that many struggle in this transition, especially with the “messy middle”—a phase where conflicting desires and uncertainty dominate.

However, I see retirement as an opportunity. Derek Milne, in The Psychology of Retirement, captures it beautifully:

“Retirement: is this our final act, the dimming of the light, the inescapable descent into hopeless senility? The traditional answer is an emphatic ‘yes’...But recent decades have seen a transformation in the possibilities that are ushered in by retirement.”

This was the message I tried to convey on the panel. While others focused on powers of attorney and knee replacements, I saw something different: a chance for reinvention.

Retirement or Transition?

Ibarra also emphasizes the importance of experimenting and learning as part of navigating retirement. Instead of jumping into the void, she suggests trying out new roles, projects, or activities to reshape one’s identity and life structure gradually. This experimental approach is key to finding what works​.

Retirement isn’t so different from other life transitions—like leaving a job or switching careers. Both can feel final, like closing a chapter forever. And that sense of finality can be overwhelming.

So, how do we navigate this? How do we turn retirement into something hopeful?

Two Paths Forward

Stephen Levine’s A Year to Live

Imagine you have one year left—just 12 months to finish your unfinished business. Levine’s approach encourages us to take the possibility of death seriously—and do something about it.

What would you prioritize? Reconnecting with old friends? Pursuing a long-lost dream? Having tough conversations you’ve been avoiding?

While this exercise might sound morbid, it doesn’t have to be. It’s a powerful reminder to live intentionally. And here’s the best part: You don’t need to be dying or retiring to try it.

Herminia Ibarra’s "Messy Middle" Approach

Ibarra’s concept of experimenting in the “messy middle” can guide those feeling unmoored by retirement. This involves:

  • Experimenting: Try new hobbies, roles, or side projects to discover what excites you.

  • Reframing: Shift your perspective on what this phase of life could mean.

  • Building new networks: Connect with communities or mentors to explore opportunities​.

By seeing retirement as a time to experiment, you transform it from a period of decline into a phase of growth.

Derek Milne’s RECIPE Framework

For a more structured approach, Milne offers the RECIPE for a fulfilling retirement:

  • Resources: Financial stability.

  • Exercise: Physical health and activity.

  • Coping Strategies: Emotional resilience.

  • Intellectual Activity: Lifelong learning.

  • Purpose: Meaningful goals.

  • Engagement: Social connections.

Thriving in Retirement

Retirement doesn’t have to be the end of the story. It can be a vibrant new phase—a chance to grow, adapt, and thrive. By embracing intentionality, leaning into frameworks like RECIPE, and experimenting as Ibarra suggests, we can rewrite the narrative around retirement.

So, here’s the question: How do you want to define your next chapter? Will you let it be written for you, or will you take the pen and write it yourself?

Want to Get on the Path?

Curiosity is the spark that ignites change. If you're ready to explore what’s next in your career or life, let’s start a conversation and see where curiosity takes us.

Let’s talk.

I hope this week’s musings offered a new perspective. See you next week.

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