Summary

Retirement is often framed as a personal milestone—a moment when we step away from work and into freedom. But what if retirement isn't just about leaving a job? What if it's about navigating the deep relationships, identity shifts, and responsibilities we carry with us into what comes next?

In this episode of On the Brink with Andi Simon, Andi speaks with Katherine Crewe, a Tech/Vistage chair in Canada, whose thoughtful approach to retirement reveals a powerful truth: transitions are not events—they are processes.

The Myth of the Clean Exit: Leaving Work Isn't Leaving Relationships

Katherine's story challenges the idea that retirement is a simple, clean break. After decades in biomedical engineering and leadership, she moved into a role guiding CEOs and executives. Now, in her late sixties, she is not "done"—she is reflecting, recalibrating, and carefully designing her transition.

What makes her journey so compelling is this: she is not just leaving a role—she is stepping away from a community.

As a chair, Katherine has built deep, trusted relationships with the leaders she supports. When she began discussing retirement with them, the reactions were emotional and varied. Some encouraged her to stay. Others supported her decision. Many wanted one thing above all—a thoughtful, gradual transition.

This wasn't about replacing a position. It was about preserving relationships, continuity, and trust.

Retirement Is a Social Transition, Not Just a Personal One

One of the most important insights from this conversation is that retirement impacts more than the individual.

Katherine realized that stepping away from her role felt less like leaving a job—and more like leaving a network of meaningful human connections. The responsibility she feels is not just to herself, but to those who depend on her leadership.

This is a critical lesson for organizations as well.

As Andi notes, companies are facing a "senior tsunami"—a wave of experienced employees approaching retirement. Yet many organizations still treat retirement as an administrative process rather than a cultural transition.

What Katherine is modeling is something different:

• Thoughtful succession planning
• Gradual transitions
• Honoring relationships and institutional knowledge

This is where anthropology becomes powerful. It helps us see what is really happening beneath the surface.

The Paradox of Choice in Retirement

Unlike traditional roles, Katherine's position has no fixed retirement age. She could continue indefinitely. And that creates a new kind of challenge—the paradox of choice.

If you can keep working… should you?

Rather than choosing between "all or nothing," Katherine is exploring a more nuanced path:

• Reducing from three groups to one
• Staying engaged in meaningful work
• Creating more space for personal life and exploration

This is a powerful reframe. Retirement doesn't have to be binary. It can be designed.

Preparing Before You Retire

Perhaps the most valuable insight Katherine offers is that she has already been preparing for retirement—without calling it that.

She has:

• Structured her own time for years
• Built her identity around relationships, not titles
• Prioritized wellness as a daily practice
• Maintained independence in how she works and lives

As a result, she does not fear the four common retirement pain points:

1. Loss of identity
2. Lack of daily structure
3. Unclear purpose
4. Disconnection from community

Why? Because she has already built a life that isn't dependent on a job to provide those things.

This is the real lesson: Retirement is not something you enter. It is something you prepare for—while you are still working.

Couples, Conversations, and "Confetti Moments"

Another powerful theme in this episode is how retirement impacts relationships at home.

Katherine and her husband are both still active, both thinking about the future—but not always in structured ways. Instead, they have what she calls "confetti moments"—brief, scattered conversations about what retirement might look like.

This is deeply relatable.

Many couples don't sit down and design their future together. They talk in fragments. And yet, retirement will require alignment:

• How will we spend our time?
• Will we keep working?
• What does "being together" actually look like?

Without intentional conversations, these differences can become points of tension.

What This Means for You

Katherine's journey reminds us that retirement is not an ending—it is a transition into a new stage of life that deserves as much thought and care as any career move.

It is not about stopping. It is about redesigning.

Key Takeaways

• Retirement is not a single event—it is a gradual, human transition.
• Leaving work often means leaving relationships, not just responsibilities.
• Organizations must treat retirement as a cultural and strategic issue, not just HR process.
• The best retirement transitions are designed, not abrupt.
• Preparing early—by building identity, structure, purpose, and community—makes all the difference.
• Couples need intentional conversations about what retirement will look like together.
• You don't have to stop working—you can redefine how you work.

Learn more about Katherine Crewe:

Katherine's profile: linkedin.com/in/katherinecrewe

Connect with me:

• Join my Substack Newsletter Rethink Retirement
• Website: www.simonassociates.net
• Book Website: www.andisimon.com
• Email: [email protected]
• Learn more about our books here:
  • Rethink: Smashing the Myths of Women in Business
  • Women Mean Business: Over 500 Insights from Extraordinary Leaders to Spark Your Success
  • On the Brink: A Fresh Lens to Take Your Business to New Heights

Now--it is time to share our new book with you! Rethink Retirement: It's Not The End--It's the Beginning of What's Next

Out on Amazon and WalMart, and in your local bookseller and Rethink Retirement: The Workbook