When Is the Right Time to Retire?

Reflections on this "big" question

After I published my recent Substack essay, When Every Day Becomes Saturday, many readers reached out with a deeper question:

“How do you know when it’s actually time?”

The truth is, there is no universal answer.

Some people retire because they are exhausted.
Some because a company restructures.
Some because their spouse is ready.
Some because their bodies begin whispering — or shouting — that life cannot stay at this pace forever.

And some never truly retire at all.

As my husband Andy and I continue working, speaking, writing, and building new ideas together, I often reflect on our own reluctance to “retire” in the traditional sense. My husband sold his company and joined mine. Instead of slowing down, we redesigned our lives. Not because we fear stopping, but because purpose still pulls us forward.

In researching Rethink Retirement, I found that the people who navigated this transition best did not focus primarily on leaving work. They focused on moving toward something meaningful.

Take Gordon Bernhardt. After more than 30 years building an ethical financial advisory firm, he sold his company not to maximize his personal payout, but to protect his clients and team.

At first, Gordon imagined he would continue working much longer. But gradually, after walking the Camino de Santiago and reflecting deeply on what mattered most, he realized something profound: timing was not about squeezing every last professional achievement from life. It was about aligning his life with his values.

Retirement, for Gordon, became the gift of presence.

Then there is Pat Shea, whose story could not be more different. Pat has “retired” multiple times — from corporate America, nonprofits, technology startups, and leadership roles — only to reinvent herself again and again.

For Pat, retirement is not an ending. It is a pause. A recalibration. A space to breathe before asking: What now calls me forward?

At 66, she is increasingly aware that time matters. Her husband wants to travel. Family matters more. Fifty-hour workweeks no longer hold the same appeal. Yet she insists she is not retiring from purpose itself.

That distinction feels important.

Perhaps the question is not:
“When should I retire?”

Perhaps it is:
“What kind of life do I want now?”

Edie Fraser, my dear friend and collaborator, who wrote the forward to this book, often says she is not retired — she is “repurposed.” That single word captures what I see happening all around me. Edie continues building organizations, mentoring entrepreneurs, supporting women leaders, and creating impact because purpose has never had an expiration date for her.

And honestly, many of us no longer fit the old retirement story.

We are healthier longer.
We are living longer.
We are still curious.
Still contributing.
Still becoming.

What I have learned as an anthropologist studying this transition is that retirement is not really about age. It is about identity, structure, purpose, and community. When one chapter closes, another must consciously be created.

Otherwise, every day really does become Saturday.

And while that sounds lovely at first, eventually most humans need more than leisure. We need meaning. We need connection. We need to know that who we are still matters.

So perhaps the right time to retire is not when society says you should.
Not when the calendar says you are old enough.
Not even when the money says you can.

Perhaps it is when you are ready to redesign your life around what matters most now.

I suspect Andy and I are still figuring that out ourselves.

I would truly love to hear from you.

Have you retired and loved it?
Retired and struggled with it?
Un-retired?
Repurposed yourself?
Or are you, like Andy and me, still rethinking what retirement even means?

What surprised you most once work no longer structured your days?

And perhaps the deeper question is this:

Have we outgrown the old idea of retirement altogether?

Maybe retirement is not really the point anymore.

Maybe the real challenge is:
How do we continue to live lives filled with meaning, contribution, curiosity, connection, and joy as we age?

What has this chapter taught you about yourself?

I would love to hear your story.