Retirement: What Reinvention Really Looks Like
Notes from the field that enlighten us
We often talk about retirement as if it’s a destination.
But in truth, it’s something else entirely.
It’s a transition.
A liminal space.
A moment when the old identity no longer fits—and the new one hasn’t fully formed.
Over the past few weeks, I’ve had the privilege of speaking with two remarkable women on On the Brink with Andi Simon podcast who are not just talking about retirement—they are living its reinvention.
Each are taking a different path.
Each faces different uncertainties.
But both are helping us see what’s possible when we let go of the idea that retirement is an ending.
Louise Olson: Finding Meaning Beyond the Expected
I met Louise through the Lustre community—an emerging network of women who are asking deeper questions about what comes next.
Louise’s story is not about “retiring” in the traditional sense.
It’s about stepping into a phase of life with curiosity rather than fear.
She reminds us that reinvention isn’t a single decision. It’s a series of small, often uncertain steps toward something that feels meaningful.
There’s a quiet courage in her journey—one that many of us recognize but don’t always name.
You can listen to Louise’s story here:
https://www.simonassociates.net/474-the-greatest-lessons-on-reinvention-and-retirement-from-louise-olson/
Jeannette Hobson: Designing a Life, Not Just Leaving a Career
Jeannette’s story is one I know more intimately—she is one of the women featured in Rethink Retirement.
What makes her journey so powerful is that she approached retirement not as a withdrawal, but as a design challenge.
Who do I want to be?
How do I want to spend my time?
Where do I still matter?
She didn’t wait for the answers to appear. She actively built them.
Her story reminds us that retirement is not something that happens to us—it’s something we can shape, intentionally.
You can listen to Jeannette’s conversation here:
https://www.simonassociates.net/rethink-retirement-with-jeannette-hobson/
What These Stories Teach Us
Across both conversations, a few themes keep surfacing:
Reinvention is not linear. It’s messy, iterative, and often uncomfortable.
Identity doesn’t disappear—it evolves.
Structure matters more than we expect. Empty calendars can feel liberating… and then disorienting.
Purpose is not something you find once. It’s something you keep building.
Most importantly:
You are not alone in wondering what comes next.
A Thought to Sit With
If retirement is not an ending…
Then what are you beginning?
If these stories resonate, I’d love for you to join me for a deeper conversation in the upcoming Masterclass on June 2nd, where we’ll explore how to design your next chapter with intention. Check it out here: https://www.andisimon.com/workshops/