What happens when retirement doesn’t feel like freedom?
Recently, I had the pleasure of sitting down with Andrea Simon, the author of Rethinking Retirement for a candid Substack video conversation about what really happens when we step away from our careers—and why so many people find themselves unprepared for what comes next.
Our conversation wasn’t theoretical. It was deeply human.
The Gap No One Talks About
In Andi’s work as a corporate anthropologist, she has spent time living inside senior living communities, observing what people say—and what they feel.
What she found was striking.
Many residents had done everything “right”:
They saved well
They planned financially
They reached retirement successfully
And yet, something was missing.
They felt disconnected.
Unheard.
Uncertain about their purpose.
As Andi and I explored together, retirement is not simply a financial milestone—it’s a profound identity shift. And most people are not prepared for it.
Retirement Is Not an Exit—It’s a Transition
One of the most important ideas we discussed is this:
Retirement isn’t about stopping. It’s about becoming.
Andrea described how many people approach retirement as if it’s a problem to solve:
“What do I do now?”
But the real question is:
“Who am I now—and who do I want to become next?”
Without intention, people often fall into one of two traps:
They drift, unsure how to structure their days
Or they recreate their old work life, just in a different form
Neither leads to fulfillment.
The Missing Piece: Structure, Purpose, and Community
Both of us see the same patterns again and again.
When people leave their careers, they don’t just lose a job. They lose:
Structure
Identity
A sense of mattering
A built-in community
And yet, few organizations—or individuals—plan for this.
Andi shared a powerful framework: treat retirement like you would any major strategic initiative.
Test ideas.
Experiment.
Adjust.
Design your next chapter, don’t stumble into it.
What Companies Are Missing
There’s another dimension we explored that often goes unnoticed:
Organizations are not ready for retirement either.
Too often, retirement is treated as a one-and-done event:
A farewell
A cake
And then… silence
But what’s lost is enormous:
Institutional knowledge
Relationships
Mentorship
Continuity
We discussed the opportunity for companies to rethink this entirely:
Phased transitions
Alumni networks
Ongoing contribution models
Not only does this support those leaving—it strengthens those who remain.
So, What Should You Do?
If you are approaching retirement—or already there—this is your moment to pause and reflect.
Ask yourself:
Where do I still want to matter?
What would a “good day” look like for me now?
Who will I spend time with—and who needs me?
Because this stage of life is not about winding down.
It’s about reimagining what’s possible.
Watch the Conversation
I invite you to watch the full conversation nd reflect on your own next chapter.
And if this resonates, stay with us.
This is just the beginning of a larger conversation—one we need to have together.
