Between Who You Were and Who You’re Becoming
I asked a simple question of those joining me for tomorrow’s webinar:
What’s on your mind as you think about retirement?
What came back wasn’t simple at all.
It wasn’t a neat list of goals or financial concerns.
It was something far more human—full of curiosity, excitement, uncertainty… and, in some cases, a quiet sense of loss.
As I read through the responses, I realized I wasn’t looking at one group of people.
I was looking at three very different journeys.
1. Those in Transition
Some are already stepping away from their careers—or standing right at the edge of that decision.
They’re asking:
Who will I be without my work identity?
How do I reinvent myself?
What does a life look like that is open-ended?
There is excitement here. But also uncertainty.
Anthropologists have a word for this stage: liminality—the space between what was and what will be.
It’s where transformation happens.
It’s also where people can feel most unmoored.
2. Those Still Working (But Thinking Ahead)
Others are still fully engaged in their careers, but something has shifted.
They’re beginning to ask:
How will I plan my days?
What will give me structure?
What dreams have I postponed?
Many described themselves as “somewhat confident”… and at the same time, unsure.
They’re not retiring yet.
But they’re already sensing that this next phase will require something different from them.
Not just planning—but reimagining.
3. Those Already Retired
And then there are those who have already made the transition.
Some are thriving.
Others are asking deeper questions than they expected:
How do I make sure I’m not just filling time?
I don’t want busy work—I want to make a difference.
How do I stay connected?
A few spoke candidly about a sense of loss they hadn’t anticipated.
They did everything “right.”
And yet, something feels unfinished.
What I Saw Across All of Them
While their situations differ, the themes were remarkably consistent.
People are not just asking about retirement.
They are asking about:
Identity — Who am I now?
Purpose — Where do I still matter?
Structure — How do I shape my days?
Community — Who is on this journey with me?
One person captured it beautifully:
“Why do we think that so often our identity is who we were when working? Aren’t we all so much more?”
Yes. We are.
But we’re not always prepared to live that truth.
The Tension No One Talks About
What struck me most wasn’t fear.
It was the contradiction.
People feel:
Blessed… and uncertain
Excited… and questioning who they are
Free… and unsure how to use that freedom
We’ve done a very good job preparing people financially for retirement.
We’ve done far less to prepare them humanly.
A Different Way to See Retirement
We’ve been taught to think of retirement as an ending.
But what these responses show—clearly and powerfully—is something very different:
Retirement isn’t an exit.
It’s a transition into a life that hasn’t yet been designed.
And like all transitions, it requires more than a plan.
It requires reflection, experimentation, and, often, a willingness to sit in the unknown for a while.
Let’s Continue the Conversation
On Tuesday, we’re not going to talk about retirement as a checklist.
We’re going to explore it as a lived experience—through stories, shared questions, and the wisdom of those who are already navigating this path.
If these questions resonate with you, you’re not alone.
You’re right on time. We have a nice community of curious people coming together.
Join me for the conversation. Register here, and even if you cannot join us we can send you the video.