The Retirement Glide Path – Part 7: Navigating the Conversation
Last week, I had a conversation that made the retirement transition feel very real.
I told my boss I was considering retiring soon—possibly as early as June 5.
He didn’t love the idea.
And honestly… that was good to hear.
Because one of the most difficult parts of deciding when to retire isn’t financial—it’s knowing what to do when people still need you.
When Someone Still Needs You
There’s something affirming about hearing that your presence still matters.
That your work is valued.
That your contributions aren’t easily replaced.
In some ways, it’s exactly what you hope to hear after years of showing up and doing your best.
But it also complicates the retirement decision.
Because now the question isn’t just:
Am I ready to retire?
It becomes:
What is the right way to leave? When is the right time?
The Retirement Conversation
When I shared my thoughts, my boss asked a simple question:
Would I consider staying longer?
Not indefinitely.
Not even for years.
But long enough to help get the program I’m leading fully off the ground—potentially through February 2027.
It wasn’t a demand.
It was a reasonable ask.
And that’s what made it harder.
The Tension in the Retirement Transition
This is where the retirement transition becomes real.
Because now, I’m holding two things at the same time.
On one hand:
A growing desire to step into the next chapter
More time with my wife
More flexibility in how I spend my days
On the other:
A commitment to finish what I started
A desire to leave well
A recognition that my work still matters
Neither side is wrong.
That’s what makes deciding when to retire so difficult.
The Financial Side of Retiring vs. Continuing to Work
There’s also a practical layer to this decision that I can’t ignore.
Continuing to work a little longer doesn’t just mean more time in the role—it also means continued income, continued contributions to our portfolio, and something that carries more weight than I might have appreciated in the past:
Healthcare coverage.
Right now, a significant portion of our healthcare costs is subsidized through my employer. Walking away from that means stepping into a very different reality—one that likely involves higher out-of-pocket costs, at least until Medicare becomes available.
That doesn’t mean the decision should be driven entirely by finances.
But it does mean the financial implications are real.
Every additional month of working strengthens the financial side of the equation:
A little more margin
A little more flexibility
A little more buffer against the unknown
At the same time, it raises an important question in retirement planning:
At what point does “more security” start to cost something else?
Financial security matters—but so does the time you’re securing it for.
Not Just Whether to Retire—But How to Transition
As I’ve been thinking about it, I’ve realized something:
This isn’t just a question of whether I retire.
It’s a question of how I transition.
If I do extend my timeline, it likely won’t look exactly like the past.
I’m beginning to consider what it might mean to:
Work slightly shorter weeks
Build in planned time off
Allow for more flexibility—occasionally stepping away when life calls for it
Not as a way of easing out irresponsibly…
But as a way of transitioning into retirement intentionally.
Redefining the Retirement Glide Path
Up until now, I’ve thought of the retirement glide path mostly in terms of timing.
When do I retire?
How do I finish strong?
What comes next?
But this conversation introduced a new dimension.
The retirement glide path isn’t just about the end date.
It’s about the shape of the time leading up to it.
Finishing Strong Before Retirement
In the last post, I talked about finishing strong before retirement.
This feels like a continuation of that idea.
Because finishing strong doesn’t necessarily mean leaving as soon as you can.
And it doesn’t mean staying as long as someone asks you to.
It means finding the balance between:
Honoring your commitments
And honoring the season you’re stepping into
That balance is rarely obvious.
Still Deciding
I don’t have a final answer yet.
I’m still thinking.
Still talking it through with my wife.
Still weighing what matters most.
What I do know is this:
The decision feels different now than it did a week ago.
Not because anything changed financially.
But because the human side of the retirement decision came into focus.
An Invitation
If you’re approaching retirement, you may find yourself in a similar place.
You may be ready to step away…
And yet aware that people still depend on you.
You may feel the pull toward what’s next…
While also feeling the weight of what you’re leaving behind.
So maybe the question isn’t just:
When should I retire?
But:
What does it look like to leave well—when staying a little longer still serves a purpose?
The Retirement Glide Path Series
Part 1 – One Couple, Two Timelines
Part 2 – One Couple, Two Timelines, Different Speeds
Part 3 – Wrestling With Timing and Identity
Part 4 – Leaving Well
Part 5 – Redefining Identity Beyond Work
Part 6 – Moving Beyond Hobbies to Meaning
Part 7 – Navigating the Conversation
