The Retirement Glide Path – Part 8: The Decision
For the past several weeks, I’ve been writing about my retirement transition as it has been unfolding in real time.
Not in theory.
Not as a plan.
But as a series of questions I’ve been trying to answer honestly:
When is the right time to retire?
How do you finish your career strong?
Who are you without your career?
What will actually give your days meaning?
Over the last week or so, something shifted.
I stopped asking when to retire…
and made the decision.
I’m going to retire.
Why Deciding When to Retire Isn’t Just a Financial Decision
If retirement were purely financial, this decision would have been easy.
We reached “the number.”
The spreadsheets said we were ready.
Our financial advisors confirmed it.
From a financial independence standpoint, the path was clear.
But as I’ve come to realize, deciding when to retire is rarely about money alone.
It’s about timing.
Identity.
Responsibility.
And how you weigh what you’re gaining against what you’re leaving behind.
The Forces Pulling in Both Directions
Even as I approached this decision, there were strong arguments on both sides.
On one side:
More time with my wife
More flexibility in how I spend my days
The opportunity to step into the next chapter together
A growing awareness of how quickly time passes—and what we’ve seen in our own family histories
On the other:
A role where I’m still contributing at a high level
A team and organization that value my work
A program I care about that is still taking shape
The financial benefits of continuing to work—including income and subsidized healthcare
None of those things are trivial.
That’s what made this decision so difficult.
The Conversation That Made It Real
A couple weeks back, I had a conversation with my boss.
I told him I was considering retiring soon—possibly as early as June 5.
He didn’t love the idea.
And in some ways, that was reassuring.
It meant the work I’ve been doing matters.
It meant I wasn’t just fading out unnoticed.
He asked if I would consider staying longer—potentially through February 2027—to help get the program fully established.
It was a reasonable request.
One that I took seriously.
I even negotiated in a few perks that made it more desirable to stay—shorter work weeks, more flexibility to take time off.
All of this made the decision more complex, not less.
The Financial Reality of Continuing to Work
There was also a very practical side to the decision.
Continuing to work would mean:
More income
More time to strengthen our financial position
And continued access to employer-subsidized healthcare
That last one carries real weight.
Stepping away means stepping into a different cost structure—at least until Medicare becomes available.
Every additional month of working improves the financial picture.
There’s no question about that.
But it also raised a question I couldn’t ignore:
At what point does more financial security begin to cost something else?
I had a conversation with a retired friend about this. He asked how I could consider retiring when the economy feels uncertain.
I told him something I’ve come to believe through studying retirement:
It’s rare for people to look back and wish they had worked longer.
Far more often, they wish they had retired sooner.
What Finally Shifted
In the end, the decision didn’t come down to a single moment or conversation.
It came from a growing clarity.
A realization that kept surfacing, no matter how I looked at it:
We don’t get this time back.
Not the healthy years.
Not the window where we have both the freedom and the ability to fully live this next chapter together.
My wife has already stepped into retirement.
She’s gotten a glimpse of what life could look like.
And through her eyes, I’ve started to see it more clearly, too.
This isn’t just about leaving work.
It’s about stepping into something we’ve been moving toward for years.
And at some point, continuing to delay that step—even for good reasons—started to feel like a trade-off I didn’t want to keep making.
The reality is, none of us knows how much time we have left. Both my wife and I have moms who died in their 70s from health issues. Even before that, their failing health effectively ended their and their husbands’ plans for fun and adventure in retirement.
This is the question I couldn’t escape: Is it worth trading 8 months of our healthy years—our so-called “go-go years”—when we are healthy and fit enough to start trampling all over our bucket list for a few more paychecks?
Viewing it that way, the answer became obvious.
What Didn’t Decide It
Interestingly, there were things that didn’t make the decision for me.
It wasn’t:
A perfect financial model
A moment where everything felt completely certain
A loss of interest in my work
Pressure from anyone else
If I had waited for complete clarity, I would probably still be waiting.
Leaving Well Still Matters
Deciding to retire doesn’t mean abandoning everything I’ve been part of.
Finishing strong still matters to me.
Being dependable still matters.
Honoring commitments still matters.
But I’ve come to see that finishing strong doesn’t always mean staying as long as possible.
Sometimes it means leaving at the right time—and doing it thoughtfully.
What I Still Don’t Know
I don’t have everything figured out.
I don’t know exactly what each day will look like.
I don’t know how quickly new rhythms will form.
I don’t know how my sense of identity will continue to evolve.
But I’m okay with that.
Because waiting until every unknown is resolved is just another way of not moving forward.
As the saying goes, not to decide is to decide.
Waiting is still a choice, and not always a good one.
Stepping Into What’s Next
What I do know is this:
I’m not running away from anything.
I’m stepping into something.
More time with my wife
More presence in the relationships that matter most
More space to pursue purpose, not just productivity
That doesn’t mean every day will be perfect.
But it does mean the days will be ours.
An Invitation
If you’re wrestling with the decision of when to retire, you’re not alone.
You may already be financially ready.
And yet still unsure.
Still weighing.
Still asking:
“Is this the right time?”
There may not be a perfect answer.
But there may be a moment when the question shifts from:
“Could I stay longer?”
To:
“Why am I still waiting?”
For me, that shift finally happened.
And it moved me from thinking… to acting.
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
Part 8 – The Decision
