I’ve been saying I retired from medicine in 2018 for years now. It’s become a kind of shorthand, an easy way to explain a much more complicated reality.
And yet, if I’m being honest, the statement has always felt a little slippery. It never fully lands. Because the truth is, I still practice hospice medicine occasionally. I host a podcast. I write. I speak. Some of these things even pay me.
So am I retired? Or am I just someone who changed careers and prefers a more flattering label?
I’ve gone back and forth on this for years. And the more I’ve thought about it, the more I’ve realized the problem isn’t really about me at all. It’s about the way we define retirement. Or more accurately, the way we don’t define it very well.
We talk about retirement constantly—plan for it, dream about it, chase it—but we rarely stop to ask what it actually means. When you strip everything down, it seems to revolve around two fundamental forces: time and money.
The issue is that we’ve never quite figured out how those two interact. Sometimes we lean heavily on time. Other times we focus almost entirely on money. But we rarely hold both ideas together in a way that feels clean or satisfying.
That’s where the confusion begins.
In the old world, retirement was simple, almost overly so. It had nothing to do with money. It had everything to do with time.
If you woke up every morning and went to a job, especially one where someone else dictated your schedule, you weren’t retired. It didn’t matter how much money you had. You could have more than enough to live comfortably for the rest of your life, but if you were still showing up to work, we wouldn’t call you retired.
On the flip side, if you stopped working, you were retired. It didn’t matter if that decision was intentional or forced. It didn’t matter if you had the financial means to support yourself or not. If you weren’t working and no longer looking, you were retired.
In this framework, retirement was defined entirely by how you spent your days. It was visible and easy to categorize, which made it convenient. But it also missed something important…something deeper than just how we fill our hours.
Then came the financial independence movement, and we tried to fix that gap.
Instead of focusing on time, we shifted the conversation toward money. Retirement became less about what you were doing and more about what you could do.
We started talking about “the number.” That magical point where your investments could support your life indefinitely. Two million, five million, whatever framework you use: the 4% rule or some variation of it.
If you hit that number, you reached financial independence. And if you reached financial independence, you could retire.
But notice something subtle here. We didn’t actually redefine retirement, we just layered a new definition on top of the old one. Because even after hitting that number, we still hesitate.
We still ask the question: But are you actually retired?
And almost immediately, we drift back to time. If you’re still working full-time, we hesitate to give you the label. If you’re not working, we embrace it more easily.
We’re caught between two competing definitions, and they don’t quite reconcile.
So here’s the idea I keep coming back to.
What if retirement has nothing to do with how you spend your time?
What if we define it entirely by money. Not in a superficial way, but in a structural one?
What if retirement is simply the moment your assets are large enough that you can begin to spend them down (ie decumulate) and reasonably expect that they will last for the rest of your life?
That’s it. No lifestyle audit. No judgment about whether you’re working too much or not enough. Just a number.
Because when you hit that number, something fundamental shifts. You gain control.
When you have enough to decumulate, your relationship with time changes in a way that’s hard to fully appreciate until you experience it.
Work is no longer a requirement. It becomes a choice.
And that distinction, between obligation and choice, is everything.
You can continue doing exactly what you were doing before. Same job, same hours, same responsibilities. From the outside, nothing appears to have changed. Your life might look identical.
But internally, the experience is completely different. Because now you’re choosing it.
And that’s the piece we tend to overlook.
We look at someone who reaches financial independence and keeps working, and we say, “Well, they’re not really retired.”
But maybe they are.
Maybe they’re just someone who has chosen to spend their retirement doing the same thing they were doing before. It sounds contradictory at first, but it starts to make sense when you examine the motivation behind the action.
If you no longer need the paycheck—if your survival isn’t tied to your work—then what is work, really?
It begins to resemble a hobby. A serious hobby, perhaps. One that carries responsibility, structure, and even financial reward. But at its core, it’s still something you’re choosing to do.
And that’s the dividing line.
The mistake we often make is assuming that retirement should look a certain way. We picture freedom in very specific terms like travel, leisure, slow mornings, and unstructured days.
And for some people, that’s exactly what retirement becomes.
But for others, it looks surprisingly similar to what came before. They keep building, creating, and contributing. Not because they have to, but because they want to.
The difference isn’t what they’re doing. It’s why they’re doing it.
When I left my full-time job in medicine, I expected retirement to feel like an ending. A clean break. A closing of one chapter before moving into something entirely different.
But that’s not what happened.
Instead, it felt like a shift. I didn’t stop working. I just started working on things that felt more aligned with who I was becoming. Hospice. Writing. Podcasting. Speaking.
If you looked at my calendar, you might say, “This doesn’t look like retirement.” And using the traditional definition, you might be right.
But if you look at it through the lens of having enough, a different truth emerges.
I’m not working because I need to. I’m working because I choose to.
And that distinction shifts everything.
So maybe it’s time to simplify this whole conversation.
Maybe retirement isn’t about crafting the perfect lifestyle or achieving some idealized version of freedom. Maybe it isn’t even something that’s visible from the outside.
Maybe it’s just a number.
The moment you have enough. The moment you can stop, even if you decide not to.
Everything that comes after that point: how you spend your time, what you choose to pursue, what you walk away from…that’s something else entirely.
That’s not retirement.
That’s freedom.
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Thought provoking essay, thanks!
When I broached the idea of retiring young-ish with my wife, she pushed back a little… ok, but you need to find something productive to do. Retirement can’t be just sitting on the couch and withering away.
Fair enough.
I know I’ll be very busy writing and speaking and investing my time in people. Because I’m already moving in that direction. I have a plan.
But most people don’t have a healthy plan for retirement. Maybe travel. Or, if they’re near family, babysit grandkids. That’s the extent of what I usually hear. I think everyone should make an intentional plan, starting a couple years before they get to financial independence.
If the plan is to keep working at the same job, I’d ask why? If it’s a place that helps your life feel more meaningful, great. But, too often, our role becomes wedged into our identity so strongly that we just don’t know who we’d be without it. Not a healthy reason to keep working.
This may just be me, but I’ve noticed the word “retirement” has shifted in meaning over time.
In the middle of my career, retirement felt like something to look forward to. It was all about freedom, more time, and a reward for working hard and saving.
Now that I’m actually retired, I still stay active and spend my time on meaningful things, but the word itself feels different. It carries a subtle negative connotation, like I’ve stopped being productive or I’m somehow slowing down.
Words matter to me because they elicit feelings. And it’s interesting how “retirement” used to feel energizing, but now feels like a bit of a letdown in a weird way.
Maybe I’m splitting hairs, or maybe it’s just my way of processing getting older. I find it fascinating how the same word hits me so differently now than in my younger years.