In this episode of the Earn and Invest podcast, I do something I’ve been doing more often lately—I pause.
No guest. No back-and-forth conversation. Just me, sitting with my thoughts.
I’m recording at 5:00 AM from a beach in Cabo, the light just starting to come up. I’m fresh off speaking about purpose at the EconoMe conference and death and dying at the White Coat Investor conference. And somewhere between those two topics—purpose and mortality—I find myself reflecting on something more personal:
What the last eight years of retirement have actually felt like.
Not the idea of it. Not the plan.
But the lived experience.
Back in 2018, I stepped away from full-time medicine, shifting my focus mostly to hospice work and the parts of life that felt more aligned—writing, podcasting, connecting.
At the time, like many of us would, I had questions.
Would I have enough money?
Would I still feel relevant?
Would my days feel full… or empty?
Eight years later, I have some answers. Not in the form of a blueprint, but more like a collection of realizations and things I couldn’t have fully understood until I was living them.
The first is almost disorienting in its simplicity:
Life is better than I thought it would be.
There’s a lightness to the way my days feel now. I wake up excited more often than not. There’s very little I dread. And maybe most importantly, I have full control over my time.
That control seems to change everything.
And yet, it’s not like ambition disappeared.
I still set goals. I still create. I still push myself: whether that’s publishing books or chasing fitness milestones.
But the emotional weight of those goals has shifted.
They’re no longer tied to my identity or self-worth. They don’t feel urgent or heavy. Instead, they act more like guideposts…something to move toward, without the pressure of needing to arrive.
One of the more surprising things is that my life is still busy.
Full, even.
My days are packed with writing, podcasting, conversations, and projects. But the feeling underneath that busyness is completely different than it used to be.
Before, there was always a sense of scarcity. Not enough time. Not enough space. Not enough room to breathe.
Now, even with a full calendar, there’s an underlying sense that there’s enough of everything.
The same activity. A completely different experience.
Relationships, too, have shifted in a way I didn’t expect.
I actually have more friends now than I did while working.
But they’re different kinds of friendships. Less circumstantial, more intentional. Built through shared interests, online communities, conferences—connections that span geography but feel surprisingly close.
Without the built-in social structure of work, I’ve had to create connection more deliberately. And in doing so, it’s become more meaningful.
Not everything fits neatly into a single narrative, though.
In one breath, I’ll admit I’ve become less organized and increasingly resistant to a packed calendar. Where I once thrived juggling ten responsibilities at once, now even a handful of scheduled commitments can feel like too much.
I find myself drawn to what I think of as “uncalendared work”—the ability to wake up and choose what to focus on based on energy and curiosity rather than obligation.
And yet, almost in contradiction, I also notice how much I value routine.
Simple, grounding rituals. Morning coffee. A workout. One or two anchor points in the week—like a hospice meeting—that give structure without overwhelm.
It’s less about scheduling everything, and more about having just enough rhythm to feel steady.
Time itself starts to feel different in this kind of life.
The old boundaries, weekdays and weekends, work and vacation, begin to dissolve.
I can record a podcast from a beach in Cabo or spend a quiet afternoon at home doing nothing in particular. It all blends together in a way that feels less segmented and more fluid.
Less like balancing different parts of life.
More like just… living it.
Maybe the most personal realization is this:
I feel more like myself than ever before.
Without the constant pull of external expectations, my days are filled with what I think of as “identity-consistent” activities—creating, connecting, thinking, exploring.
Not things I have to do.
Things that feel like a natural extension of who I am.
And in that, there’s a kind of ease that’s hard to manufacture any other way.
Of course, money doesn’t disappear from the picture entirely.
I still think about it. I still pay attention.
But the emotional charge around it has faded significantly.
Over the past eight years—through a pandemic, a major home remodel, and my wife retiring—I’ve grown comfortable with the idea of spending, of de-cumulating, of actually using the resources I spent so long building.
The anxiety that once surrounded money has softened into something quieter. More manageable.
And then there’s the question I know a lot of people wrestle with when they get close to this point:
Would I ever go back?
For me, the answer is clear.
I can’t imagine working in the same way if I didn’t have to. The freedom I have now—the ownership of my time—feels too valuable.
In fact, I’ll admit something that many people quietly suspect:
I wish I had done it sooner.
In the after-show, I touched on an idea I’ve been thinking about lately—that retirement isn’t some distant milestone you cross when you stop working entirely.
It begins the moment you have enough.
Enough to choose.
Enough to walk away.
Enough to know that your time is, in some meaningful way, your own—even if you decide to keep your job.
There’s a moment where I responded to a listener whose spouse worries that early retirement might lead to a lack of productivity.
It’s a common fear.
And my response is simple:
Maybe the goal isn’t to stay productive.
Maybe it’s to stay purposeful.
Another listener mentioned that the word “retirement” itself has started to feel heavy. Final. Almost like a slowing down.
I wonder if that feeling comes from something deeper—this persistent cultural pressure to keep achieving, to keep proving, to keep moving forward in visible ways.
But what if retirement isn’t about stepping back?
What if it’s about stepping into something else entirely?
Something more spacious. More intentional. Maybe even more alive.
Eight years in, I don’t think of retirement as perfect.
But it does feel real.
Less like an escape.
More like a different way of being.
Hi Jordan, I’m also an MD. Can you talk about how you structure your hospice work to allow such flexibility in your schedule? Is it a 1099 or part time W2 position? Do you work the same days each week? Can you do this work remotely? Do you have coverage if you are traveling? Thanks.
I am 8 months in. Your thoughts are very close to my own. I particularly agree with your comments about productivity. I am loving having the temporal, mental, psychological space to see- to establish - who I am.