Not Retired Yet: My Life in The Villages at 40-something
Unexpected Lessons From America's Most Misunderstood Community
When I told coworkers and friends I was moving to The Villages — a sprawling retirement town in central Florida with over 150,000 residents — they didn’t quite know what to make of it.
Some raised eyebrows. Others made jokes. Most just asked: “Why?”
A Different Kind of Move
My reasons were personal, practical, and professional.
My 70-year-old dad was in the process of moving there. My sister was considering it too. After twenty years living in different states, it felt like the right time to reconnect with them, especially after my mom’s recent passing.
Florida made sense for other reasons. Better weather for training in the winter since I compete in Masters Track & Field. No state income tax. The chance to escape Chicago winters. Plus, the real estate play was smart.
We didn’t move into one of the traditional villages, though. My wife and I chose Middleton by The Villages. It’s a newer, multi-generational neighborhood that’s part of the larger development. It keeps us within The Villages’ vibrant community, while adding its own emerging energy and mix of residents. And we benefit from access using our in-area guest ID cards thanks to my dad.
There was one bonus. My work in user experience (UX) design had been leading me deeper into researching how older adults engage with digital experiences. Living here gives me firsthand insight into what matters, what frustrates, and what works. This affords me the opportunity to learn directly from the people who are shaping the future of aging.
Based on all that, we made The Villages our primary residence and enjoy the benefits of snowbirding.
Now, I expected leisure. I expected golf carts. I expected early dinners. The typical assumptions about what older adults do on a daily basis in a place like the world's largest retirement community.
What I didn’t expect was what actually happened.
What Shocked Me Most
I joined The Villages Track & Field Club. Partly to train. Partly to meet people.
That’s where the surprise hit me.
Here were men and women in their 60s, 70s, even 80s, training as elite athletes. Not just for fitness — but to compete. They were dedicated and deeply informed about sprint mechanics, recovery, and performance.
These weren’t people “winding down.” They were ramping up. And they welcomed me, not as an outsider, but as a fellow athlete. It shifted my mindset about training and aging.
Retirement Isn’t What We’ve Been Told
The truth is, we’ve been sold a narrow and sorely outdated vision of retirement. Here’s what's really happening in America’s longevity economy.
In a notorious place like The Villages, there are vast amounts of stereotypes surrounding this community. To be fair, some of the stereotypes do show up.
Yes, there’s lots of golf.
Yes, there are social clubs for every imaginable hobby.
Yes, there’s even a certain Florida vibe that’s easy to caricature.
But that’s not the full story.
Most of the people I’ve met here aren’t just looking to pass the time. They’re building something new with intention. They’re focused on community, purpose, and contribution. Not just leisure.
They’re not in decline. They’re in transition.
And they’re making the most of it.
It’s not just inspiring. It’s instructive.
Lessons from the So-Called “Retired”
Here are a few things I’ve learned since being here:
1. People aren’t retiring, they’re repurposing. Many are on their third or fourth act. They’re launching businesses, volunteering, and mastering new skills.
2. Community is a daily practice. From walking clubs to wine nights, the social fabric is strong. People here don’t isolate — they participate.
3. Aging isn’t a fade to black, it’s a spotlight. I’ve met people who are more alive in their 70s than some I know in their 30s. There’s a level of energy, curiosity, and generosity that isn’t talked about enough.
4. The experiment is spreading. I’ve met Gen Xers similar to myself (a Xennial), working remotely while enjoying a slower pace. Some are thriving. Others are figuring it out. But we’re all learning what the future of “retirement” might really look like.
Still Curious?
I didn’t expect to find role models here. But I did. And it’s changed how I think about aging, ambition, and what it means to live well at any age.
Have you ever had an experience that completely flipped your assumptions about aging or where you thought you’d live?
Until next time,
Rethink Aging With Us
This is for you:
If you're in your 30s, 40s, 50s, or beyond and not ready to fade out.
If you're a builder, strategist, or decision-maker trying to understand what aging really means for your product, team, city, or community.
If you're tired of “decline narratives” about age and are ready for something more honest, more useful, and more human.
Join other curious and forward-thinking people who are reconsidering what older age can be — and how to live it with intention.
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I remember a friend (in his 70s at the time) who said he'd never move to a "retirement" community because why would he only want to be around people over a specific age? He stayed as long as he could in his home in a vibrant neighborhood with people of all ages. I'm happy to see the trend is starting to shift a little. Thanks for sharing your take on this with us. Looking forward to reading more of your work.
I was just hearing about The Villages. My husband are I looking into Active 55 communities and a friend sang the jingle. We heard another such community near Knoxville.
But neither is near our grandson. For now, we stay put.