Rethinking Where and How We Grow Older
A Tale of Two Communities
Personal note: I hope you’re enjoying some time with family and friends this holiday weekend. I’d like to welcome over a hundred new subscribers this week! I appreciate you coming along with all of us on this journey to reconsider what older age can be — and how to live it with intention.
I’ve written quite a bit about life as a 40-something living in The Villages since it’s a key part of my story. But I haven’t shared too much about the other place I enjoy living during the summer months.
That’s my home in West Suburban Chicago. A town called Wheaton, Illinois.
In downtown Wheaton, I live in a mid-rise where most of my neighbors are over 50. By October, many (including my wife and I) disappear, heading south for the winter. The halls go quiet.
By November, I’m sprinting on a track under the Florida sun training with members of The Villages Track & Field Club. Many are in their 60s, 70s, and 80s, pushing themselves through drills with the kind of focus you’d expect from college athletes.
Each community is designed around aging — but with very different concepts about what later life should feel like. And I’ve got an interesting perspective being someone who lives in these two different environments.
Different Answers to the Same Question
Downtown Wheaton has mid-19th-century railroad roots and a walkable downtown. The streets are lined with mature trees and older homes. You can walk to the post office, the library, plus several restaurants and coffee shops. Many residents have lived here for decades. Some, like my neighbors and I, head to warmer places each winter. The town values continuity, routine, and self-reliance.
The Villages, in contrast, is a purpose-built community in Central Florida with more golf carts than cars and a calendar that overflows with events. It doesn’t try to preserve the past. It’s designed for constant engagement — sports leagues, live music, group classes, volunteer roles, and entrepreneurial endeavors. The whole place moves. Not at the same pace as youth culture, but with the same momentum.
Spending part of the year in each place gives me a clear view of what works, what’s missing, and what aging really looks like when the environment is designed for more than just maintenance.
5 Things These Contrasting Communities Reveal About Aging
1. Walkability vs. interaction
Downtown Wheaton offers classic walkability. You can reach the grocery store, library, and coffee shops without a car. Sidewalks and tree-lined blocks create a sense of order and calm. You’re near a commuter train line to Chicago and close to the respected cultural institutions of America’s third largest city. You can live your life without depending on a car. It’s easy to be independent. But independence isn’t the same as connection. Most days, that walk happens alone. Inside my mid-rise, social life doesn’t emerge organically. Especially in winter, the building gets quiet.
The Villages, on the other hand, is built for interaction. Social interaction is baked into the design. You’re nudged toward participation — whether it’s a rec center activity, a club meeting, or just waving to neighbors on a golf cart ride. Everything invites you to show up. The layout, the culture, the rhythm of the place. You don’t go weeks without seeing neighbors. You’d have to try.
Takeaway: Access doesn’t equal engagement. Communities have to invite people out, not just let them in.
2. Stability vs. reinvention
Downtown Wheaton values continuity. Many residents have lived in the same home for decades. Aging here often means doing the same things, in the same place, with the same routines. There’s comfort in that. But comfort can become confinement if the culture discourages change.
The Villages was built for reinvention. People arrive as newcomers and quickly adopt new identities: athlete, small business owner, painter, organizer, consultant, mentor. It’s a place where your past matters less than your current curiosity.
Takeaway: Familiarity protects us, but it doesn’t always stretch us. Some communities make it easier to start over.
3. Privacy vs. visibility
Downtown Wheaton is quiet by design. People value their privacy. You nod at neighbors as they pass by. Social life tends to happen behind closed doors or within long-standing circles. That works well for people who already have a built-in network.
The Villages, by contrast, encourages visibility. There’s no shame in showing up to a new activity or starting over in your 50s, 60s, 70s, or beyond. Culture creates expectations. And when those expectations nudge you toward participation, people often rise to meet them.
Takeaway: What we normalize in public shapes what people feel permitted to pursue.
4. Aging alone vs. aging in rhythm
Downtown Wheaton supports aging in place — but often as a solitary process. The systems assume people will manage on their own, or with quiet support from family. That works, until it doesn’t. There’s little redundancy if someone disconnects.
The Villages functions like a small city tuned to the rhythms of aging. From mobility access to social programming, the place is designed to respond as people’s needs change. Aging here is more dynamic, less invisible.
Takeaway: Well-designed communities don’t just make things easier. They help people feel seen.
5. Maintenance vs. anticipation
Downtown Wheaton keeps things running. The sidewalks are shoveled. The post office still works. But the systems aren’t built to evolve with the changing needs of an older adult population. Most infrastructure is reactive.
The Villages is built with aging in mind from the start. It plans ahead. You don’t have to fight for a bench, a spot on the trail, or a group to join. These features aren’t add-ons. They’re defaults.
Takeaway: It’s not about luxury. It’s about planning. Anticipating need beats reacting to crisis.
You Can Create a “Longevity Village” Without Moving
I love both of these communities. One is where I originally thought I’d spend the rest of my days. The other was a surprise that aligned with my personal and professional life — and ultimately opened my eyes to understanding what things could look like as I prepare for later stages of life.
After spending time in both communities, it’s clear that these lessons aren’t confined to a single zip code. The principles that shape meaningful aging can be applied almost anywhere. Things like connection, visibility, and anticipation.
The Villages isn’t unique because of its location. It’s unique because someone thought ahead. It’s a system that anticipates what people might need physically, emotionally, and socially in later stages of life.
That kind of planning can happen anywhere. You don’t need palm trees. You need intention. A walkable town with porch culture. A mid-rise with shared programming. A community center with open hours and flexible space. A street where people feel safe lingering and talking.
None of these are exotic. But they require a shift — from reacting to aging, to preparing for it.
Design That Plans Ahead Is Design That Supports Aging
Downtown Wheaton offers stability and access. The Villages offers structure and stimulation. Both are valid. But neither happened by accident.
The future of aging won’t be decided by location alone. It will be shaped by how well our systems anticipate need, encourage agency, and create opportunities for growth. The most successful communities — whether in Illinois or Florida — will be the ones that stop asking how to preserve the past and start asking how to support what’s next.
A Question Worth Asking
What has your current environment taught you, or failed to teach you, about how you want to grow older and plan for the 3rd and 4th quarters of your 100-year life?
Let me know by leaving a comment.
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 really relate to this piece Bryan as I am on my second stint in the Chicago suburbs (I'm in a neighboring area to Wheaton and I enjoy your area too). I've also lived in Florida (Tampa area) twice. To me there's nothing like Chicago and the Midwest in general in the late Spring/Summer/early Fall when it comes alive full of music and activities. I prefer it to my time in Florida overall, especially Summer, except for a couple of months a year.
As I consider my own future retirement, I don't feel there's one perfect place to be year-round.
I'd love to be able to divide my time between Chicago and another warm area to avoid the bulk of Winter and am always interested in how people handle the safety and security of their "other" home in today's world when they are away.
I imagine you have family on each end? I don't align on both ends that way unfortunately. Would love to see you do a piece on this.
So intriguing to see a perspective from your generation! Love it. I just wrote an article (on Medium though) about a similar topic. Acknowledging your good insights, there can be advantages to living in place rather than in a supported environment. Those advantages include intergenerational relationships that are very important to positive aging, as well as continued responsibility for one's life needs that serve mental and physical wellness as we age. You might take a look at Ken Stern's new book Healthy to 100. Your audience can begin to live right now in a way that will serve their life and health spans. THAT is an important topic! Cheers to you, Ardith