A friend of mine recently told me, with a grin wider than a lottery winner’s, that he’d finally retired. He’s 77. After many years past the “official” retirement age, he’s finally done with work.
That conversation got me thinking about what retirement looks like to me. Spoiler alert: the answer isn’t simple. Retirement looks different depending on who you ask, and in some cases, when you’re asking.
Retirement Isn’t What It Used to Be
Not that long ago, retirement followed a pretty standard script: you put in 40 years at the company, get your gold watch, and spend your remaining days perfecting the art of lawn care. That image might have worked for my grandfather’s generation, and even my dad’s, but for most of us today, the picture has changed. More people are redefining retirement to better fit their lifestyle, their quality of life, and their goals.
People are healthier, living longer, and in many cases, working longer. Some because they want to. Some because they have to. Either way, the idea of retiring at 65, buying an RV, and disappearing into the sunset doesn’t quite capture the reality anymore.
What Retirement Looks Like (for Me)
When I think what retirement looks like to me, I know it’s definitely not about doing nothing. I’d go stir-crazy within a week. Retirement is about no longer working for someone else. It’s about having the freedom to choose. And while I may sometimes have a bit of a tongue-in-cheek view of my own retirement, it doesn’t mean I’m not open to actually having a retirement of my dreams.
That might look like writing when inspiration strikes. Tinkering with online projects. Traveling to new places. Or enjoying a local brew on a Tuesday afternoon without the guilt that I should be doing something more “productive.”
It’s not about stepping off the treadmill. It’s about finally choosing the treadmill I actually want to run on.
What Retirement Absolutely Does Not Look Like
For me, retirement isn’t about stopping my life and settling into an easy chair, watching the world go by. I saw what that looked like with my own parents. They went from being Florida snowbirds for three glorious months each year, walking the beaches, soaking up the sun, and golfing almost every day; to spending Montreal winters barricaded in different corners of the house. One would be tackling crosswords while the other read the newspaper, both trying to ignore the howling blizzard outside. That is definitely not for me.
I know some folks imagine retirement as endless hours of television, working through reruns of Matlock and Murder She Wrote on Netflix. And hey, no judgment if that’s your jam. But for me, that sounds less like freedom and more like slowly losing track of my sanity until I have to ask, “Wait, is it Thursday or dinner time?” If I need a calendar just to remember which show I binge-watched last night, something has gone wrong. Definitely not what retirement looks like to me!
I Shall Not Putter!
Then there’s the stereotype of the hyper-relaxed retiree who putters around the house for decades, occasionally rearranging the garage or polishing the toaster for lack of anything better to do. I’ve never been a great putterer. I like projects with momentum. If you see me endlessly reorganizing nuts and bolts into little jars, it means I’ve officially run out of purpose. Time to set me free on an iceberg. And I’m determined not to let that happen.
Another version I’ve seen is the “geographic freeze.” That’s when people stop exploring, stop traveling, and stop trying new things. They find their favorite chair, their favorite coffee shop, and their favorite news channel, and then repeat those same three comforts until they forget there’s a bigger world out there. To me, that isn’t retirement, it’s retreat. And it’s the opposite of how I want to spend my later years.
So, when I picture what retirement doesn’t look like, I see a life that’s shrunk down too small. A life that’s closed off instead of opening up. Redefining retirement, for me, should be about expanding horizons, not narrowing them. It’s about staying curious, adventurous, and maybe even a little reckless. Because the last thing I want is to wake up one day and realize that instead of living retirement, I’ve just been killing time.
In other words, retirement won’t be about winding down. It will be about winding up in new directions.
The Spectrum of Retirement
The truth is, retirement exists on a spectrum. On one end are those who quit work entirely and never look back. On the other are people who never plan to stop working at all. Most of us land somewhere in between, balancing rest, purpose, and the occasional guilty pleasure.
Some keep a hand in the workforce because they enjoy the social connection. Others dive into volunteering or passion projects. And plenty of folks use the freedom to chase adventure, whether that means traveling the world or finally checking off that dusty bucket list.
*Aside note: One of my bucket list items for the longest time was to open up a little palapa beach bar. But as I’ve gotten older, I realize I don’t want the responsibility of managing staff, ordering products, doing inventory, and all the other headaches of owning a business. No, I’ve refined it down to maybe working a couple of hours at a beach bar. And if that isn’t doable, I’ll sit on the other side of the bar, sampling the product, telling lies and shooting the breeze with tourists. Hey, I’m nothing if not flexible!
My Next Adventure: Retirement Abroad
For me, adventure will be a huge part of retirement. Not just vacations, but real experiences. The plan is to live part-time in Belize and part-time in Canada. Sunshine, sand, Belikin Beer and Mayan jungle for the winter months, temperate rainforests, Provincial parks and family visits for the rest of the year.
We’re also looking forward to visiting our vast network of International students. That’ll have us visiting multiple continents, and maybe saving a ton on accommodations!
Of course, this comes with its own challenges. Empty nesting is fast approaching, and that means redefining home life, too. But that’s the fun of it. Retirement isn’t about stopping. It’s about reshaping. Yeah, fun…we’ll call it that…
How Do You Define Retirement?
When I think back to that conversation with my buddy, the one who retired at 77 with a grin that could light up a room, I realize he wasn’t just telling me he had quit working. He was announcing that he’d stepped into a new chapter on his own terms. It took him a long time to get there, but when he finally did, it was with a sense of pride and relief.
And maybe that’s the heart of it. Retirement isn’t about fitting into someone else’s idea of what life after work should look like. It’s not about locking ourselves away from the world, doing crosswords until the ink runs out, or waiting patiently for time to pass. It’s about choosing what matters to us, right now, in this season of life.
For some, that choice might mean slowing down and savoring the quiet. For others, it might mean chasing adventure or staying engaged in the work they love. Or maybe it is crosswords and Judge Judy! But for me, it’s about shaping a life filled with curiosity, travel, and a fair share of guilty-pleasure pub visits.
At the end of the day, retirement is what we choose to make it. The only wrong path is the one where we give up on living before life has finished with us.
Overseas by Design; Define Your Own Retirement
If you’ve been thinking about what retirement looks like for you, and maybe realizing it doesn’t fit the old script, that’s exactly why I wrote my book, Overseas by Design: The Savvy Retiree’s Roadmap to Living Abroad. It’s for people who want more than just sitting still. It’s for those who want to explore new options, stretch their retirement dollars further, and build a life that feels exciting, not restrictive.
Inside, you’ll find practical tools to help you compare destinations, understand visa and residency options, budget realistically, and even plan for healthcare overseas. But it’s not just a guidebook. It’s also a framework to help you re-imagine retirement on your terms, with the freedom to design a lifestyle that balances adventure, security, and affordability.
If the thought of redefining retirement excites you, I’d love for you to check it out. Overseas by Design is available on Amazon in both paperback and Kindle. Just click the link above.
Whether you’re just beginning to dream about retirement or you’re ready to start planning your next chapter, this book can help you move from “what if” to “why not?”
Freedom 85!!
God please, NO!!