05/04/2025
WORTH A READ:
8 housing regrets retirees admit after downsizing too soon
Bernadette Donovan
Let’s face it: retirement can be a roller coaster—exciting one minute, daunting the next.
And for many of us, one of the biggest leaps in this new chapter is deciding whether (and when) to downsize our homes.
In my own retirement journey, I’ve witnessed friends, former colleagues, and even a few of my old high school teaching buddies grapple with the decision to move into a smaller space.
Some did it flawlessly, while others found themselves saying, “If only I’d thought of that sooner!”
I’m not suggesting downsizing is always a mistake—far from it. For many retirees, it’s a strategic and liberating move.
But if there’s one thing I’ve learned in my years as both an educator and a retiree, it’s that hindsight is often 20/20. With that in mind, let’s dive into eight housing regrets that retirees commonly admit after downsizing too soon.
My hope is that by exploring these pitfalls, we can help you avoid them—or at least prepare you for what lies ahead.
1. Underestimating future space needs
One of the first regrets I hear from folks who jump into downsizing is that they underestimated just how much space they’d still want, even in retirement.
It’s easy to think you won’t need a home office anymore, or a dedicated craft room, or a spacious kitchen.
But, as I discovered after retiring, new hobbies (like volunteering in community literacy programs and hosting weekly book club meetings) can require more room than we expect.
Plus, if you have grandchildren like I do—mine absolutely love their sleepovers—you might want that extra bedroom. Or perhaps you’ll need space for your adult children who visit more often than you think.
Winston Churchill once said, “Let our advance worrying become advance thinking and planning.”
That rings true here: consider your hobbies, family gatherings, and potential future needs, rather than rushing to clear out all that square footage.
2. Letting go of sentimental items too quickly
Downsizing often comes with a lot of decluttering, and I’m a big believer in passing on items we no longer use.
But there’s a fine line between minimizing and feeling like you’ve lost part of your personal history. Over the years, I’ve seen retirees donate or toss treasures—photo albums, heirloom furniture, or that old rocking chair their mother once used—only to regret it later.
The tricky part is figuring out what to keep. My rule of thumb: if it represents a cherished memory or part of your family’s story, think twice before letting it go.
You don’t want to wake up one morning in your new, smaller home and realize the one item that brought a smile to your face is gone.
Consider digitalizing old photos or passing keepsakes to family members who can care for them until you have more space or decide what you truly want to hold onto.
3. Overlooking the importance of community and social ties
One piece of advice I gave my high school students—and now find myself repeating to retired friends—is that we’re wired for connection.
Retirees often regret downsizing into a charming little place that’s far from their lifelong friends, church community, or volunteer activities. It’s one thing to have a cozy new house, and another to feel isolated and disconnected from your social circle.
Brené Brown, a well-known researcher on vulnerability and connection, has famously said, “Connection is why we’re here.” After decades teaching about literature’s exploration of the human condition, I firmly believe she’s right.
Think long and hard about whether your smaller home will leave you cut off from the people and places that energize you.
Are you willing to drive longer distances to attend your grandchild’s recital or a weekly book club? If the answer is no, location might matter more than size.
4. Miscalculating the financial reality
Downsizing, in theory, sounds like an easy way to free up cash and reduce expenses.
Less property tax, fewer utility bills, reduced maintenance—it’s a perfect equation, right? Not always.
Many retirees admit they were blindsided by the costs of moving, renovating a new space to fit their needs, or even dealing with higher homeowner association fees in certain communities.
I mentioned in a previous post on DMNews that financial surprises can derail an otherwise fulfilling retirement plan. I’ve seen folks get so caught up in the promise of a simpler life that they don’t run the numbers carefully enough.
The lesson here? Look beyond the sticker price. Do a thorough budget that accounts for every likely (and some unlikely) expense. Talk to friends or family who’ve already downsized.
And if you can, consult a trusted financial advisor to be sure you’re prepared.
5. Failing to consider future mobility issues
If there’s one thing I learned from my years teaching teenagers, it’s that we all think we’ll remain forever young—until suddenly, we realize we’re not.
A number of retirees regret moving into smaller spaces that aren’t mobility-friendly, such as condos with stairs at every turn or bathroom layouts too narrow for walkers or wheelchairs should they become necessary.
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At first, you might think, “I’m healthy now, so I’ll just manage.” But as we age, certain design features can become essential: grab bars in the shower, single-story living, wider doorways, ramps, and so on.
Even if these accommodations feel premature, planning ahead can save you from yet another disruptive move if health challenges arise.
Bill Gates once said, “We always overestimate the change that will occur in the next two years and underestimate the change that will occur in the next ten.”
That applies not just to technology, but to our own aging process, too.
6. Not factoring in space for hobbies or passions
When I first retired, I imagined endless days volunteering at local literacy programs, attending yoga classes, and trying new healthy recipes.
I didn’t consider how much space some of those activities might require. A friend of mine, for instance, discovered she couldn’t properly do her watercolor painting in her cramped apartment.
Another realized he missed the workshop in his old garage for woodworking.
Whether it’s gardening, painting, yoga, or a home-based side hustle, retirees often lament that they said goodbye to the one place that let them nurture their passions.
If you’re moving somewhere with shared community spaces—a common feature of 55+ communities—investigate how accessible they really are.
Will you be able to reserve a craft room or rec center when you need it? Make sure your new home (or the surrounding area) can accommodate the activities that make you feel alive.
7. Neglecting to plan for visiting family or caregivers
Many of us baby boomers dream of hosting holiday gatherings, or at least having a comfortable space when family visits.
I’ve heard countless stories of retirees who jumped into a two-bedroom downsized home, only to realize it barely fits them, let alone grown children, grandchildren, or a caretaker who might need to stay overnight.
Even if you don’t anticipate family moving in with you, life has a way of surprising us.
Grandkids might need a place to crash for summer break. A caregiver might need a bedroom if you or your spouse face health issues down the road.
The regret sets in when retirees find themselves saying, “We never thought we’d have someone living with us again.” Being open to these possibilities ensures you’re not caught off guard.
8. Moving away before exploring other options
I’ve saved this regret for last because it often emerges when folks look back on the whole experience and realize they could have tried something else first.
Could they have rented out part of their home for extra income? Taken in a housemate or relative? Could they have done a smaller renovation to make the house more retirement-friendly?
Sometimes, downsizing is the best (or only) move. But if you haven’t explored other possibilities thoroughly—ranging from partial renovations to short-term rentals in a retirement community—you might find yourself with seller’s remorse.
Before you box up everything, do a little detective work on all the alternatives.
Is there a program in your community that supports aging-in-place upgrades? Is there a friend or neighbor looking for a living arrangement that could help you both?
Approach this step as you would a major purchase: get your facts straight before signing on the dotted line.
Finally but perhaps most importantly, give yourself grace. Downsizing doesn’t have to be all-or-nothing, and it doesn’t have to happen at breakneck speed.
Even if you’ve made a misstep, remember that we’re all works in progress—especially in retirement. As Albert Einstein said, “Life is like riding a bicycle. To keep your balance, you must keep moving.”
Some of us will decide that a smaller home is exactly what we need, and we’ll have no regrets. Others might hold onto that beloved family home a little longer.
Regardless, the goal is to be intentional. Ask yourself: How do I want to live out these next decades, and what kind of space will truly serve that vision?
Conclusion
Downsizing isn’t just a financial or logistical decision; it’s a deeply personal one that touches on everything from our memories to our future aspirations.
We each have our own unique journey, and there’s no one-size-fits-all answer.
My hope is that by hearing these eight common regrets, you’ll be able to approach downsizing (if you choose it) with a clearer sense of what to watch out for.
