8 Things Boomers Will Regret Downsizing in 2024

Born between 1946 and 1964, Baby Boomers are currently between the ages of 60 and 78, likely already retired or on the cusp of retirement.

With retirement comes the need — practical, financial, or otherwise — for downsizing. But oftentimes, people end up downsizing either too quickly or too much and later regretting their decision.

If you’re thinking about downsizing, or if you know someone who is, try to take the process slowly. As you get started, here are some of the top things Boomers are likely to regret downsizing going forward.

One of the most common things people downsize in preparation for retirement is their home. While this can often be a good thing as it means lower costs, less maintenance and less hassles maintaining a larger property, it’s easy to regret letting go of your family home too soon.

“Many Boomers regret selling the family home, especially if they feel rushed into the decision,” said Jeff Rose, CFP and founder of GoodFinancialCents.com. “The emotional attachment to a home filled with memories can weigh heavily. Many aren’t prepared for the grief they feel when leaving the only home they’ve known all their life.”

Melanie Musson, a financial expert with Clearsurance.com, added, “There are definitely benefits to downsizing a home and living in a smaller space that’s cheaper and easier to care for. But there are also benefits to having a larger space that Boomers will miss if they downsize. For example, they’ll regret not having room for family gatherings or for friends and family to stay with them.”

It makes sense to get rid of any vehicles that are cluttering your garage, driveway, or backyard. But just because you’re retiring doesn’t mean you should get rid of the spare car. There might be times when you wish you had it.

“If you and your partner are both retired, you might think that it’s the right time to move to one car instead of two,” said Musson. “However, you’ll regret it because there will be times you both want to do your own thing and only having one means of transportation will limit your ability to do what you want.”

Plus, if something happens to your main vehicle and you need convenient transportation, you’ll no longer have it.

Getting rid of a few items is fine — even encouraged if you’re trying to live a stress-free, more organized life. But go about it too quickly or thoroughly and you’re likely to have some regrets.

“While decluttering is liberating, some Boomers regret parting with items that have sentimental value or could have been useful later,” said Rose. “It’s one thing to streamline your life, but another to find you’ve let go of things that were part of your identity or could have been passed down as family heirlooms.”

Whether it’s something from your own childhood or your kids’ childhood, you might regret getting rid of too many of your kids’ toys or belongings.

“Getting rid of clutter can be freeing, but if you have grandkids, you’ll want to make sure they have something to do when they’re at your house,” said Musson. “You don’t want to be the boring grandparents. If you get rid of everything kid-friendly, you’ll regret not having the things your grandchildren love.”

Retirees who give up their current community without truly weighing their options and making sure it’s the right decision for them are likely to have regrets later on.

“For some, downsizing means moving 10 minutes across town; for others, it can mean a cross-country move. Uprooting a community that was built over decades is no easy thing to do,” said Geoffrey Schaefer, CFP and wealth advisor at Intergy Private Wealth.

If you’re moving to be nearer your children or grandchildren, this might be an easy decision — especially if you don’t have a lot that you’re leaving behind. But if you have a thriving community and are happy and settled where you are, letting go can be tough.

Boomers aged 65 and older typically qualify for Medicare. But for those who retire a little earlier and aren’t yet eligible for benefits, it might be tempting to cut costs and go down a healthcare plan. This can be costly and lead to some major regrets.

“Downsizing health insurance to save money could backfire, especially as health concerns grow with age,” said Ian Rodda, CFO at Page One Formula. “Opting for lower premiums now could lead to regret when faced with high medical costs later.”

Anything that leads to the loss of independence is something Boomers — and other retirees — are bound to regret.

Take, for example, someone who owns their own home with a yard and some space between themselves and their neighbors. If they move into a much smaller place or a 55 or older retirement community, they lose some of the privacy and space they once had. This could be a stressful or frustrating experience.

Whether it’s in the interest of saving money or a byproduct of moving somewhere else, Boomers who give up their hobbies or interests tend to hold some regrets, too. The same goes for those who drastically lower their budget for such things and can no longer afford to enjoy them as they once did.

Retirement should be a time of freedom and the ability to pursue those things that matter most to you. If you have the time but can no longer enjoy the lifestyle you want, it can lead to regret, disappointment, or even the feeling of missing out.