If there’s one thing we hear from downsizing clients more than anything else, it’s this: ‘I wish I’d started sooner. It’s not “I wish I’d waited for a better market.” Not “I wish I’d gotten a higher price.” It’s always about time.
And yet, when we meet with people who are thinking about downsizing, the first question is almost always the same: “Should I wait for the market to improve?”
The honest answer? Probably not. And here’s why.
The Market You’re Waiting For May Not Be Coming
We understand the instinct. You’ve lived in your home for 20, 30, maybe 40 years. You’ve watched the market go up and down and up again. It feels like if you just wait a little longer, you’ll sell at the peak and buy at the bottom.
The problem is that nobody can time the market consistently, and that includes real estate agents. We’ve been doing this for a long time and we still can’t predict what the market will do six months from now. Nobody can. What we can tell you is what the data says right now, what comparable homes are selling for in your neighbourhood, and what your realistic options look like today.
Remember: if you’re both selling and buying in the same market, the conditions largely offset each other. If the market goes up 10%, you’ll sell for more but you’ll also pay more for your next home. If it goes down, you’ll sell for less but you’ll also buy for less. The offset isn’t perfect for downsizers (if you’re selling a higher-priced home and buying a lower-priced one, a percentage drop costs you more in dollars on the sell side than you save on the buy side), but the impact is usually much smaller than people assume. It’s rarely the dramatic windfall or disaster that keeps people frozen in place for years.
So waiting for the “right” market often means waiting for something that won’t move the needle nearly as much as you think it will. If it comes at all.
The Real Cost of Waiting
When our downsizing clients say they wish they’d started sooner, they’re not usually talking about money. They’re talking about time.
The reality is that downsizing takes a lot longer than most people expect. There’s the emotional process of deciding to move in the first place, which for many people takes months or even years. Then there’s the practical work: decluttering a home you’ve lived in for decades, making repairs, getting the house ready for sale, figuring out where you want to move, understanding condo fees and maintenance and all the things that come with a different kind of home.
Most of our downsizing clients need anywhere from six months to a year to get from “we’re thinking about it” to “we’re ready to list.” And that’s after they’ve made the decision. The ones who started early, who gave themselves the luxury of time, consistently have a better experience than the ones who waited until they had to move. Urgency is never your friend in real estate.
Meanwhile, every month you wait is another month of maintaining a home that’s probably too big for your needs. Property taxes, heating bills, repairs on a house that’s aging along with you. Those costs add up, and they’re easy to ignore when you’re focused on the hypothetical sale price.
Related: The Art of Downsizing Your Home to Save Money
Starting the Process Doesn’t Mean Listing Tomorrow
One of the biggest misconceptions we see is that “starting” means putting a For Sale sign on the lawn next week. It doesn’t. Starting means having a conversation. It means getting a sense of what your home is worth today, understanding your options, and beginning to think about what you want your next chapter to look like.
For a lot of our retired downsizer clients, that first conversation happens a full year or more before they actually list. And that’s perfectly fine. In fact, it’s ideal. It gives you time to declutter at a pace that doesn’t feel overwhelming. It gives you time to make any repairs or updates that will actually impact your sale price (and skip the ones that won’t). It gives you time to explore neighbourhoods and housing options for your next home without the pressure of a closing date hanging over your head.
Related: Downsizing Your Personal Belongings: A Guide to Making Tough Choices
Related: Complete Downsizing Guide for 65+ Homeowners
The Buy-Sell Timing Question
The other timing question that keeps downsizers up at night: “Should I buy first or sell first?” The honest answer is that it depends on your financial situation, your tolerance for risk, and what the market is doing right now. There’s no universal right answer.
What we can tell you is that having a plan for both scenarios, and a backup plan if neither goes perfectly, is far more valuable than trying to time everything down to the day. This is where working with an experienced agent (or team) makes a real difference. We’ve helped enough downsizers navigate the buy-sell juggle that we know where the pressure points are and how to manage them.
Related: Should You Buy or Sell First?
The BREL Bottom Line
The number one regret we hear from downsizers isn’t about price. It’s not about the market. It’s “I wish I’d started sooner.”
Not listed sooner. Started sooner. Given themselves more time to sort through a lifetime of belongings, more time to explore their options, more time to make decisions without pressure.
If you’ve been thinking about downsizing but keep telling yourself you’ll do it when the market is right, consider this: the best time to start the conversation is almost always now. Not because the market is perfect (it never is), but because time is the one thing you can’t get back, and having more of it makes every part of this process better.
Related: The No-Nonsense Guide to Downsizing From a House to a Condo