Thinking About Selling Your Home? It Might Be Time to Toss Away the “Could Haves” and “Should Haves.”

Every year, on the third Saturday of July, millions of people celebrate National Toss Away the “Could Haves” and “Should Haves” Day.

OK… maybe not millions. But somebody probably does!

While it’s not exactly the kind of holiday most people mark on their calendars, it’s built around an idea that’s surprisingly relatable. We all have moments we wish we could do over.

Maybe you could have invested in a company before its stock took off. Maybe you should have kept that classic car instead of selling it years ago. Maybe you could have taken that job, started that business, or simply made a different decision somewhere along the way.

Real estate has no shortage of “could haves” and “should haves,” either.

In fact, one that’s been floating around quite a bit lately sounds something like this:

“Maybe I should have sold my house a few years ago.”

“Maybe I’ll just wait until the market gets better…”

If you’ve been paying attention to the housing market lately, you may have noticed that some homeowners are putting their houses up for sale… and then deciding to take them back off the market.

According to recent data, delistings have been on the rise as more sellers decide they’d rather wait than accept a market that isn’t quite living up to their expectations. In fact, they’re delisting at the highest rate since 2020, right around the time the pandemic began.

When you think about it, it’s not hard to understand why.

For several years, many sellers got used to homes selling almost immediately, multiple offers arriving within days, buyers waiving contingencies, and offers coming in above asking price.

But, as real estate markets tend to do, they’ve changed in many areas.

Depending on where you live, and the price range your home is in, buyers may have more choices than they’ve had in years. They may take longer to make a decision. They’re more likely to ask for inspections, repairs, seller concessions, or simply negotiate harder than they would have a few years ago.

For some homeowners, that shift is frustrating enough to make them think…

“Maybe I’ll just wait until the market gets better.”

And for some people, that may absolutely be the right decision.

Two Thoughts That Are Closer Than They Appear

What’s interesting is that the two thoughts we’ve been talking about are actually pretty close cousins.

“Maybe I should have sold my house a few years ago.”

“Maybe I’ll just wait until the market gets better.”

One is based on wishing you could go back and capitalize on yesterday’s market.

The other is based on hoping you’ll recognize the right time to capitalize on tomorrow’s.

They’re both completely understandable. In fact, they’re probably thoughts just about everyone has had at one point or another—not just in real estate, but in life.

The catch is that neither one is particularly helpful when you’re trying to decide what to do today.

After all, you can’t sell your house three years ago.

And no one—not even the smartest economists—knows exactly what the housing market is going to look like three years from now. Or any other number of years for that matter. You can only make decisions based on what the market is currently doing.

The Problem With Using Extraordinary as Your Baseline

It’s also worth remembering that today’s market isn’t necessarily a bad market for sellers.

In many parts of the country, home prices are still historically strong. In fact, if you ask many buyers how they feel about today’s market, there’s a good chance they’ll tell you homes are still too expensive and affordability remains one of their biggest challenges.

What’s changed isn’t necessarily that sellers have lost all of their leverage.

It’s that many of them have lost the extraordinary leverage they enjoyed just a few years ago.

But now your home may take a little longer to sell. You might not have quite as many showings. Your buyer may ask for repairs or seller concessions that would have been laughed off during the frenzy of the pandemic market.

None of those things necessarily mean it’s a bad time to sell. They may simply mean the market has become a little more… normal.

And normal can feel disappointing when you’re comparing it to one of the strongest seller’s markets in modern history.

Every Market Creates a Few “Should Haves”

One of the interesting things about real estate is that every market eventually becomes the one somebody wishes they’d taken advantage of.

Looking back, it’s easy to find a market where you wish you had bought, sold, or invested. The challenge, of course, is that nobody knows which market people will be saying that about until years later.

Will some homeowners who decide to wait ultimately be glad they did? Absolutely. Every seller’s situation is different, and for some, waiting may prove to be exactly the right decision.

But chances are, this market will also become one that at least some homeowners eventually look back on and say, “I probably should have sold then.”

The only problem is that none of us knows which market that will be until we’re looking at it in the rearview mirror.

That’s why “could haves” and “should haves” usually aren’t the best guide when making real estate decisions. They only show up after the fact.

If you’re debating whether to sell now, wait a while, or even relist a home you recently took off the market, one of the smartest things you can do is have a conversation with a knowledgeable real estate agent. They can help you evaluate your local market, your personal situation, and your long-term goals so your decision is based on today’s realities—not yesterday’s regrets or tomorrow’s unknowns.

And if nothing else, perhaps National Toss Away the “Could Haves” and “Should Haves” Day is a good reminder that yesterday’s market is gone, tomorrow’s market hasn’t arrived, and today’s market is the only one any of us actually gets to make decisions in.