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

July 23, 2026

Buyers

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

Every year, on the third Saturday in July, there is apparently a holiday called National Toss Away the “Could Haves” and “Should Haves” Day.

Is it widely celebrated? Probably not.

But the idea behind it is something most of us can relate to. We all have decisions we look back on and wonder whether we should have done something differently.

Maybe you should have bought that stock before it took off. Maybe you could have kept the classic car you sold years ago. Maybe you should have taken the job, started the business, or made a different choice somewhere along the way.

Real estate creates plenty of “could haves” and “should haves,” too.

Lately, I have heard versions of these two comments more often:

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

“Maybe I should wait until the market gets better.”

Both are understandable. Neither makes it any easier to decide what to do today.

Why Some Sellers Are Choosing to Wait

Across the country, more homeowners have been putting their properties on the market and then deciding to take them back off when they do not receive the price or response they expected.

That is not especially surprising.

For several years, sellers became accustomed to homes selling quickly, multiple offers, buyers waiving contingencies, and properties closing above the asking price.

That was an extraordinary market. It was never going to last forever.

Today, buyers may have more choices. They are taking more time to make decisions, paying closer attention to condition and value, and negotiating more than they did a few years ago.

In Mammoth Lakes and throughout the Eastern Sierra, the market can also vary significantly depending on the property type, price range, location, condition, HOA expenses, rental potential, and even the time of year.

Some properties continue to receive strong interest. Others require more patience, strategic pricing, and a willingness to respond to buyer feedback.

For a seller who remembers the height of the market, that change can be frustrating. It can lead to the thought, “Maybe I should just wait.”

For some homeowners, waiting may be the right choice. But it should be a decision based on their current circumstances and goals, not simply disappointment that today’s market does not look like the market of a few years ago.

Yesterday’s Market and Tomorrow’s Market

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

“Maybe I should wait until the market gets better.”

These thoughts are more closely connected than they may seem.

One looks backward and wishes it were possible to take advantage of yesterday’s market.

The other looks forward and hopes the perfect market will be easy to recognize when it arrives.

The problem is that no one can sell three years ago, and no one knows exactly what the market will look like three years from now.

Interest rates could decline. Inventory could rise. Buyer demand could increase. Economic conditions could change. New regulations, insurance costs, HOA expenses, or local development could also influence value and demand.

There are simply too many variables to predict the future with certainty.

The best decision is usually made by looking at what the market is doing today and deciding whether it supports your personal goals.

A More Normal Market Is Not Necessarily a Bad Market

Today’s market is not automatically a bad market for sellers.

Property values remain strong in many areas, and buyers continue to struggle with affordability. Well-priced and well-presented properties are still selling.

What has changed is the amount of leverage sellers have.

A property may take longer to sell. It may receive fewer showings. A buyer may request repairs, closing-cost assistance, or other concessions. Sellers may need to negotiate rather than simply choose from several offers.

That does not necessarily mean there is something wrong with the market or the property.

It may simply mean we have returned to a more balanced and selective market.

Normal can feel disappointing when it is compared to one of the strongest seller’s markets we have experienced. But extraordinary should not become the standard by which every future market is judged.

Every Market Eventually Becomes a “Should Have”

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

Years later, it is easy to look back and see when someone should have bought, sold, or invested. It is much harder to recognize that moment while you are living through it.

Some sellers who wait will be glad they did. Their circumstances may change, values may improve, or the market may become more favorable for their particular property.

Others may look back and wish they had sold when they had the opportunity.

The truth is, none of us knows which outcome will happen until we are looking at the market in the rearview mirror.

That is why “could haves” and “should haves” are not the best way to make a real estate decision.

A better approach is to look at the current market, understand how properties similar to yours are performing, consider your financial and personal goals, and make a decision based on facts rather than regret or speculation.

If you are deciding whether to sell, wait, or relist a property that did not sell, start with an honest conversation with a knowledgeable local real estate professional.

The goal should not be to perfectly time the market. The goal should be to make the best decision for your situation with the information available today.

National Toss Away the “Could Haves” and “Should Haves” Day may not be a major holiday, but its message is a good one.

Yesterday’s market is gone. Tomorrow’s market is unknown. Today’s market is the one we can actually work with.

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