Every year, on the third Saturday of July, someone—somewhere—celebrates National Toss Away the “Could Haves” and “Should Haves” Day.

It may not be a holiday you’ve marked on your calendar, but the idea behind it is something nearly everyone understands.

We all have decisions we revisit.

Maybe you could have invested sooner, kept the classic car, accepted a different opportunity or taken the trip you kept postponing.

Real estate creates its own collection of “could haves” and “should haves,” especially when the market changes:

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

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

Both thoughts are understandable. Neither one, however, tells you what makes sense for your life today.

When Today’s Market Doesn’t Match Yesterday’s Expectations

Some homeowners are entering the market expecting the experience their neighbors had a few years ago: immediate showings, multiple offers, waived contingencies and buyers competing well above the asking price.

But markets change.

Today’s buyers may have more homes to consider. They may take longer to decide, negotiate more carefully or ask for inspections, repairs and closing-cost assistance.

When a home doesn’t sell as quickly—or as effortlessly—as expected, it can be tempting to take it off the market and wait.

For some homeowners, waiting may be the right choice.

But waiting should be a deliberate decision based on your circumstances, not an emotional reaction to a market that no longer resembles an extraordinary moment in history.

Yesterday’s Regret and Tomorrow’s Hope

These two thoughts are more closely related than they first appear:

“I should have sold a few years ago.”

“I’ll wait until the market improves.”

The first looks backward and wishes for another opportunity.

The second looks forward and hopes the ideal opportunity will be obvious when it arrives.

The problem is that you cannot sell your home three years ago—and no one can promise what the market will look like three years from now.

You can only evaluate the market you have, the life you want and the options available to you now.

A More Normal Market Isn’t Necessarily a Bad Market

Today’s market may feel disappointing when compared with one of the strongest seller’s markets in recent history.

That doesn’t automatically make it a bad time to sell.

Your home may take longer to attract the right buyer. You may receive fewer showings. You may need to prepare the property more carefully, price it more precisely or negotiate terms that sellers could dismiss during the frenzy.

Those realities do not necessarily mean you have lost your opportunity.

They mean strategy matters again.

The right question isn’t:

“Can I get what my neighbor received at the height of the market?”

It’s:

“What can this home realistically help me accomplish now?”

Your Home Is Only One Part of the Decision

For retirees and right-sizers, selling is rarely just about maximizing a number.

It may be about reducing maintenance, eliminating stairs, moving closer to family, freeing up equity, simplifying expenses or choosing a home that better supports the way you want to live.

Waiting for a potentially better market has a cost, too.

It may mean another year of upkeep, taxes, insurance, repairs or living in a home that no longer fits. It may delay travel, financial flexibility or the next chapter you are already beginning to imagine.

That does not mean you should sell before you are ready.

It means the decision deserves a broader calculation than price alone.

Every Market Eventually Becomes Someone’s “Should Have”

Looking backward makes real estate decisions appear obvious.

There will always be a year when someone wishes they had bought, sold or invested. The trouble is that we rarely recognize those moments with certainty while we are living through them.

Some homeowners who wait will be glad they did.

Others may eventually look back at today and think, “I probably should have made the move then.”

None of us gets to know that answer in advance.

What we can do is replace speculation with clarity.

If you are deciding whether to stay, adapt your current home, sell, right-size or relist a property you previously took off the market, begin with a thoughtful evaluation of three things:

• What your home could realistically sell for today
• What waiting is likely to cost—financially and personally
• What you want your life to look like next

You do not need to be pressured into selling. You also do not need to remain stuck because yesterday’s opportunity has passed or tomorrow’s outcome is uncertain.

Yesterday’s market is gone. Tomorrow’s market has not arrived.

Today is where you still have choices.

If you would like help understanding those choices, I invite you to begin with Life’s Next Move™—a private, pressure-free conversation about your home, your options and the life you want next.

Natasha Burnett
GoldPhire® | Luxury. Lifestyle. Legacy.
Helping retirees and right-sizers make confident moves in Jasper and the North Georgia mountains.