Don’t Let Regret (or Fear of it) Run the Show

Overthinking rarely leads to better outcomes—just longer delays

This would be a good time to remind everyone I’m not a CPA, a financial professional, or an attorney. I’m a real estate broker. This isn’t financial or legal advice. Talk to a professional before making any big decisions.

Back when I got into real estate, there was a broker who used to say, “Any deal is a good deal if you give it enough time.”

Half joke, half truth. I watched him put people in deals that eventually worked out—but took a lot longer than he probably sold them as.

Even if you overpay around here, odds are you’ll be “proven right” if you wait long enough. I’ve seen people make good money off properties I thought were overpriced 20 years ago. All of them are worth more now.

A smart aleck might say my only mistake was doing due diligence.

But here’s the thing: annual return matters more than gross return.

Sure, land held for 20 years might look good on paper. But what could that money have been doing for you in the meantime?

By buying and selling when prices were good relative to the market, my clients often made better returns than if they had just held.

That doesn’t mean you should sell just because. But it also doesn’t mean you should hold forever out of fear you’ll regret it.

Here are a few good reasons to sell:

• You need the money. (I’ve got kids in college—enough said.)
• You’ve got a better opportunity. Favorable tax treatment might make it smart to sell one and buy another.
• Estate planning. Sometimes selling is simpler and keeps peace in the family.
• You want more land and less traffic. Sell in the growth area, move a little further out, and repeat. Plenty of people have built wealth this way.

The point is: no matter what you do, you might feel like you made the wrong call later. That’s normal. But it’s also not helpful.

Do the best you can with the info you have, for the right reasons at the time. Then look forward—not back.

No pressure. But if you’re ready to talk it through, you know where to find me.

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