The Myth of Always Winning in Real Estate

Many of us have been taught that “you can’t lose money in real estate.” Really? As many of you know, Janice and I just sold our home as part of our downsizing journey — and even though we followed the so-called golden rule, we did, in fact, lose money.

Was it due to a poor buying decision or a misstep in the sales process? I don’t believe so. We didn’t overpay at the time nor did we undersell — but timing is everything. In hindsight, it seems we bought at the peak of the market. Unless you have a crystal ball or plan to hold on to your property for decades, real estate isn’t the guaranteed win it’s made out to be.

According to the latest Standard & Poor’s CoreLogic Case-Shiller Home Price Index, Metro Detroit housing prices have only just returned to their 2007 levels — still about 18% below the regional peak of 2005–2006. While sales are bouncing back, that doesn’t erase the fact that many homeowners, ourselves included, didn’t come out ahead.

Is Homeownership Really the Best Investment?

We’ve all heard the saying: your home is your biggest and best investment. But if your “investment” delivers a negative return, is it really an investment — or just a costly illusion?

We were also sold the idea that buying a home is part of the American Dream. And yet, that dream doesn’t always come with a happy ending. It feels a bit like “The Wizard of Oz” — where everything seems magical until you pull back the curtain. So who’s really behind the messaging? Mortgage companies? Home builders? The government, eager to collect more property tax from homeowners than renters?

Rethinking the Narrative

There are a few other common beliefs we might want to challenge:

• “Buy the biggest house you can — you’ll grow into it.”

• “The bigger the mortgage, the bigger the tax deduction.”

Sound familiar? My advice: be like Dorothy. Pull back the curtain. Question the motives. Owning a home isn’t inherently bad — but going in with eyes wide open and not blindfolded by myths may be your smartest financial move.

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