Over the weekend, I listened to a radio discussion about people who repeatedly run for political office but never win. They were described as “perennial” or “serial” candidates.

We have a local example of someone who has run for mayor, regional chair several times, and as a Progressive Conservative candidate in a provincial election, without success. At some point, you might think it would be time to move on. Then again, with another election approaching, perhaps it is time to try once more.

The discussion made me think about what causes someone to pursue a major life change that requires so much energy, emotion and determination. Homeowners can face a similar question, particularly those who bought during the real estate boom of 2020 to 2022 and are now considering a move.

The market during those years looked nothing like it does today. Homes were selling almost overnight, bidding wars were common, and many properties sold for $200,000 or more above the asking price.

One of my clearest memories from that period was standing in a lineup of agents and buyers, waiting for a 15-minute appointment to view a home priced at $2 million. That was simply how the market worked at the time.

The rise in detached-home prices was dramatic. In Oshawa, the average price increased from approximately $665,000 in July 2020 to $1,218,000 in February 2022. In Whitby, the average rose from $828,000 to $1,548,000. In Clarington, it climbed from $709,000 to $1,257,000.

Current average detached-home prices are approximately $788,000 in Oshawa, $1,070,000 in Whitby and $872,000 in Clarington.

For someone who bought near the peak and now needs to sell, the decline can feel devastating. The difficult question becomes: when do you accept the loss, pull the plug and move on?

The answer depends largely on what type of buyer you were and what happened before the purchase.

A move-up buyer who sold one property to purchase a larger home may not be in as difficult a position as it first appears. I once represented a seller whose home was purchased by someone buying near the peak. That buyer had also sold a townhome in the same market.

Today, the home they purchased is worth less. However, the townhome they sold would also be worth considerably less if they had kept it. They bought high, but they also sold high. The decline in value affected both properties, which softened the overall impact.

A downsizing buyer may be in a similar position. If someone sold a larger home and purchased a smaller one during the peak, both properties may have since declined in value. The numbers can look painful when viewed separately, but the homeowner may still be in roughly the same financial position relative to the market.

The most difficult situation usually involves the first-time buyer. That buyer did not have another property to sell at an inflated price. Their down payment and mortgage went directly into a home purchased near the top of the market.

If the home is now worth less than the outstanding mortgage, the owner is considered “underwater.” Most lenders will allow the homeowner to remain in the property as long as the mortgage payments continue to be made. In that case, it becomes a waiting game. The homeowner stays put, continues paying down the mortgage and waits for values to recover.

Of course, staying in the home is not always possible. A homeowner may need to relocate for work, separate from a partner, move closer to family or sell because of financial pressure.

A seller who is leaving the housing market entirely, perhaps to move out of the area or become a renter, may also be forced to accept less equity than expected. Unlike a move-up or downsizing buyer, they are not purchasing another home at a reduced price, so the loss is more direct.

When prices decline, the best financial strategy is often to stay in the home, continue enjoying it and give the market time to recover.

Over the past four decades, I have worked through four major real estate downturns. In each cycle, the buyers most affected were those who purchased within roughly a year of the market peak.

People who bought earlier, while prices were rising, usually had more protection. Their homes may have declined in value, but often not below what they originally paid. In previous cycles, values eventually recovered, although the length of time varied.

We are now more than four years beyond the February 2022 peak. If history follows a familiar pattern, the market should eventually begin moving upward again.

However, there is one important difference this time. Builders have sharply reduced new construction, and Ontario housing starts in 2026 are expected to be among the lowest seen in approximately 20 years.

That matters because housing construction works on a long pipeline. The homes not started today will not be available three, four or five years from now.

For the moment, the market may appear to have enough inventory because demand is weak and buyers remain cautious. That can change quickly when interest rates become more manageable, confidence returns and more people decide to move.

If demand strengthens and the supply of newly completed homes is not there to meet it, buyers will be forced to compete for the homes already available. A growing population, fewer new homes and limited construction capacity create a familiar result: rising competition, rising prices and another housing shortage.

It is basic economics. The housing crisis of the future may not begin when buyers return. It may already be beginning today, with the homes builders have decided not to build.

So, when is it time to move on?

For a perennial political candidate, that is a personal decision. For a homeowner who purchased near the top of the market, moving on may be less important than understanding whether moving right now makes financial sense.

Sometimes persistence is denial. Sometimes it is simply refusing to sell at the worst possible moment with fingers crossed for a quick recovery.

If you are a homeowner and considering if now is the right time to move, I can be reached at lindsay@buyselllove.ca or 905-743-5555