If you're thinking about moving, there's probably one question that keeps coming up. Do you sell your home first, or find the next one first and sell after?

Here's where it gets uncomfortable. You find a home you really like, but your current home hasn't sold yet. Do you risk buying it anyway, or sell first and risk having nowhere to move to?

If you're caught between those two choices, that stress makes sense. You're not really deciding which house comes first. You're deciding which kind of uncertainty you're more comfortable carrying, and that's a very different question. There isn't one answer that works for everyone, so rather than tell you to always sell first or always buy first, here's how I walk clients through figuring it out.

What are you actually worried about

Which situation would bother you more? Selling your home while your closing date gets closer and you still haven't found somewhere you want to live. Or buying the next home while your current one is still for sale, with two sets of expenses and possibly two mortgages piling up each week.

Whichever one made you more uncomfortable just reading it tells you something real about how you handle uncertainty, not just about the money.

What selling first really looks like

Once your house sells, you know what you have to work with. Your sale price, your equity, what you can comfortably spend next. You're not guessing, and you're not carrying two properties while you look.

But then comes the real question: what happens if you don't find the right home before yours closes. Could you stay with family, rent for a while, put belongings in storage, and would you still be okay with that if it lasted two or three months instead of two or three weeks? Some people would much rather deal with a temporary rental than carry two homes. For others, especially after 20, 30, or 40 years in one house, the thought of moving twice sounds exhausting. Both reactions tell you something real.

What buying first really looks like

Buying first gives you certainty about where you're going. You find the right home, plan around a real closing date, and ideally move directly from one home into the next. No temporary rental, no storage, no second move.

But it raises a different question: what happens if your current home takes longer to sell than expected. Could you comfortably carry both homes for 30 days? 60? 90? That word comfortably matters, because there's a real difference between being approved to buy first and being comfortable buying first. A lender can tell you something is possible. What matters is how it would feel if the timing doesn't go exactly to plan.

About bridge financing

In simple terms, bridge financing may help you access money for the next purchase during the gap between buying and receiving proceeds from your current home's sale. But the cost and your eligibility depend on your own financial situation and your lender's requirements.

So instead of asking whether you can get bridge financing, ask what it would actually cost if the overlap runs longer than expected. Ask about 30 days, 60 days, and 90 days. You want to understand the smooth-case scenario and the harder one, so you're making this decision with your eyes open.

Your current home matters too

Not every property has the same buyer pool. A typical home in an active neighbourhood carries one kind of risk. A rural property, acreage, an unusual home, or one at a higher price point may simply have fewer buyers looking for it. That doesn't mean anything is wrong with your property, it just means you shouldn't assume it will sell within a set number of days without a realistic look at how it's likely to perform in today's market.

There may be a third option

Buying first and selling first aren't always the only two choices. Sometimes there's room to negotiate a longer closing on your sale, a purchase closing date that lines up more comfortably, or temporary accommodation you'd actually be happy with. Sometimes the right answer is simply to wait, and build the plan around your circumstances instead of a rule of thumb.

Your life matters as much as the numbers

Maybe the upkeep has become too much, or you want to be closer to family, or stairs are getting harder. If you're 68 and you've lived in the same home for 30 years, moving twice feels different than it would have at 35. For some people, stability during the move is worth paying a little more for. For others, carrying two properties for even a short period would be too stressful. Neither is wrong, they're just different priorities.

Where I'd start

Before listing your home or making an offer, it helps to know three things: what your current home could realistically sell for today, what your financing options actually look like, and what Plan B looks like if the timing isn't perfect. Perfect timing sounds wonderful, but the better goal is knowing you're still okay if something takes a little longer than expected.

If you're standing in the middle of this decision, I'm happy to talk it through, no obligation, and no need to have the answer before we talk.