Buying a home in Portland’s competitive real estate market can feel a lot like stepping up to the plate in the bottom of the ninth inning.

As far as I know, there’s only one guaranteed way for a baseball player to make it safely home.

Hit the ball out of the park.

Lately, helping buyers purchase a home in Portland has felt remarkably similar.

Over the past several months, I’ve watched an unusual number of transactions fall apart for every reason imaginable. I’ve seen bidding wars spiral out of control, homes intentionally priced below market value to attract multiple offers, buyers competing against cash offers, and sellers making split-second decisions that leave hopeful buyers heartbroken.

Who needs television?

This spring market has felt more like a soap opera.

One of my recent clients reminded me why buying a home isn’t just about strategy.

It’s also about mindset.

The very first day we started touring homes, she found it.

Her dream house.

It checked every box on her wish list.

My job seemed simple.

Help her get it.

Before advising any buyer, I study comparable sales to understand what a home is truly worth. In this case, I believed the seller had intentionally priced the home below market value to create competition, and I had a good idea where the final sales price might land.

She was prepared to offer more than $100,000 above asking price.

After the offer deadline, every buyer was invited to improve their offer.

That’s when I had to give advice that surprised her.

“I can’t honestly recommend paying more.”

Nothing supported the value.

Later, the listing agent called.

The bidding had become extraordinary.

One buyer had written an offer so far above market value that no one else realistically had a chance.

She was crushed.

I understood completely.

When you’ve already imagined your future in a home, letting go is incredibly difficult.

But I also told her something I’ve seen proven over and over during my career.

At that moment, those words probably didn’t ease the disappointment.

A few weeks later another home came on the market in the same neighborhood.

She loved this one too.

We submitted another strong offer.

Another offer deadline.

Another disappointing phone call.

“I’m so sorry,” the listing agent said. “The seller accepted an exceptional offer with a very short expiration deadline before reviewing the remaining offers.”

Two dream homes.

Gone.

Anyone would begin wondering if the right house even existed.

Eventually, she, her mom, and I toured a fixer in a completely different neighborhood.

When we finished, she asked what I thought.

“I don’t think you should buy this house.”

Then I said something even more important.

“I think it’s time to change your imagery.”

After losing two homes, fear had quietly become part of her search.

Instead of looking for possibility, she was preparing for disappointment.

I knew better.

We talked honestly about what she truly wanted in a home. If she wanted to expand into a different neighborhood, we’d need to adjust some of the expectations that were no longer serving her.

She embraced that conversation.

The very next home we toured stopped all of us in our tracks.

After more than twenty years helping buyers and walking through thousands of homes across the Portland area, I don’t say this very often.

It was exceptional.

She saw my excitement immediately.

Her family felt it too.

This time I smiled.

“You’re going to be the buyer who writes the outrageous offer.”

There was another offer deadline.

This time…

We ignored it.

Most people would question that strategy.

She trusted me.

This week she’s closing on that home.

And I don’t think she’ll regret it for a second.

Sometimes making it home requires swinging for the fences.

One of the greatest lessons I’ve learned after helping hundreds of Portland buyers is that success is rarely a straight line.

Sometimes the first dream disappears.

Sometimes the second one does too.

Sometimes the biggest obstacle isn’t the housing market.

It’s the story we begin telling ourselves.

As we move into summer, I’m reminded that all of us have the opportunity to redefine what we want to create. We don’t have to let past disappointments shape our future decisions. We can choose a new vision, a new strategy, and sometimes, take a much bigger swing.

Whether you’re buying a home in Portland, selling your Portland home, or simply navigating your next chapter, I hope this story reminds you that setbacks don’t always mean you’re on the wrong path.

Sometimes they’re simply leading you somewhere even better.

If you’re thinking about buying or selling a home in Portland or Southwest Washington, I’d love to help you create a strategy that fits your goals—not just the market.