A Costly Lesson in Readiness

By: Teresa Loos-Tedrow | Co-Founder | Next Legacy Group

I injured my back playing pickleball.

Day one. Five points into the match.

I hadn’t played since high school, but apparently my brain skipped that detail and went straight to athlete.

So I did what any former teenager trapped in an adult body would do. I jumped as high as I could for a ball that was way over my head.

To be clear, this was not a moment where someone’s kid’s college scholarship was on the line. This was recreational pickleball. The stakes were absolutely nothing.

When Overconfidence Meets Reality

I strained muscles in multiple places in my back. And because I’m consistent if nothing else, I kept playing. Then I went back the next day too.

The Lesson: Pretending You’re Ready Is Expensive

The ball wasn’t the problem.

The story I told myself was.

“That’s makeable.”

“I’ve got this.”

“Let’s go.”

That same thing shows up in real estate investing more often than people like to admit.

How This Shows Up in Real Estate Investing

It sounds like

• “We’ll grow into the debt.”

• “Rent increases will cover it.”

• “Expenses won’t move much.”

• “We’ll refinance before it matters.”

Sometimes you get away with it. Sometimes you play through it until it stops being funny.

What Smart Real Estate Investing Actually Rewards

Real estate doesn’t reward the highlight reel. It rewards durability.

• Margin through cash reserves and breathing room

• Stress testing assumptions with higher vacancy and expenses

• Discipline in knowing when to let a deal go

Because the goal isn’t to win a single point.

The goal is to stay invested year after year without relying on luck to survive.