Know When To Walk Away

February 20, 2026

#2 From the “Things I’ve Learned In Business” series.

As business owners we spend a lot of time and energy making things work. We work on our business. We work on deal making. We analyze, calculate, contemplate, and discuss ourselves to death on the final decision of whatever project we happen to be working on. Was it worth it?

There is a statement, a philosophy really, that I have come to believe in. “If it is meant to be it will happen.” I have used that in real estate investing both for my investments and in dealing with clients and their investments. And it actually works for everything- buying a car, taking a vacation, relationships, everything. So why is it so hard to know when to walk away?

Why Is It So Difficult?

We become emotionally invested in outcomes. No matter what it is, we get involved emotionally in the outcome. That’s why I stay away from residential real estate as an investor and as a broker. The buyers and sellers in residential transactions are EXTREMELY emotional about the properties and the deals. That emotional involvement causes people to make bad decisions, use bad judgement, and stay in a deal way beyond the point when they should drop out and walk away.

My Latest Experience

Today was a great example. My wife and I tried to record a podcast episode for our new video podcast. It wasn’t working. The equipment wasn’t working and the lighting was bad. It wasn’t that it was not perfect, it sucked. We made two failed attempts at recording because apparently when you get frustrated it gets more and more difficult to talk. Our third attempt went better. We recorded a 19 minute episode and were happy with how it went. Sort of. Then I got to the editing process. Obviously our sound equipment must have been possessed by some kind of electronic gremlins. It was all unusable. That’s when I decided it just wasn’t meant to be. Ditch the emotions and walk away. That was the only thing about that recording session that felt right.

Clues

The same goes for all business dealings. Our feelings will give us clues about a deal. Not emotions. Feelings. They’re different. Intuition, past experience, a feeling of familiar circumstances can all help you make your decision to stick it out or walk away. It’s that feeling you get when the math doesn’t quite work out the way you want. When the income the deal generates is tempting but it’s just a little too close to the expenses. The temptation for the money is your emotions working on you. The feeling you get from the math is your intuition and experience.

Don't Look Back

Once you walk away from a deal you’ll be tempted to look back. Don’t. I’ve been in many discussions other investors about the deals we’ve walked away from that we regretted. Don’t live that way. Be happy that someone else took the deal and possibly did well with it. Maybe the deal was for them and not for you.

So that’s my little piece of past experience from real estate deals and business decisions from over the past few decades. I hope it helps someone somewhere with something they might be struggling with.

Just remember sometimes you just have to know when to walk away.

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