How Do I Decide?

August 7, 2026

#6 From “The Things I’ve learned In Business” series.

This is a question that comes up any time we are looking at investing in real estate, buying a business or maybe making a career change. There are those who make the decision seemingly in an instant. And then there are those who never actually decide. They just analyze and contemplate. And there is the vast territory of everything in between. It’s a complete spectrum of how people make potentially life changing decisions. So what exactly is the point of the decision? Is it to be successful? Buy the right real estate or the right business and become wealthy? Or is the point simply to not fail? It all sounds a little bit like gambling doesn’t it.

Thinking In Bets

There is a book called Thinking In Bets with the subtitle “Making Smarter Decisions When You Don’t Have All The Facts.” It was written by Annie Duke a successful professional poker player. Now the question How Do I Decide makes more sense. I bring up this topic because I’ve always found it fascinating how and why my clients made decisions about buying and selling real estate or businesses. What I have discovered is that no matter how experienced they are or how successful they happen to be they will, at some point, make a wrong decision. And yet they keep going. Keep in mind the wrong decision doesn’t always mean failure or loss. Sometimes you can take a bad decision and turn it into a good one. And you can make a good decision that is profitable but a different decision would have meant even greater success.

Place Your Bets Please

That means the decisions we make are actually bets. And like the subtitle of the book says we have to learn to make smarter decisions when we don’t have all the facts, just like in Poker. Here’s where it gets difficult. The decision to buy or sell a property or a business is only the beginning. That decision causes a chain reaction of subsequent decisions that can either amplify or undermine the success of the initial decision. It’s actually something that is often overlooked.

Think of it like this:

You buy a business. It’s profitable and you got it for a great price. Everything runs smoothly and efficiently. But as the new owner you begin making decisions about the business. You decide you want to have a more active role in running the business. There is a long time employee who has been managing it for years but you think you can make it better. Maybe you can. Maybe you can make immediate changes and make things more efficient. So you take over the position. Here’s where that decision takes an unexpected turn. The person who has been managing the business has spent years building relationships with the employees, customers, and vendors. The minute you replace that person those relationships could all go away. You might be starting over.

Was it the right decision? You can’t always know. Decisions are calculated risks. We all have to make them and there will always be a certain percentage of them that will be a good decision and a portion of them will be the best decision. And then there will be a certain percentage that will be a bad decision and maybe even a disaster. But we still absolutely have to keep making decisions.

Can We Get It Right?

How do we make sure we always make the right decisions? You can’t. Intuition, timing, experience, and faith will help. Coaches and mentors can help. But there will always be outside forces at work. Sometimes making good decisions means being willing to change course to compensate for those outside forces. We all make good and bad decisions. They just have to be accompanied by adjustments.

Cheers!

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