Are You Playing to Win . . . or to Not Lose?

I had a great chat with a founder friend recently. We connected years ago when I was an early founder. He’s super successful and has built a bootstrap company that does tens of millions of dollars in revenue annually. Our early chats helped me think bigger about my own start-up.

We talked about psychology and the outsize impact it can have on outcomes. How a person thinks about what they’re doing has a much bigger impact than most people realize.

A big takeaway from our chat is the difference in approaches people have when they’re building something and how each person’s way of doing things is heavily dependent on their psychology. Some people limit themselves by focusing on the downside. Failure is terrifying to them, and they want to avoid it. Their focus on not failing affects their decisions and actions. They try to mitigate every downside, which leads to more conservative and protectionist decisions. Said differently, they play to not lose.

Some people believe there are no limits to what they can achieve. They see things differently than most. Their focus is sharply on the upside: on winning, being the best, building something big, or however they define success. They see a big opportunity and make every effort to capitalize on it. They usually make swing-for-the-fences decisions—bold ones, with lots of risk but also the potential for huge upsides. The risk associated with the decisions they make would terrify most people. Said differently, they play to win.

Entrepreneurs are generally considered to be risk takers, yet both psychologies can be found among successful entrepreneurs. There isn’t a right or wrong psychology, because you can be successful with either. The big difference is the magnitude of your success. Entrepreneurs who have had outsize success tend to have a play-to-win mindset.

What are you doing, psychologically speaking? Playing to win, or to not lose?