Hindsight as a Learning Tool

As a founder, I made tons of mistakes. (I often refer to this as stepping on landmines.) Recently I shared one of my more painful stories with a friend. He asked a few questions about why my decision proved incorrect, which I answered. He felt the flaws in my decision should have been apparent from the start and couldn’t understand why I’d made that decision.

The old saying that hindsight is 20/20 is true. Things are often crystal clear when you look backward. You usually have the benefit of complete information. Being in the middle of a situation is very different: you have imperfect information and, often, time constraints.

I explained to my friend what I had perceived the situation to be as it was unfolding versus what I later learned had actually happened. He then understood.

Making decisions with imperfect information is hard, and I’ve gotten it wrong lots of times. I try to make the best decision I can with the information I have. When I finally have the luxury of hindsight, I try not to focus on the outcome. Instead, I aim to learn. In my experience, regardless of the outcome, there’s always something to be learned when you can see everything more clearly.

Hindsight shouldn’t be used to second-guess or critique past decisions. Founders should be careful not to fall into this mental trap. It’s better used as a tool to help people understand what worked and didn't work so they can improve future decisions.