How to Be Really Good at Losing

I’m telling you this story because playing squash made me face my demons. I had never felt that I was built for that kind of sport so I had avoided racquet sports my whole life. In a way, I was always winning—simply by never playing the game. Once I started taking an active role in overcoming my lack of knowledge and skill, it became apparent that I could actually succeed. That first step is always the hardest. To take it, we need to become way more comfortable with losing.

Losing, but Still Winning

Innovation involves a lot of losing. I know that completely turns the common view of innovation on its head, but it’s none the less true. I have written before about how the majority of innovation does not involve coming up with new things, but reimagining things that already exist and connecting them in new ways to accomplish something that had previously failed or had never even been thought of. What most people rarely talk about is that a successful innovation typically happens down a road that is literally paved with loss. Even if they do talk about losses, the one piece that needs more discussion is how losing teaches us to deal with the emotional aspects of losing. Losing is a terrible feeling, and it does not get any better no matter how many times it happens. Sometimes that emotion involves realizing you were not as good as you thought you were, so it’s a humbling experience that can be hard to digest.

Sometimes that emotion is all about realizing your ego and arrogance far outstrip the skillset you thought you had. When we believe that we have seen and done things long enough to have risen above the little things that are often necessary for success, we put ourselves at a major competitive disadvantage that permeates throughout everything we do.

To become good at coping with loss, we must first deal with these emotions, which can actually take some time to process. Instead of doing the common post mortems that happen when you lose a project or a customer, spend some time processing the actual emotions that you are feeling. We often tend to skip over that crucial step to learning. I know I sometimes do this still, and it remains the hardest part of recovery.

In general, it is good business practice to learn from losing and to be good at learning from losing. On a global scale, human society is relatively uneasy with failure. Even the word I just used—failure—may have made many of you who are reading this column feel a bit uneasy. However, we should not sugarcoat that word. Instead, we should draw strength from it. I have failed many times and at many things that I have tried to do. Losing has always been and still is tremendously difficult to deal with. I know I do not always handle loss in the way I should. However, as part of the innovation process, we know that learning from loss keeps us agile and enables us to deal with challenges in the future.

Uninterrupted winning is not only a fantasy but one that prevents our being able to manage change. What’s worse, it’s a barrier to our being able to adapt and figure out new approaches that would work.

Learning from loss—and taking inspiration and insights from others who have lost as well—gives us the ability to recover our losses and also embodies within ourselves a tremendously powerful tool. Failure, in the end, creates an exceptional environment for our improvement and ultimate success in life—both personally and professionally.