One of my favorite books on technology is “Pride Before The Fall” by John Heilemann. It’s about the Microsoft antitrust trial in the mid 1990’s. Heilemann got unprecedented access to the players involved like David Boies, Joel Klein and Bill Gates himself.
One of his main points was that this was the first time that Gates really experienced failure or defeat. And he took this failure so deeply and personally that he just wasn’t the same person afterwards. I forgot where I read this but Heilemann observed that Gates’s body language and demeanor changed after the trial verdict. He just wasn’t the same person - deflated, defeated. The long run that he had without failure turned into pride or hubris. And whether this is correlation or causation but one could argue that Microsoft’s record of innovation really came to a standstill afterwards. Gates retired as Microsoft CEO in 2000.
People often talk about how failure is accepted and even celebrated in Silicon Valley. That it’s almost a badge of honor. I think about this a little differently. Personal failure can be debilitating. It’s like getting your heart broken for the first time. It’s someone telling you that you’re not good enough. It’s about feeling exposed or feeling a deep sense of loss, embarrassment or humiliation. If you read stories about how Steve Jobs or Jack Dorsey describe their “failures” or “defeats”, you get almost a visceral sense of what they experienced. Or watch this video where football great Tom Brady cries thinking about his failure when he was overlooked during the NFL draft nearly fifteen years ago:
It makes sense intuitively that this type of ‘failure’ or defeat can be a catalyst for great success. You understand that there are times where no matter how hard you try or how hard you work, sometimes you’re not good enough. If success without failure breeds pride, then failure can foster humility, drive and true self-confidence. The flip side is that failure can be so debilitating that people don’t want to experience it again. And some people never are the same once they experience it.
On a personal note, I think about this a lot when it comes to raising our daughter. I think about the person I want to help raise. Like all parents, I want her to be kind, humble, hard-working and (ultimately) successful. And on the one hand, I want to protect her from everything I mention above - heartache, pain, rejection, and failure. Almost like a porcelain doll that I don’t want to break. But I also know that she needs to experience these things - and probably earlier in life rather than later - to be the person I want her to be.