How to fail

Convincing Failure

There are two ways to fail and the consequences are orders of magnitude apart. Convincing failures allow us to make better decisions in the future. We tend to agonize over the risk of executing something poorly but the much bigger risk is building the wrong thing to begin with.

This is one of my favorite articles about Failure. Written by Andrew Bosworth, almost a year ago now (who I wish would blog more), I still reference it from time to time to remind myself of the lesson in it, which is …

“… if you execute to a level of quality that makes it unlikely that another team, even with more time and effort, could succeed, then yours is a convincing failure. This kind of failure is strategically valuable because we can now eliminate an entire development path from consideration. That means subsequent work is dramatically more likely to succeed. A convincing success is unquestionably the goal of every effort, but a convincing failure should be a close second.”

For me the lesson that lies inside of that nugget doesn’t just apply to Engineering teams, it applies to life.

Lots of times, people will try something, but they’ll do it half heartedly. They might open a business, or try to do standup comedy, or try to make a pro team (that was me), but they don’t give it their all … maybe they want to string some wins together so that they can convince their friends and family that this isn’t some flight of fancy, or maybe they’re afraid that they’ll fail, so if they don’t give it everything they’ve got, it won’t hurt as much when things don’t work out. The problem with this approach is that, just like the article says, you’re still left wondering “what if?” when the opportunity finally fades from view. Which in a lot of ways is worse than not trying at all.

I like reading this article because it reminds me that if I try something in my personal life, that I want to either succeed or I fail … hard. No in between.

about not compromising your truth …

The for-profit sector is no different. People at all levels, especially management, witness the slow undoing of good customer service, product quality, or safety standards, and they don’t say a thing about it. Even if it violates their own value system and the mission of the company. But if everyone at a crummy airline, for example, had the same zero-tolerance for bad customer service as a lesbian has for lying about the fact that she’s married to a woman, it wouldn’t be a crummy airline for long


Never Lie About Who You Really AreYesterday was my 12-year anniversary of being with my partner, Jimmy. I called a florist, and a nice woman picked up. I told her, “It’s my anniversary, and I want to send roses.” I know she’s thinking the roses are going to a woman.

via Hbr