Err on the side of action

Last weekend I was in Boulder for a wedding. For weeks I’d been looking forward to going climbing while I was back in Colorado. So on Sunday some friends and I headed up Boulder canyon to climb some rocks. We debated before leaving whether the dark clouds were going to be an issue, but we decided to go anyway. As we drove up the canyon, rain drops began to fall on our windshield. We kept driving. We reached the trail head and pulled off on the side of the road. The clouds were grey all around and the rain was light but unyielding. We started discussing whether to hike up to the crag or to go back and play board games or something. Wet rock isn’t much fun to climb, but we were torn. We didn’t want to turn back if there was a chance of it clearing up, but our group was split on what to do. I threw out my vote: err on the side of action.

“Err on the side of action” is really just another way of saying “regret the things you do, not the things you don’t do”. I’d rather get soaked in the rain and have a failed climbing trip than turn back without giving it a fair shot. People tend to overestimate how much regret they will later feel from their decisions. Research suggests that people are remarkably good at avoiding self-blame, and are better at avoiding regret than they realize. Forgetfulness and selective memory are a part of being human and sometimes it can be a blessing. Nostalgia has a way of making us forget the bad. We remember the “good old days”. We remember college as the best time of our lives, or that relationship that seems so perfect in retrospect, even though you had all sorts of problems at the time. Grab life by the horns and don’t worry too much about doing stuff you might regret.

Making the decision to err on the side of action can also be a useful device since there are so many things that are good for you, but you won’t feel like doing them in the moment. Exercise is an easy example. You don’t feel like going for a run, but you’ll feel better if you do it. Perhaps you don’t feel like going out and being social, even though that’s the one thing that would cheer you up. Make the decision ahead of time to say “yes” to the things you want as part of your life. There’s a chance you’ll do something you’ll genuinely regret, but optimizing your life for the least amount of failure or regret is a pretty horrible way to live.

One of my favorite quotes is from Michael Jordan:

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

In an interview at New York’s IAB conference, Facebook COO Sheryl Sandberg said “We’re more afraid of losing by standing still”. Big companies often fall into the “safe” position where they feel like they have so much to lose that they don’t take enough risks. It’s neat to see Facebook so committed to erring on the side of action. They admit that they’ll make mistakes, but as Marc Andreessen said “If a company is hitting more than 50% of its goals it’s too conservative”.

I’ve missed a lot of buses over the years. I get impatient waiting for them and just start walking in the direction they are going. I always hope I’ll time it right so I’m within sprinting distance of the next stop whenever the bus finally shows up. It doesn’t always work out for me, but I’d rather be proactive than just stand around.

Don’t be scared to fail. Be proactive. Err on the side of action.