General George B. McClellan was a brilliant planner, but his overly cautious style may have tacked years onto the U.S. civil war. Lincoln became frustrated, commenting with devastating wit that “McClellan is always almost ready to fight.” Eventually McClellan’s risk aversion forced Linoln to relieve him of command, after sending a telegram that read, “If General McClellan isn’t going to use his army, I’d like to borrow it for a time.”

Contrast Colin Powell, who recommends: “Once information is in the 40% to 70% [certainty] range, go with your gut.”

I don’t recommend that you take stupid risks, that you make no effort to gather data, or that you spend your political capital carelessly. But I do recommend that you follow Powell’s example, not McClellan’s. To quote Powell again, “You don’t know what you can get away with until you try.”

Thomas Edison tried 1000 times to invent a light bulb before he succeeded. Why do we expect in software to get our designs right on the first attempt? I submit that if you aren’t losing a battle now and then–if you don’t make any failed experiments–you are not working smart enough or courageously enough.

If you don’t lose the occasional battle, you will never win the war.

Losing an occasional battle keeps us humble. It means we’re grounded in reality rather than ivory tower imagination. It means we value balance and pragmatism over theoretical perfection, and it helps build a healthy regard for the needs of other people.

Go try. A lost battle of the sort we fight with software is never an Antietam or Gettysburg.

“To live a creative life, we must lose our fear of being wrong.” Joseph Chilton Pearce.

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