Making Mistakes

(MoneyWatch) I was doing puzzles with my 5-year-old last week when I noticed something -- he seemed wary of trying pieces in different spots if he wasn't sure he'd be right. Even though our Scooby-Doo jigsaw was definitely a no-stakes exercise, he viewed a piece not fitting the first time you tried it as being "wrong, and being wrong is bad.

As I tried to counter this mindset -- "just keep trying different places, sweetie, that's the fun of puzzles!" -- I realized that many grown-ups probably struggle with the same thought process. You decide not to contribute an idea in a brainstorming session because you're not sure it's a great one. You come up with reasons why a new client won't hire you before you've even asked for her business.

Maybe you're right on both occasions, but over time this is obviously a limiting mindset. Here are some reasons to try to fail more often:

1. Good ideas are often a numbers game. Your chances of stumbling upon a 1-in-100-level idea are much better if you come up with 100 ideas -- including 99 bad ones -- than if you come up with three.

2. Knowing something doesn't work is a valuable insight. I've floated potential book concepts in blog posts before. If few people comment or forward the post, I know I'm barking up the wrong tree. That's a good thing to figure out before investing more effort.

3. You get better with practice. After doing enough 100-piece puzzles with my son, I was starting to see which pieces might fit just by shape. I tried explaining to my son that few people are "good" or "bad" at puzzles -- you get better by trying different things and seeing what works. If he tried pieces, and then thought about why they didn't work, he'd get faster at finishing puzzles, too.

4. "Perfection" is usually impossible, or pointless. Great hitters still strike out. The point of puzzles is the challenge of assembling them. Humans are happiest when fully absorbed in tasks that are difficult but doable. That means you're probably not getting everything right. If you are, your work is too easy -- and that's no fun.

5. Sometimes you think you'll fail... and don't. In the summer of 2001, I was an intern on the op-ed page of USA Today. I had an idea for a column, but assumed the editors wouldn't be interested in something from the person charged with emptying outboxes (remember those?) Nonetheless, I figured I should at least mention the idea before sending it elsewhere. They wound up running the piece, which led to all kinds of wonderful opportunities later. If I'd never risked a no, that wouldn't have happened.

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