Lately I’ve been struggling with Yoda’s immortal words, “Do or do not … there is no try.” So many startup/tech writers have referenced that quote: Jason Baptiste … 37 Signals … half the people on twitter. Brad Feld even wears an uber-nerdy version of it on a t-shirt.

I think Yoda’s trying to tell me not to give myself permission to fail, but I don’t think I do that much. I have a bigger problem restricting myself only to activities where I know I’ll succeed. An aversion to risk aversion even led Seth Godin to question Yoda’s wisdom in Poke the Box. There is something about trying that’s important; it moves us forward.

Maybe Ash Maurya has figured out the riddle. After reading Running Lean and talking with Ash recently, I started to realize that everything Ash does is an experiment. He doesn’t say, “I’m trying to start xyz” – instead he says, “I’m running an experiment to find out something about xyz.” In his businesses, in his blog, in his book, even talking on the phone, Ash really appears to think and act that way. Oh … and Ash channels Yoda, too.

This is changing the way I think about change. An experiment is not a “try” – it’s a “do.” Running an experiment is an affirmative action. The result may or may not be what I wanted or expected. Doesn’t matter. What matters is that I did it, that I ran the experiment and gathered information about the world as it really is.

I recently noticed that eating better makes me feel better. I could get caught up in thinking “I will try to eat better” (or even worse, “I should eat better”) … or I could just eat better, as Yoda would undoubtedly suggest. But “just do it” sometimes leads to a distracting battle of will with myself, so instead of testing my willpower, I’m looking at my diet as a long-running experiment. What happens when I eat a grapefruit as a midafternoon snack instead of chocolate? Does a single beer at night really affect the way I feel in the morning (dammit)? Drinking water instead of soda at lunch feels less like giving up something and more like “doing” when I think about it as an experiment.

How about my career? There are lots of things I want to do that I haven’t done. Write more. Present more. Create a “MicroISV” like Patrick McKenzie or Rob Walling. Have a big impact within Microsoft. All of these “goals” are too vague to act on. So I’m starting to ask, “What experiments can I make to move forward, to help me learn something about these points on the horizon I seem drawn to?”

Take writing – at the beginning of the year, I told myself I would (should) write every day. I have not. For a while, I thought it was merely a matter of will or time management, but I know that’s not it. It’s fear – fear of finding out that I’m not a good writer. Who cares? If what I write sucks, then nobody will read it. Simple as that. Nobody will be hurt in the process, and I will find out something. I may even get better.

I’m consistently reminded about a story I heard on NPR a few years ago about Quantity vs. Quality from the book Life is a Verb:

A college ceramics teacher decided to do an experiment with his two fall pottery classes. He told one class they would be graded solely on the quantity of work they produced that quarter and their grade depended on the number of pots they threw — so the more the better! The second class was told their grade would be determined by the quality of their work and they only needed to produce one “perfect” pot.

Who did better work? The better quality pieces came from the class that was graded on quantity! As they were making all those pots, they couldn’t help but get better at it. They were doing, not thinking or trying. People are naturally curious. I suspect that each pot a student made became a little experiment in pot-making, whether they knew it or not.

I do a podcast with Bob Walsh. We just published our 103rd show. A hundred and three! And I still think it’s no good … thank goodness Bob keeps pushing us forward. If I did the show on my own, I probably would have 3 shows done. Every time we publish, all I can think about is what’s wrong with it or what needs to be better. Yet we have more than a thousand subscribers, and people I really respect tell me they listen to it and get value from it. Yes, there is still work to be done, but maybe it’s time to stop worrying about being a good podcaster and start looking at each show as an opportunity to run an experiment in podcasting. We can’t help but get better if we give our best, evaluate honestly, and keep doing it.

Isn’t play just a series of experiments? Kids don’t think about it, but they’re running experiments constantly. What happens when I poke this box … or when I stomp in this puddle? I’ve never considered myself a particularly playful person. Maybe being more experimental will induce some playfulness.

Heck, it even applies to romance. I’ll never forget a conversation I had with a friend way back in college:

Bryan: Foley, how many times have you ever been slapped?
Me: I’ve never been slapped!
Bryan: Well, then you’re doing something wrong …

I never understood what he meant, but I think I’m beginning to. Turns out that women don’t generally like pigs, but they don’t usually like men to ask for a permission slip, either. A little experimentation with your partner or potential partner can take you a long way. Of course it can get you slapped, apparently, but the point is … you have to be willing to take some risks.

Tomorrow I’m running a dubious experiment. I’m going to find out what riding a time trial with zero training does to my body. It’s dubious because there is a large body of evidence from other riders pointing out what will likely happen. It would be a more interesting experiment to find out how training effects my personal performance. Instead of getting mad at myself for what I haven’t done yet, I’m just going to have some fun in the saddle and watch the experiment unfold.

As Yoda says, “Try not! Do or do not … there is no try.” When you find yourself merely trying, consider running an experiment instead.