Failure, Practice, and the Importance of Real World Trial and Error

We all want to get better at the important things. Become better at our core offering, of course. Become a better person, certainly. Maybe even get better at taking care of ourselves, since that’s the skill that underlies a great deal of achievement elsewhere.

So it seems odd that the commonly accepted methods of getting better are not more widely adopted. I’m talking about practice.

We read a lot about how to make improvements, the best improvements to make, and how to do them… but that tends to be where it ends. So I try, as much as possible, to be active in making meaningful improvements based on what I learn.

An Example

At the beginning of October I launched the #onething challenge. It was based upon motivational theory. Racking up small wins, and sharing those wins with others, is a powerful motivator. The idea was that every day, you would designate one thing to be your primary goal, whatever made sense for your business.

I wanted to build momentum. One of the things that bugs me about my productivity style is that I’ll spend three-four days getting nothing in particular done, and then a couple of days that makes me look like a productivity rock star. I’m a methodical person! I thought. Why am I so haphazard about my execution?

So, as I created my own #onething challenge, I created for myself a “no wiggle-room” goal.

According to Switch: How to Change When Change is Hard, a “no wiggle-room goal” is for those times when the problem is particularly hard, or buy-in is not a given, or when there’s a tendency to move the goal posts in such a way as to guarantee gold stars. For motivation to work, it’s important to feel a sense of accomplishment– but if your sense of accomplishment outstrips your progress, that’s not good either. So to get around that issue, you create a ticky-box goal. You either accomplished it, or you didn’t. It’s black and white.

Practical Information

The good thing about the vast wealth of information we have available is that you can learn about all kinds of things– in theory. But although I’ve read up on all kinds of motivational theory, it’s still just information. In practice, things can be much different.

For instance, we all know that we need to eat right and exercise. That’s all you have to do, and you’ll prevent most health problems. So that’s what you do, right?

It’s a lot harder in execution. In real life, there are forces that make it hard to choose the right foods. You can be fully willing to exercise– only to find out that there’s not really a good time in your schedule to get sweaty and have to shower and do your hair and makeup all over again… which might mean that working out has to be very, very first in your day (which means you have to rearrange your life to get up earlier) or very last in the day (when your motivation is depleted.) A lot of things are far more complicated in execution than we had expected, and it takes time to get each obstacle under control.

Be Willing To Fail. A Lot.

The corollary to things being complicated in execution is that you have to be willing to fail. This was the single hardest part about the #onething challenge for me. There were MANY days when I failed in my no wiggle room goal, and a couple where I even rage-quit because the goal was so antithetical to what I knew needed to be done. (This was the fault of how I defined my “no-wiggle-room” goal)

I learned a few things from this.

First, I squirm like a worm on a hook when I have to admit I didn’t do something I said I would. For years I’ve had a practice of not allowing myself to publicly commit to things I wasn’t positive was a high priority, and by defining winning as “shipping” I accidentally boxed myself into a lot of lower-priority tasks. I won’t make that mistake again.

I also learned why my productivity goes in fits and spurts. It’s because I’m laying necessary groundwork without really realizing that I am.

You see, if I were a project manager, I would have to sit down and break out every single step of the project. I would set scope, responsibilities, and constraints and painstakingly record every ounce of information into a spreadsheet.

I don’t have the training to do that. But it still needs to be done, and that’s what I’m doing. I’m refining the vision that I have for the project, massaging it, breaking it down into stages and steps, uncovering and mitigating obstacles. But when you don’t realize you’re doing it, it looks like a person trying to set up the perfect Trello board. I wonder how much of what people call their perfectionism is just trying to clarify and nail down a blurry vision?

What All This Means For You

It’s one thing to learn. It’s another to execute. It’s a pain in the ass to try and find ways of executing what you’ve learned in books to real life, but what the hell are you reading for if not to improve?

It’s also an enormous opportunity to stretch yourself. The stuff in books? It might not work in real life (a lot of stuff doesn’t. Ever read a romance novel sex scene?) Your failure rate is going to go up, absolutely. And that’s exactly what you want.

Your business is going to run best when you know yourself the way that Joshua Bell knows his Stradivarius. To get there, you have to try a lot of stuff. You have to fail, and succeed, and figure out why what worked, worked, and what didn’t, didn’t. You’re also exercising your skills in a way that day-to-day business doesn’t really allow. This is a NaNoWriMo you can do any time — and should. My old music teacher, when we were working on challenging pieces, had a trick of pulling out an even more challenging piece for me to work on when I was preparing for competition. After a few weeks of tripping over the new piece, I would go back to my competition pieces with a lot more skill. Taking a little time to challenge yourself does the same thing.

Trial and error is the necessary gap between where you start and where you want to be. Make a point to do it. Make a point to push yourself into a little awkwardness and discomfort. You’ll grow a lot faster that way.

What was the last challenge you set yourself?


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