Fail More Gooder than the Before Time

Crazy Talk

I have a crazy, controversial attitude toward success: I feel good when I succeed, and I feel bad when I don’t succeed.

Wait, no, that’s not the controversial one. Sorry, got my notes out of order.

I appreciate failure. There we go.

Now, I know this isn’t actually controversial; people constantly offer advice about learning from mistakes and treating setbacks as a chance to grow. But I have a specific idea which became important to me in the past few years, that I wish I’d understood long before. This isn’t a groundbreaking new insight, but maybe hearing it in a new way will help you appreciate it, if you didn’t before.

First, a confession: I’m going to tell you about how I’m dumb. Don’t worry about my self-esteem. I know I’m awesome. I also know I’m dumb. Let’s take a look.

Think Harder

Here’s something dumb that I used to do all the time: If I didn’t know how to do something well, I didn’t try to do it at all.

I’m not talking about perfectionism, per se, but a very similar attitude. When I approached a difficult problem, I always wanted to spend a lot of time up front, thinking through how to approach it before actually working on the actual task. I never said it out loud, but I always had this underlying assumption that if I spent long enough just thinking, then I’d get this flash of inspiration and I’d realize exactly what to do. So I’d pace around or take a walk or sit down with a journal, and I’d say to myself, “Self, we’re going to sit here and think about how to do the thing until we have figure out the best way and then we will do it the best way and the thing will be done and we will be heroes.”

And we’d think, Self and me, and we’d ponder and mull and contemplate and consider and we’d stare very intently at our conspicuously blank journal until eventually realizing that wanting it harder didn’t make things easier and we’d give up and go play Nintendo.

This process has never worked once in my entire life.

Here are two and a half problems with this plan:

  • I never actually started the task
  • I got mad at myself
  • I got meta (this is the half)

You Wanna Start Something?

Simple productivity rule: in order to complete a task, you have to actually do it.

The biggest, most significant problem with spending too much time thinking about how you work is that you’re taking time away from actually working. And of course, a major disclaimer belongs here: thinking about how you work is good. You should ask yourself if there’s a better way to do it than the way you’re doing it now. But don’t miss the forest for the painstakingly manicured trees. Split your time! Spend a few minutes asking questions like “What do I need to do first?” and “How can I break this down into smaller chunks?” and “Is there a good technique for this?”, come up with some basic answers, and then roll up your sleeves and get started (unless your task is to put on a sleeveless shirt).

After you’ve made some progress, go back to question mode. Ask yourself “What did I do poorly?” and “Did I miss anything?” and spend some time looking for ways to do it better. This isn’t about blaming yourself for mistakes. There’s a huge difference between asking “Do I suck?” and saying “I can be even better.” This is about being even better.

Mad is For Hatters, Which You Aren’t

This one’s pretty simple: trying to do something that doesn’t work will not work. This is an important part of appreciating failure, like I mentioned before: when you fail and learn from it, you make a change, and you abandon the thing that doesn’t work. Don’t lose yourself in trying to do everything right the first time, because you will get mad at yourself and end up in a downward spiral where you try harder and fail harder and try harderer and fail even more worser and you get so angrified that you stops using your grammars good.

Take it from me, don’t bother learning this one the hard way.

What’s a Meta With You?

The best thing about realizing your planning method doesn’t work is when you use your broken method to try to fix your broken method. I was stuck for longer than I’d like to admit before I understood that thinking long and hard about how to think long and hard wasn’t getting me anywhere.

Remember that thing where I’m dumb? Yeah, me too.

So What Should I Do to Do What I Should?

Most of this post has been about what not to do, but I want to close with some basic advice for good ways to get things done.

Most importantly, start. Ask a few questions, gather a few supplies, do whatever seems obvious and readily available to make the task easier, but you usually don’t need to rally the troops and deliberate before you make some progress. You’ll even find that having something to show for yourself early on gives you something to reflect on when you want to improve it.

Second most important, iterate. Software development has adopted the idea of version numbers. The vast majority of software releases are not Version 1.0 – they’re 1.1, 1.5, 2.0, 10, and so on. We start with something that’s good enough, and then we use it for a while, and we update it when it’s no longer good enough, or when we realize we can make it even better.

Third, software developers also have a concept called minimum viable product. Remember your first cell phone? I bet it didn’t even have Angry Birds on it. But it could make phone calls! Start with something that does the main thing, and make it better as you go.

Rock On

In closing, bear this in mind: You are awesome. You might also be a little dumb. That’s okay! When you catch yourself being dumb, just smile, laugh, and be less dumb the next time. That’s all any of us are ever doing.

What do you say?


One thought on “Fail More Gooder than the Before Time

  1. Anna Spooner says:

    AWESOME post! Thanks for the playful, fun advice about a topic most of us find decidedly un-fun – failure. :-)

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