Not long ago, some new friends invited us over for dinner. We were eating some chips and salsa before the meal, and one of their kids came through the room and overheard the dad say something about a big project of his that had flopped. The kid then blurted out, rather loudly: “My dad fails a lot.”

I responded with the first thing that came to mind: “That’s fantastic!”

Failure is an option.

If, like Tsh, you’re hoping to risk more this year, I want you to get chummy with a friend of mine: failure.


Here’s the part of the post where I dress failure up in fancy words that make it sound glorious: Failure is an opportunity for grace, nobility, and a re-focused sense of purpose.

Hahaha. Okay. Now that’s over (whew!), here’s the part of the post where I’m more honest.

Let’s be frank: failing is brutal. It’s deflating. Depressing. And the bigger the risk, the bigger the failure … and the bigger your hesitancy to get back on the horse. I think “celebrate failure” is actually fairly hollow advice, so please don’t think this post is saying “yay, failure!” It’s not.

But failure is a handy proxy. It’s a side effect. If you’re trying new things, and those new things are outside of your comfort zone, you’ll end up failing at some of them.

When you fail, you can learn. And when you don’t fail, by definition: you’ve succeeded! At that thing! That was kind of big and unknown and a bit scary!

In both cases, you can push yourself a bit harder next time.

So it’s not that failure is, itself, a good thing. It’s that failure points to other things — challenge, growth, adventure, experimentation — in your world.  And those are good.


How to fail well

One of the big dangers of risk-taking is that you’ll succeed and won’t know why. One of the nice things about failure is that you can often pinpoint where things went wrong.

“I should speak up earlier next time.”
“I should’ve re-measured that angle again before I cut the wood.”
“Maybe two hikes in two days is a little too much for us.”
“I should’ve spent more on the higher-quality version of this thing, instead of going for the cheaper one (that’s now broken).”

Unless you make note of what went wrong, though, it’s easy to let the lessons pass you by. Your failures are whispering to you. Listen to them!

So how can you fail more, and fail in a way that you can learn, so you can then have better successes down the road? Here are a few ideas.

Get a fail buddy.


You probably have a friend or two who you see every once in a while where you sit down at their kitchen table, you both sigh, and one of you says “so how are you?” Or something similar. Think of that person. Got it? Perfect. That’s your new fail buddy.

  • From now on, before the end of the first cup of coffee, you have to both share something you’ve tried and failed at recently.
  • Before you pour the second cup, you have to share what you’ve learned from the failure.
  • Before you finish the second cup, you have to share something you’ll try before you hang out again.

We don’t like to talk about failures because they feel like a moral failing. Like we’re a bad person because we messed up. Having a friend who’s also pushing themselves in difficult ways makes failure less stigmatizing.

Keep a fail log.

You can do this in a number of ways, but the easiest is to take what you currently use to write notes and just create a new one of those. I really like Evernote, but the medium doesn’t really matter as long as it’s one you’re comfortable with.

As you go through your day, keep a running log of the things you’re trying. Every time you learn something from a failure, write down two new lines.

  1. Line one should start with “Failure:” Write down what happened.
  2. Line two should start with “Lesson:” Write down what you learned.

Even if you haven’t figured out the lesson quite yet, at least start the exercise by writing down the failure. A lesson will come to you. Promise.

Show your kids that failure’s okay

Those of us with kids want them to “succeed.” I’m on board with that. Absolutely. But if the only goal we’ve given our kids is that they “succeed,” they’ll be poorly-equipped to handle failure. They won’t push themselves, because either they won’t want to fail, or they won’t want to let you down. They’ll live too-safe lives.

I’ve heard that one of the things pediatricians look for during checkups is scrapes and scabs on kids’ knees. They’re a good sign. They show that the child is pushing herself, learning to run, and jump, and play, and sometimes that play exceeds her capabilities.

Teach your kids that failure’s inevitable when you’re living life. Teach them that learning from failure isn’t inevitable, but that it’s something they can learn to do well.


Go forth and fail

I hope your 2014 is a year of adventure, risk, and experimentation. And I hope that, along the way, you leave some failures in your wake.

That new recipe you’re not sure if you’re up to trying?
Make it.
That craft project you’ve wanted to try but you worry about how it’ll turn out?
Do it.
That friendly-looking person at the park about whom you’ve thought “Friend?”
Say hi.

Put yourself out there, don’t be afraid of failure, and don’t be afraid for the people in your life to think about you: “They fail a lot. And it’s fantastic.”

I’d love to know: When you fail at something, are there any tricks you have for learning from them? Are there any lessons you’ve recently learned the hard way (and are brave enough to share)? Have you recently succeeded at something, despite being pretty sure it wasn’t going to work out?