On failure, pain, and trying again

"I tried again.
And I tried again,
and tried again.
Tried again. 
Tried again. 
Tried again.
Tried again. 
Tried again.
Tried again
… and I could do it!"

Mark Twain, 1907


This might be my one of my new favourite poems.

To be honest, it’s not Mark Twain. That’s unscripted honesty from our four-year-old kid. So simple, and yet so profound.


We first filmed for this in July, the day Ashna got her new pedal bike. I had grand ambitions that we’d assemble the bike in the morning, and by the afternoon, she’d be riding it with a smile. And I’d have it all captured!

Spoiler alert: It didn’t go that way.

The bike was harder to put together than an Ikea bed-frame with built in drawers. There was 20-some pieces and like three pictures. This was the guide:

Step 1. Unwrap bike
Step 2. Put it all together, and make you don’t screw up the brakes.
Step 3. Done. (Unless you’ve screwed up the brakes. Then, see step #2).

From there, the day only got better.

Picture this: four enthusiastic adults trying to bribe one terrified child to try to ride this green machine without training wheels. Meanwhile, child, is accurately thinking ”This thing is clearly going to tip over.”

After some back and fourth, us adults conceded and added the training wheels. There was some brief relief and enjoyable moments until we learned — to our collective surprise — that bikes with training wheels on do in fact still tip over. Yikes.

The day ended with Ashna in tears. I carried the bike home. It was all a bit too much, too soon. It was not the simple, successful, glorious day of learning to ride a bike. Come to think of it, it wasn’t much fun at all.

Pete Holmes, my new favourite comedian-slash-amature-theologian says this:

“Our experiences aren’t errors in the system. They are, as Ram Dass calls them, our curriculum.

After all, out favorite episodes of Breaking Bad or Game of Thrones are when something happens. Good or Bad. Because we know this will push the character. This will lead to growth, or change, or loss. And we love it.

We know that for these characters, pain is the vehicle that takes them from where they are to where they’re afraid to but need to go. But in our own lives, we resist when something happens.”


That hits home.

While we usually want to fast forward to the glorious end — the story is much better on the way. When we’re learning, and figuring things out.

In Mindset, Carol Dweck says this:

“Everyone is born with an intense drive to learn. Infants stretch their skills daily. Not just ordinary skills, but the most difficult tasks of a lifetime, like learning to walk and talk. They never decide it’s too hard or not worth the effort. Babies don’t worry about making mistakes or humiliating themselves. They walk, they fall, they get.”


Why to kids learn so fast? Apparently, it’s cause they’re not scared shitless of making a mistake.

Want to learn a new language? 
Speak in public?
Do improv, learn to dance, or meditate?

Congratulations! But at first you’re going to suck.

I’m not saying this cause I’ve learned it. I’m just starting to learn. Seeing my kid pick up new skills at lightning speed is one of the most inspiring things I’ve been around (pep-talk poem included).

At work, I get watch Richenda lean into incredibly big challenges—shaping organisations—with big scary important repercussions. The day before she presented recommendations to a board of directors I asked her “How are you not terrified?”

“Of course I’m terrified”, she’ll say. But she’s done the work. Done the practice. Learned from mistakes, asked for feedback, gotten better.

I hate being bad at things. Anything. It doesn’t matter what it is, I don’t like failure. In the moment, there’s nothing worse. The only thing that’s actually worse, is not doing the thing because I was too scared. That actually sucks. So the beginning, comparatively, isn’t that bad.

So that’s it.

I set out to make a happy video about learning to ride a bike… but I’m thankful it didn’t end there. That would have been boring. The conflict of failing, and falling, and getting back up again — that’s the beauty.

And it’s liberating, too. You don’t need to be perfect!

I hope that’s as inspiring to you as it is to me.

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Adventures of Ash & Gary