Messy Journeys and Scruffy Role Models

Tell me if any of this sounds familiar:

• Why am I having such a hard time with this? What’s wrong with me?
• Maybe I’m not smart enough to do this.
• People hired me to do this work, but I’m never going to figure this out. I’m a fraud.

There are at least a couple of common threads with these statements, but I think the most interesting one is that each of these statements is an implicit comparison that I’m making between myself and someone that’s, y’know, good at what they do.

And when you’re trying something new, it can be really hard to remember that you’re trying something new. We approach new things with expectations, adn we typically want to feel smart, we want to believe that we’re good at stuff. Eventually, though, Reality pops in for a visit to remind us that we haven’t done this before.

“Sorry to rain on your parade there, but this… this isn’t going to be a cakewalk for you. Here, have a brick wall!”

And when you run face-first into a brick wall you feel, well, not very smart. Someone else would have noticed that wall. I don’t know what I’m doing.

Desirae Odjick wrote a great article at Half Banked on learning about money that I think touches a bit on this:

“What makes you feel confident with money?”

There’s a lot I could say about it, including that building knowledge over time has been helpful, as has seeking out both expert opinions and people “in real life” who are willing to be open with me about it.

But I did that over ten years, at different paces based on where I was in my life. “Start ten years ago,” isn’t exactly the most actionable advice out there, ya know?

When I’m tackling something new, it often feels like I have so much catching up to do. And, sure, if the best time to start was ten years ago, the second best time to start is right now.

But here’s the thing with comparing yourself to a ten-year veteran in the field, or comparing your first app to stuff that’s won Apple Design Awards or whatever.

They’re not real.

Not really, anyways — at least not outside of the reality you create for them in your head.

Building up the confidence to just get started on something new is hard, and it’s especially hard when you’re comparing yourself to other folks that have years of experience doing what you’re struggling to learn.

And so in your augmented reality that you create for these experts and the fruits of their labour, you can’t see the ten years of hard work. The string of failures. The moments of self-doubt and being on the precipice of giving up.

That’s why, when it comes to learning, it’s nice to see a map of the whole confused, messy journey:

The slick, polished look of the app and its refactored, tidied-up codebase doesn’t tell the real story about how it was created. It skips the hours spent digging into that elusive bug, the time stuck while crafting a particularly tricky piece of logic, and the endless UI tweaks to get it looking just right.

You company’s engineering journal on all the cool things that went into your 1.0? That’s awesome. Your slick and polished app? Amazing. Your talk on best practices for using, I dunno, whatever JavaScript framework is cool these days? Inspirational.

But when I sit down to try my hand at creating something, it’s comforting to have seen that great things aren’t just born that way. Seeing the gaffes and the dead-end experiments that didn’t make it into the final artifact is reassuring: when they happen to you, they feel less like failures, less like monumental wastes of time, and more like a part of the learning process.

And therein lies the rub, the disconnect: we talk up the value of learning from others’ mistakes, and then put in all kinds of effort to scrub clean that which we put out into the world.

Maybe that’s doing us all a disservice. Maybe that’s to be expected in an age where we focus on social media over social learning, but maybe we can do better —and get better— by being a little bit less perfect.