Last Thursday’s panel covered a lot of ground regarding the mindset necessary to have a successful career in UX. That said, we didn’t cover all the points that came up during the discussion. There was one in particular that I thought worthwhile, so I’m tackling it here.

The point is the following: Some of the ideas we discussed — e.g., having the agency necessary to move on from a job that doesn’t align with your values — require self-confidence. This doesn’t come naturally to a lot of people, especially someone who may be starting out in their career. Or another way to put it, “that’s easy for you to say, given the stage you’re at in your career. But it’s not so easy for folks like us, who are just getting started.”

It’s an excellent point. It’s natural to feel uncertain when you start a new endeavor.

How do you build up the self-confidence necessary to make bold career decisions? The only way I’ve found to break through is to stick with it through the uncertain phases. There’s a paradox here: sticking with it requires some degree of certainty, but certainty only develops if you stick with it long enough. You must give yourself enough leeway at first to enable you to push through.

In the mid-1990s, I got into rollerblading. Eventually, I was quite good at it; I could do all sorts of tricks and even joined a roller-hockey league. But I still remember when I was first learning to rollerblade. My movements were awkward and jerky. I’d fall all the time​, and injured myself on several occasions. I was often hesitant and scared. At first, each fall made me more uncertain. “Aw crap,” I’d think, “why am I doing this?”

Why indeed. We’re taught that we should do things we enjoy, not things that are painful (or have uncertain returns.) Often, when you’re learning to do something hard, you can feel more frustration than enjoyment. You fall often, you hurt yourself – or at best, make a fool of yourself. (That is, you hurt your ego.) This is a hard period to endure​ since you’re disincentivized to keep at it.

Over time — if you stick with it — the hurt/pleasure ratio inverts. A point comes when you’re enjoying yourself more than you’re hurting. From then on, you’re more willing to put up with the pain. (Or, in the case of rollerblading, you learn how to fall without injuring yourself. That was a major breakthrough for me!) Because of this ratio inversion, you’re doing the activity more often — and with greater gusto. In other words, you’re practicing more. And so, a virtuous cycle ensues: The more you practice, the better you become at it; the better you become at it, the more you enjoy it; the more you enjoy it, the more you practice. And on it goes.

With this virtuous cycle comes self-confidence. You’re less tentative in your choices and more willing to try new things. You stop thinking about your next motion​ and just do it. Eventually, you see yourself as a “rollerblader” (or “designer”) — it becomes part of your identity.

The key here is that this takes time and patience. It’s not something you can learn about in school or books. It can’t be taught.

That said, it can be modeled.

One of the reasons why I stuck with the pain was that I knew an older guy — let’s call him Steve — who was really good at rollerblading. Steve would skate around wearing a Walkman and bouncing fluidly along to whatever song he was listening to. He’d occasionally spin around on his axis, ostensibly in response to some flourish in the music. He’d do this with perfect, thoughtless control. I could tell he was in a state of flow, and it looked utterly delightful.

Steve was a model for the sort of skating I wanted to do. I knew it was possible because, well, there he was! When I became a little better — that is, I didn’t fall as much — I’d try to emulate some of the moves I saw him do. Whenever I’d tumble, I’d consciously try to emulate Steve. How would he handle this?

The traditional way of learning design — that is, before our more formalized educational system emerged — was by apprenticing to a master. Apprentices would join an established studio and help out. Initially,​ they’d help with menial tasks. They’d endure humiliating tumbles, as all of us do when learning something new. They’d be uncertain and clumsy. Over time, they’d get better at it. And the better they got, the better they’d become. All the while, they’d have the master modeling the behavior that made someone “good” at it.

I think about this master-apprentice framework often. I’ve learned — and keep learning — from masters in my discipline. This requires a balance of humility and confidence: “I’m not very good at it yet, but I know I can do better because somebody else is. And it looks like they’re having fun.” It also requires persistence: the ability to stick with it over time, despite the setbacks and uncertainty — to the point where the hurt/pleasure ratio flips.