Freelancers are expected to be both specialized and flexible -- there’s no such thing as a monochromatic career anymore. Not only are we supposed to hone our specific talents, but to stay on top of our game and pick up gigs, we need to learn new skills.

Sometimes this whole learning-new-skills thing goes well, and ta-da! you’re a front-end whiz kid now. Other times, you struggle. And struggle. And struggle. Which is weird: you’re smart, and learning new things should be easy and fun!

I’m reminded of something Ira Glass said, which applies to beginners but I think is worth remembering when anyone -- seasoned freelancer or no -- picks up a new skill:

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.”

I failed at my first big design project. It was my sophomore year of college and I volunteered to do layout for a print magazine on software I only had the faintest idea how to use. There were times when I felt like giving up and emailing the Editor-in-Chief to say, “sorry, can’t do it! xoxo larissa” before disappearing off the planet.

But I did it. And it was… okay. And the next time was good, and the one after that even better.


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As horrible as that initial learning experience was from start to finish, I have to give my optimistic college self some credit. In my tender youth, I believed in me. I gave myself a chance. I thought I could take on this project all on my own and figure things out along the way -- and you know what? I failed, but I learned something.

In fact, setting yourself up for confusion and failure is one of the best things you can do while learning a new skill. It’s like how in immersion language classes, even your instructions are given in a language you clearly don’t know. By being confused and likely to fail, you’re forced to solve problems, rather than passively absorb information that’s easily related to you. Writes Annie Murphy Paul:

“The feeling of being confused, of not knowing what’s up, creates a powerful drive to figure it out. We’re motivated to look more deeply, search more vigorously for a solution, and in so doing we see and understand things we would not have, had we simply been handed the answer at the outset.”

If I hadn’t tried to do something that big on my own, I don’t know if I ever would have learned InDesign to the extent I know it now. I was confused, I was set up for failure, and it forced me to pick up skills quickly.

So when you’re learning new skills don’t be afraid of failure. In fact, set yourself up to fail. Encourage it. Feeling confused? That’s probably a good thing.

Larissa Pham is an artist and writer based in Brooklyn, New York. She works at the Freelancers Union.