Free to Be Great

When I first joined Etsy, it was my first job attempting to manage a team of people. In previous jobs, I’d been senior to other designers, and even mentored designers to help improve their processes, but this was the first time I would wind up officially responsible for others. And while I was excited, I was simultaneously pretty terrified. What if I failed? What if I found out I was a terrible manager? What if I hated the role and wanted to design full-time again instead? In my first one-on-one with our Creative Director, Randy, I laid it all out there.

I just want you to know that I could be totally wrong for this role. I’m going to try really hard to be great at it, but the truth is I’ve never managed a team before and might wind up being not very good at it.

Without missing a beat, Randy said something I’ll never forget.

That’s okay, don’t worry about it, he said. If you’re bad at it, or hate it, you’ll know it, I’ll know it, we’ll talk about it and figure out what to do from there.

A lot of companies pride themselves on openly failing and iterating on their products. So few allow their people to do so with their careers. With that one conversation, I was suddenly no longer afraid of being fired if this new role wasn’t for me. I could try it out, do my best and have an open and honest dialogue about how it was going. With the fear gone, I was more willing to try out new processes and ideas, and less likely to sweat every single little step and decision. And when something I tried didn’t go the way I expected, I felt comfortable seeking help and guidance right away. I’m not sure I’d still be a manager today if I hadn’t been given the freedom to try and to stumble and to improve.

We can only be the best versions of ourselves when the outcome from an honest effort is experience and iteration.

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