Winging It

Published on by David A. Kennedy

Wing it. That’s what I do. Every day. I figure it out as I go.

This is especially true in my work as a designer. And in my role as a parent. As a significant other too.

I’m finally okay with this. I’ve learned how to fill the space created by the anxiety of “winging it.”

I remember linking to a post by Heydon Pickering about signs you might be a desiger, and thinking, “Oh, that is what I do.” At the time, I thought I might end up going the developer route in my career. I put energy into learning more development paradigms, like a backend programming language and command line best practices. But as JavaScript took hold, I learned that the world of APIs and build processes didn’t excite me as much as the real interface. I began leaning more into the design side, figuring out flows, crafting interfaces and parsing out strategy. No matter which side I worked on though, I felt like an imposter, always missing an important piece of knowledge or skill.

And here I am, more than a decade into the field, focusing on accessibility and people management as a designer. I fill the anxiety of winging it through curiosity. I know I don’t have all the answers, but I look for them through questions.

I worked with a great design leader, and watched him ask many, basic questions every day. If he learned something, he would echo it with enthusiasm out loud in a public space. Like an audible “Oh!” or he’d repeat a phrase someone had said about the thing he learned. It makes learning something basic more normalized. I try to do this too, but it’s a skill. You have open yourself up to feeling vulnerable.

We all wing it every day. As Oliver Burkeman puts it, crossing bridges:

This objection helps clarify what “winging it” really means. Of course pilots and doctors and engineers – people highly skilled at navigating complex bodies of specialist knowledge – aren’t just bumbling randomly through life like idiots. But in another, arguably deeper sense, they’re totally winging it. Like anyone else, they can never grasp the whole of the situation in which they find themselves; and like anyone else, they can never be certain about what’ll happen in the very next moment, let alone a week or a month from now. Like all of us, they’re just crossing bridges as they come to them: they can’t depend in any absolute way on the bodies of knowledge in which they’re trained. Life is always bigger, and more unknowable, than any set of concepts we use to try to make sense of it.


Tagged  Personal