Design & Vulnerability

Yesterday I spent the day trying and failing to solve a product design problem. I’ve been working with Dan Mall on SuperBooked, and my latest task involves taking a complicated flow and presenting it in a way that is mobile-first, responsive, accessible, inclusive, intuitive, and welcoming (this is the problem and joy of working for a person who knows what makes a design great: there are no shortcuts).

Everything we do for SuperBooked needs to ultimately forward our goal of helping people find work from people they trust. As someone who has done freelance on and off for over 10 years (sometimes successfully and sometimes failing utterly), this is an issue close to my heart; I care deeply about solving this problem in the best way possible.

So after having my ass glued to the couch for about 6 hours of trying to design a solution and not quite getting there, I was in vulnerability hell. I made the mistake of scanning Dribbble for “inspiration”; studying beautiful finished products created by my talented peers, and comparing these shots to my messy sketches and imperfect wireframes. This is the design equivalent of scrolling a supermodel’s Instagram feed after you just blew your diet and ate a big fat cheeseburger.

After huffing and puffing and pacing for some time, I called in help from my life-and-work co-captain Andrew Couldwell, who is pretty much a varsity product designer. If designing products were a sport, he’d be the star player who never misses a goal and takes the team to the championships every year. When I compare his work to mine I feel like this:

So needless to say his advice is invaluable to me, but I have to be mindful to overcome comparison and shame when I hear his input on my work. Yesterday, I failed.

He listened thoughtfully as I described the problem at hand, and when I was finished he innocently pointed out that my solution wouldn’t account for the complex filtering needed on a feed of posts. I roared back, “I’m not even THINKING about that now, I just want to get this feed to appear in a way that makes sense and I CAN NOT DO IT, DAMMIT.” He wisely suggested that I end my self-imposed ass-glued-to-couch status and that we meet some friends for a drink.

After drinks on the walk home, I just couldn’t let it go. “I wonder if I’m not any good at this any more. I feel like such an imposter. Maybe I should just be designing WordPress themes or doing something that doesn’t make me feel this inept.” And he replied with something that’s stayed with me all day:

“It’s actually a good thing that you struggle like this — that you feel incapable, and want to quit. It means you are passionate about what you are doing, and want to do it right. It means you are GROWING. So don’t give up; every good designer feels this way sometimes.”

I’ve had plenty of gigs where vulnerability did not come into play. Where I confidently sailed through the day to day, bored but smug about my own abilities. While these periods offered some respite from the queasiness of imposter syndrome, looking back they are plateaus in the chart of my growth as a designer. Sometimes I think it would be preferable to live on that plateau, set up camp in a comfortable place of “this is good enough” and carry on designing blogs and email templates and whatever straightforward projects come my way. And who knows, maybe someday I will.

Ah, but then I would miss that high that comes with solving the hard problems. When I land on a solution that works — when after days of wrestling with buttons and forms and typography, I nail it — I feel like I transcend my insecure, flailing self and become Wonder Woman.

One of my favorite writers, Heather Havrilesky, has an advice column in which she gives life advice to (usually young, female) readers. She once described the feeling she gets answering people’s questions in her column:

“…when you ask me this very simple question, I feel like a mathematical genius or a historian whose thoughts separate into layers and then keep expanding to infinity, so that I don’t know where to start because there are just so many possibilities, all of them rich and exciting.”

This comes back to me repeatedly when I try to describe the way I feel after solving a hard design problem. I feel like a genius, and full of possibility — like I have a place in the world and know how I’m meant to shape it. (This is also the way I feel when I write, give talks, and mentor, but those things bring up so much vulnerability and discomfort that I need to call on a really really deep well of courage to do them. But that’s for another post).

Some people might read this and say “come on lady, you are designing web forms, not fighting crime.” But designing for products that matter to me makes me feel simultaneously afraid and inept and thrilled and alive — which, I’m pretty sure, means I should keep doing it.

This morning, this tweet showed up in my feed, and I felt (as I often do) like Jeffrey was some kind of special career angel, speaking directly to me:

Jeffrey Zeldman knows what I’m talking about

Creation leaves us exposed. Taking risks, solving problems, sharing ideas, making things you care about: this is scary work. So if you also feel uncomfortable and laid bare in your work, you are not alone. It’s a good sign; that tension means you are on the right track. It’s what doing the work you are supposed to do feels like. These are your growing pains. Be humbled by them, but stand tall too.

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