You’ve probably heard about the importance of empathy in design and communication work—of understanding others’ emotions and considering their feelings when we make things for them to use. Corey Vilhauer has called it “content strategy’s hidden deliverable.” Kate Kiefer Lee says it’s central to MailChimp’s content. Whitney Hess believes it’s the foundation of an “environment that encourages collaboration, iteration, and risk.”

But empathy isn’t easy. As much as I want to have it, as much as I believe in it, I fall down on the job a lot. I dole out advice better than I listen. I get frustrated with people who just can’t figure things out. I’m quick to be an editor when I ought to simply be a friend.

I think I might have found the real problem, though. We can’t begin being empathetic when another person arrives. We have to already have made a space in our lives where empathy can thrive. And that means being open—truly open—to feeling emotions we may not want to feel. It means allowing another’s experiences to gut us. It means ceding control.

Empathy begins with vulnerability. And being vulnerable, especially in our work, is fucking terrifying.


I’ve spent most of my life putting up one front or another: against middle-school taunts, against familial drama, against injustices both petty and profound. I suppose we all have. How else would we get through adolescence, through job rejections, through breakups and bad news and disappointments of all sorts?

Fronting isn’t bad; it’s human. It’s a shield—a way to cope, to keep others at a safe distance, to tell them the story we want them to see. But it’s also what’s keeping us from greatness, as Karen McGrane wrote last month in a column for A List Apart:

I’m comfortable when I can tell myself I’m in control, when I can attend to all the small details and various checklists that add up to “doing a good job.” I had to be forced into a place where I simply did not give a fuck in order to find out what I was really capable of.

Greatness, in other words, demands rawness.

I’ve probably read that piece a dozen times by now (and only two of those were in my official capacity as editor). I keep returning to it because I’ve never before had so many good things happening at once, and yet simultaneously felt so far from great.

This might surprise you if you know what I’ve been doing recently: taking over A List Apart, speaking at conferences, publishing a book. I am, as they say, doing well. Yet that book nearly did me in—and not because of the writing, either. I was simply scared of being exposed.

I was terrified that the things I’d been working on—mostly alone, mostly in a little agency in Arizona that was far from perfect and that didn’t really reflect what I wanted to be doing—were going to get called out as minuscule and silly. That I didn’t deserve to be doing this. That I’d let people down.

I did it anyway. I felt nauseous the whole time.

My fears were unfounded, of course. I’ve received inspiring emails from strangers. I’ve had mostly good reviews. I hear it might even make money someday.

I should feel relieved. I should feel ecstatic. But vulnerability doesn’t work that way. I still feel this intense desire to hide, to deflect, to cover back up all those parts I exposed to the world.

I’ve distanced myself from past projects; I’ve avoided pushing for the sort of work I really want; I’ve glossed over details to avoid admitting how little I actually know. I’ve worked hard, terribly hard, to make my checklist add up to a good job.

But I am not great. Not yet.

Professionally vulnerable

There’s a safety in creating distance—in carefully managing perceptions and avoiding the things that make you feel unprepared and unworthy. It’s easier to get by when you have a buffer.

But that distance not only keeps you from greatness; it also numbs you. It protects you from your own emotions, sure. But it also makes it impossible to feel anyone else’s.

I can’t afford to be numb. I have users to help. I have problems to solve. I have got to get more comfortable with being uncomfortable.

Empathy starts with vulnerability. And I’m still working on it.