Sara Wachter-Boettcher

Sara Wachter-Boettcher is a content strategist and writer based in Lancaster, Pennsylvania. Sara is editor in chief at A List Apart magazine and contributes essays and articles to publications such as Contents. When she's not speaking at conferences, writing for her blog, or signing copies of her book Content Everywhere, Sara likes to drink coffee with the same perfectionism and realism she puts into her work.

You can follow her on Twitter @sara_ann_marie.

Published Thoughts

I’m out of ideas.

I’ve been thinking about this post—my last post, my final chance to whip up something fresh before next year’s Pastry Boxers take over—for weeks now. How do I end the year with something suitably Meaningful and Important and Memorable? How do I take these themes I’ve explored all year—themes like empathy and empowerment and letting go of control—and tie them up with a tidy little bow?

Truth is, I can’t. I’m looking back at a year that was strange and lovely and transformative and absolutely exhausting, and I don’t know what it all means, much less what I want to say next.

I don’t think I’m the only one.

I talked with lots of friends and acquaintances this year who wanted to start speaking or writing or working for themselves, but were anxious to take the first step. “Everything I want to talk about, someone has already said—better,” they’d tell me. “Do I really have anything new to add?”

They were out of ideas.

I also spoke with friends who were doing high-profile stuff all year—people who wrote books, keynoted conferences, led massive projects, started products. And guess what? They were all anxious, too. They were worried they’d used up their current schtick, and they weren’t sure where to find a new one.

They were out of ideas.

We all feel this way sometimes—that we’ve spent our intellectual capital, that we have nothing new to add. Even the smartest, most successful, most dynamic people you know. But it’s a lie. We don’t need a new schtick to say something valuable. We just need to be thoughtful and kind and also critical—willing to take a hard look at our work, our community, and our lives.

The ideas will come when they’re ready. In the meantime, I’m taking a break.

Roll up your sleeves and make the thing, perhaps rough and ready and Frankenstein’ish but alive. Show your client/user/stakeholder/team exactly what you mean. Even, and especially, if you’re used to producing strategic documents that describe how things should be made. Know this: as a strategist, you can make and you should make.
—Kate Towsey, “A Content Strategy Clarion Call

I felt myself nodding along at this post from a fellow content strategist the other day, cheering for her dive into the depths of the details, her rejection of hundred-page “recommendations documents,” her inclusion in every prototype.

There’s something beautiful about bringing a content focus into the heart of a design team—about getting content strategists “out of the sidelines and onto the fields” of a project. Tussling with language and labels and tasks and concepts allows us to wrap our arms around a problem, wrestle with it, and solve it. Designers and developers hear new perspectives. The whole project is strengthened, and it’s extremely satisfying.

But I couldn’t help but feel like there’s another half to this story about what makes content strategy powerful—a half we don’t talk nearly enough about in our urge to get agile and ship and productize all the things.

It’s not in what we do on any given project, though. It’s in our opportunity to immerse people from far outside our project teams into this always-changing world of web-making.

The “project” problem

As web professionals—not just content strategists, but designers, developers, IAs, what-have-yous—we tend to work on projects. Whether we’re external agency types or internal web teams or consultants or pretty much anything else, we parcel out our time and energy into tidy chunks: phases, launches, sprints, versions.

When we do, we set up neat borders between our work and the rest of the organization’s day-to-day operations. We think of maintenance and even governance as the proper upkeep of our project’s output: a way to keep the product running smoothly. We assume that the control we have over the website during its redesign is the way it will be controlled forever.

Only the web doesn’t really work that way. There’s always a messy middle between the project and the organization—a silty confluence where the waters of one can’t help but merge with the other. The website has to hook into a billion different backend systems. The customer service team uses the same help content as the website. The departments need to contribute content that meets new formats. Products change, priorities change, people in charge change.

The web is too big, too intertwined with anything and everything organizations do, to be neatly confined to a project scope.

And when everything is online, suddenly everyone is a web worker, too—even, or perhaps especially, all those nonspecialists whose crappy content we’re so busily trying to fix.

Yet we keep on trying.

On making

I started working on the web seriously when I joined an agency in 2007. They didn’t think they were hiring a content strategist, though. They thought they were hiring a web writer—someone to pretty up clients’ crappy old stuff and make it ready for the new (usually already designed and built) website. Someone to type up neat little pages called About Us and Our Approach and the dreaded FAQ. Someone to (elegantly, of course) cram a few keywords into the blurbs the “creative copywriters” had already produced.

It sounds silly now, this way of thinking about web content. Hell, it felt silly then, and it’s why I started pushing for more: more thought going into content, more involvement in the early parts of projects, more emphasis on what we’re trying to say and what our users need.

But you know what I did a lot of then? Making. I made words. I made sitemaps. I made decisions.

It was far from ideal, of course. Our research rarely included users; our design team wasn’t cohesive; our process was less than collaborative. But the making—the getting-in-and-figuring-it-out part—still felt powerful.

At least, it did at first. But every time we’d launch a site filled with some shiny new copy, I knew it was only a matter of time before the friendly features would be replaced by a copy-and-pasted press release announcing news no one cared about, before simple sentences would get run through the corporatese generator, before the pages and pages of third-person, dead-to-the-world dullness would be tacked back up all over the place.

It was only a matter of time before my work withered and wilted.

On documenting

I never intended to make documents for a living. But I felt like I needed to do something to fill this gap between the making and the sustaining.

So I started making deliverables. I wanted to give my clients and colleagues a way to understand and follow along with the choices I’d made. Style guides, content models, templates, tip sheets: endless documents designed to educate and prepare and encourage people to continue using the system I’d carefully planned out for them.

I think a lot of content strategists feel the same: they started making documents as tools to explain their work, and help others understand the implications of the choices they were making with content. Here’s why we are doing this, and here’s how you should keep doing it.

The problem is, this line of thinking still only treats content as an input—the thing that goes on the website, the thing that fills up our CMSes and our pages. And what it took me a long time to realize—to articulate and understand and truly accept—is that content is also an output: the product of an organization’s underlying culture, priorities, assumptions, and beliefs. The systems I was planning for them—and the documents that came out of the process—weren’t doing enough to take that into account.

Whether I was making or documenting, I realized I needed an approach to content that fit the cultures I was working with. And the best way to make something fit a culture is to have it come from that culture.

Getting down and dirty with the design process may give us better inputs for our projects—a real and valuable benefit. But alone, it will never change our organizations’ ongoing output. That takes a different sort of labor—one that’s a lot less about us getting muddy on a playing field, and much more about asking some unlikely others to join the team, too.

Toward a parallel process

The thing is, we do need projects, those defined chunks of time and activity where shit gets done. We can’t sit around eating deli sandwiches in conference rooms all day. We can’t try to solve every problem and design for every platform with everyone in the room all at once. God, we’d all go nuts within a week. Breaking things into stages or sprints or whatever works for your organization is necessary, and so is having a defined team to work on those projects.

So lately I’ve been thinking a lot about how we can better juggle these two needs: the need to work on content, closely and deeply, throughout the duration of a design project, and the need to empower all the people who will make or break your project once it is out there in the wild to make good decisions and stay on track.

I don’t have all the answers to this yet, but I do think the solution starts when we stop thinking of the people who request and produce and update and approve content as outside of “our” web projects and teams, and instead see them as just as critical to collaborate with as designers and developers.

This requires two parallel processes: one that’s all about keeping the project moving, and another that’s all about shifting people and culture. Content strategists, at our best, are the bridge—the people who can navigate both simultaneously, and reconnect them throughout the process.

For me, this has meant taking the questions I used to try to answer in documents, and asking my clients them instead—often using hands-on activities that include people from as many departments and levels as possible:

  • Where isn’t our content matching our mission? Why?
  • What are its strengths?
  • How could this be better organized?
  • What content do our customers/readers need on their journeys?
  • Do we have that content? What’s missing?
  • Where and how should content be surfaced to support that?
  • What’s keeping us from making content available at those times? How can we fix that? What structures would enable that?

I used to think these questions were best left to the experts (a.k.a. me), but I don’t anymore. Because I’m not the one who has to live with these decisions for the long term. The more I guide others as they explore and debate and agree on answers, the more the strategy becomes not mine, but theirs.

It’s not always easy, of course, asking a workshop full of nonspecialists to agree on a core purpose or make a content model or rewrite a page of copy in an hour. This isn’t their expertise, after all—it’s mine.

But their version is often more powerful.

Because when strategy emerges from collaboration, it becomes shared knowledge. It becomes culture. It gives our projects—those projects where we’ve worked so hard to roll up our sleeves and make things—a chance to live on.

I’m all feelings these days. Mushy-smushy, ooey-gooey feelings. I go to a conference and end up at a dinner table with my content strategy colleagues, telling them about the time a particularly dramatic truth-or-dare misstep got me ostracized for the entirety of sixth grade, and how I felt ashamed of the whole thing, still, almost two decades later.

I finish up a staff planning workshop for A List Apart with bear hugs and text messages full of <3s, sappy as all get-out about working with great people.

I try to write about my content strategy work—the often very practical stuff I do to help organizations make their content make sense—and I end up with posts about being vulnerable, about fear, about having a good cry at a conference.

When’d my work life get so emotional?

I didn’t intend for that to happen. I thought I’d keep on writing about content modeling and editorial strategy and mobile. I thought I’d take on substantial posts about rolling up my sleeves and figuring things out. But the more I did that work, the more I wanted to write about the other stuff, too— the barriers I ran into trying to get work implemented, the people problems and political reasons that content is so hard.

And that’s when it started getting squishy. Because the more I explored those things, the more I realized that I couldn’t keep talking about organizations’ messiness unless I was also willing to talk about humans’ messiness.

And this particular human? She’s pretty messy. I forget to listen sometimes. I’m antsy. I’m inconsistent. I’m helpful and supportive—as long as you’re doing the thing I think you ought to. I’m ambitious—so ambitious I sometimes seek out things I don’t even really want.

I’d love not to admit all that, but I have to now. It’s part of the deal I made with myself this year: if I want people to be honest with me, if I want my client relationships to be based on shared values and actual connection, then I have to bring my whole self—in all my not-quite-right glory—to the table.

Being real—desperately, painfully, awkwardly real—used to terrify me, but it gets easier the more I do it. People I love and respect the most have even told me that opening up and talking about their struggles with depression and fears of inadequacy and general not-always-having-their-shit-together has led them to their most satisfying work to date.

That doesn’t mean it’s easy, or that everyone will understand—as my friend Shannon Fisher spoke about at the Dare Conference:

A friend told my husband he thinks my blog is too much. Inappropriate. This friend runs a company and would be an ideal client for the business I started in January of this year after leaving my nine-year teaching career to pursue different dreams. I had to ask myself if our friend is right—am I too much? ... I talked to a friend about losing clients because of my openness. She said, “Shannon, you’ll have the most success being you.”

So will I, I think. So will you.

A few days ago, I had the chance to attend the Dare Conference—a conference about people skills for digital workers. A conference filled with personal stories and intensity and honesty and love. A conference as unexpected as it was necessary.

A conference I won’t soon forget.

My talk was about realizing that, no matter how deep my knowledge is— no matter how good I am at identifying problems for clients and colleagues, no matter what my practical skills are—I can’t actually fix things for other people. My work doesn’t stand alone; it rises and falls with others’ capabilities, with others’ interests in living out the ideas and recommendations and systems and structures I’ve spent so long defining. This topic has been bubbling up quite a few times for me recently—but this time, it felt more raw. It felt like I’d put more of me onstage than ever before. You can watch it in full here (I get started at the 7:00 mark):

Maybe it was the context that made it different, gave me that sense of urgency. At Dare, I heard stories about people struggling with depression, and what that’s meant for their work. People who’ve fought off impostor syndrome, and want to help others do the same. People who were terrified of change in their organizations, but found the courage to embrace it anyway—and are having the career of their lives because of it. Many of these talks were extremely personal. All of them were thoughtful. Several of them made me cry.

Why have a conference about feelings, though? How will a good cry help us as professionals?

These are questions my friend Jonathan Kahn, who organized Dare, got a lot leading up to the event. It’s tough to get bosses to approve budgets for feelings, but after attending Dare, it’s clear that a few more should have.

Because the people we work with are human. They’re messy. And, more often than we want to admit, they’re struggling. They carry that with them, every day, as they sit across from you in meetings and obsess over design decisions and gossip at coffee and analyze research and do all the other tasks that make up our workdays.

You could say those messy feelings aren’t relevant to work, that their struggles are personal problems. But the thing is, our jobs are changing quickly. Keeping up with digital change means we can’t rely on rote job descriptions and checklists anymore. We need to be able to adapt, constantly. And adapting requires taking risks and collaborating with one another.

But taking risks and collaborating don’t happen by themselves. They require openness and vulnerability. And openness and vulnerability? They require trust.

Trust comes when we feel valued, understood, and important. It comes when we feel like we’re appreciated and embraced as whole people. And when we feel stifled, feel like we can’t be ourselves on the job, feel afraid of having emotions? We retreat to what we know. We don’t take risks, that’s for damn sure. We can’t embrace the changes organizations need us to to transform their businesses.

When we’re stuck, our organizations stay stuck, too.

Dare felt like a chance to get unstuck. A chance to admit that our work and our feelings go hand in hand. A chance to help one another start pushing our organizations and clients to more honest, wholehearted places. Places more of us could stand to reach.

So when you have a few minutes, watch these talks. They’re not practical—not in the way that case studies and action plans and technical walkthroughs might be. They’ll make you feel. But then, they’ll make you think. They’ll make you look at your work, and your coworkers, a little differently.

If you’re anything like me, I think they’ll stick with you.

“You need to remember that problem-solving and consulting aren’t the same thing.”

I’d just had a tough conversation about a client project when a mentor of mine said this to me a few months ago. And I knew immediately what she meant. I’d been so caught up in the fact that I saw what this organization was doing wrong—why their website had become a dumping ground, where they needed to change their processes, what they should be focusing on—that I could have sat down and diagrammed a tidy little flow chart right there. And yet, my client wasn’t happy.

Specifically, my client wasn’t happy with me.

Like getting pushed from behind or dumped on prom night, I hadn’t seen this coming. I had the answers, after all. I was solving the Big Problems, problems that others didn’t have the tools to untangle, problems others had struggled with for years.

Only I hadn’t spent enough time listening to make my client feel heard. I hadn’t made them part of the solution. So there my client was, feeling overwhelmed and left behind, while I was patting myself on the back.

It’s difficult to solve complex problems, and I’m proud that I’ve amassed the specialized knowledge to do so. But as hard as it was to get here, I’ve become convinced the next step is much harder: learning to shut my trap long enough to guide people to solve those problems for themselves.

We’ve been talking a lot about ceding control recently—about accepting, finally, the “ebb and flow of things” on the web, as John Allsopp called us to do more than a dozen years ago. This applies to how we design, sure—to the way we deal with varied devices, screens, and capabilities. But I think it applies far beyond as well.

Whether we’re talking about fluctuating screen sizes or flip-flopping executive stakeholders, it’s the same thing: my control is limited. I’m one person, one project, one input. I’m no mastermind.

My perfect model means nothing in an organization that doesn’t care, doesn’t understand it, isn’t ready for it, or can’t implement it. I’m not creating something perfect and finished. I’m participating in something that’s continually evolving, with or without me.

Trying to control things doesn’t make my work more significant, frustrating as that may be. It actually makes it less so.

I’ve written before about how I’ve been trying to stop fixing and start facilitating change, trying to help organizations through the shifts that our work necessitates.

That conversation was a humbling reminder of how difficult that actually is.

Masterminding is a myth, a lie that encourages egos and makes us whine when we don’t get our way. It tells us that we are brilliant, and it’s just those terrible others who are always ruining things. It’s an easy story to tell ourselves, this us-versus-them trope. But it’s not how the real work gets done.

“Stop being so sensitive.”

I wonder how many times someone’s said this sentence to me. If you’re a woman with opinions, you can probably relate. It’s an insidious little phrase so common it’s hard to keep track of how often it comes up.

Last week, I watched as yet another woman was accused of being “too sensitive” and “overreacting.” Her crime? Responding with an eye roll when a man commented on her appearance rather than her presentation or her CSS skills.

I didn’t talk about this particular outburst when it happened, though. I was too busy.

I was visiting my mom.

My mom’s a professor of chemistry at a big state school, but she didn’t start out there. She started out the second of five kids in a poor-ass family outside Munich, the daughter of an abusive artist living a childhood she still struggles to talk about.

She’s been told she’s “too sensitive” her whole life, too—by her dad, of course, and also by a whole parade of people in her 30-year STEM career—people who thought that her small requests, like asking to fix a building lock after multiple break-ins so she felt safe working alone on the weekends, were silly. They weren’t concerned, so her concerns must be irrational.

“Stop being so sensitive.”

The problem with last week’s kerfuffle isn’t that some guy tweeted a compliment about a talented woman. He’s not a villain. He’s just a human being who thought another human being was gorgeous and failed to realize the underlying sexism involved with saying so in that context. When you live in a culture with a lot of underlying sexism, it’s bound to happen. Replying to his comment to let him know it was in poor taste isn’t overreacting, though. It’s simply reacting. That’s how conversation works.

The real problem is the same as my mother’s: the idea that because other people weren’t uncomfortable with the comment, her discomfort was irrational.

“Stop being so sensitive.”

This marginalizes the person who dares to speak up when they’re uncomfortable, and that’s bad enough. But it’s also bigger and more systemic than that. The more we tell people who are different from us that their needs and boundaries aren’t OK—and that they’re abnormal and irrational for having them—the narrower our community’s perception of normality becomes.

And that narrow viewpoint is something we carry everywhere, including right into our work. It leads us to more apps designed by and for the tech elite, more assumptions that everyone has access to the latest devices and endless bandwidth we enjoy, more misguided attempts at workplace “culture” resulting in what amounts to anti-diversity policies—because anyone who’s different just doesn’t “fit in.” More confidence that our individual worldview is the worldview.

Want to design great things for everyone? Want to make websites and products and services that attract their entire potential audience? Want to end up with stronger ideas because they’ve been viewed and vetted through multiple lenses, not just ones that are the same as your own?

Then stop being so insensitive.

Last weekend I packed up my two cats and drove them from our little house with an idyllic backyard in Lancaster, Pennsylvania—a small Colonial city surrounded by Amish country—to a sublet in South Philly, which had, up until literally the moment I arrived, been occupied by two other cats.

After a week of injustices—their stuff boxed up, their furniture taken away, my husband (their favorite) off to a conference in England—this was the last straw. One stayed under the bed for a full 24 hours. The other violently threw himself against a closed window, attempting to will his body through the glass. Both were plainly terrified.

Can you blame them? After all, we humans aren’t so different. Change is scary. And when big changes stack up all at once, we’re likely to go into shock and behave exactly the same: either we publicly freak, or we retreat into hiding.

If you’re the one tasked with getting people on board for big web projects, you’ve probably seen it happen. Midway through implementing the new CMS, so-and-so digs in his heels and demands his process stay exactly the same, refusing to even look at the plans for the new interface. The project lead gives up on managing his 74 internal stakeholders, and now you’re trying to cater to each of their 74 different whims instead. The VP has heard too many conflicting opinions, so she refuses to make any decision at all.

We often roll our eyes at this stuff. We complain about how they “just don’t get it.” We call them irrational, irritating, and difficult.

Perhaps they are. But humans are irrational, irritating, and difficult—all of us, not just our clients and bosses. It’s a lot more useful to let go of the petty annoyances and consider why they’re acting that way. What are they scared of? Have we been pushing our agenda too hard, too fast? Do they feel in the dark and confused?

Do they just need some time to breathe, to look around, to get more comfortable?

If you’re used to the idea of the web changing quickly, then all this endless ego-soothing and placating—this talking around the problem instead of digging in to solve it—might seem silly, like a big fat waste of time. But many of the people we work with haven’t been living and breathing this stuff for years. The changes we propose, even when they seem minor to us, can feel positively monumental to them.

We like to think that our jobs are just designing and building, but they’re not. If we want to do our best work, we have to also bring others along with us, and ease them through the painful adjustments our work necessitates. We have to give them the time and space to get comfortable, to crawl out of their hiding spots on their own terms.

After all, the web won’t stop changing, and change won’t stop being scary. If we’re not going to do something about it, why are we here?

While my friends hawked video rentals and pulled espresso shots, I spent college working at my county’s rape crisis center. For $7.25 an hour, graciously provided by federal work-study funds, I trained volunteers and answered crisis-line calls. I wrote newsletters and set up card tables at local events.

But mostly, I talked to 11-year-olds.

Armed with laminated poster boards and nametags, a colleague and I would walk into a new sixth-grade classroom each week. For an hour at a time, three days in a row, we’d talk about staying safe, about saying no, and about being assertive. About the way boys and girls are often expected to be, and how that sometimes sets everyone up for trouble. About how abusers will sometimes tell you it’s your fault, but it’s not, no matter what.

At the end of each day, we’d collect “anonymous questions”: little paper scraps on which students could write down anything they were afraid to ask out loud. If they wanted, we always said, they could also ask for help and include their names.

In nearly every class in nearly every school, someone would write about abuse he’d experienced, or that of a friend who’d confided in him. They were often aching to tell someone.

We were just the first ones to ask.

Sometimes it took two hours in a cramped back room behind the principal’s office, sometimes ten rushed minutes in a quiet hallway. But each abuse disclosure unfolded in largely the same way: slowly at first, and then all at once. Stories and feelings and sometimes tears gushing forth, engulfing them. Engulfing me.

And then that was it. We’d pack up our role-playing props and poster boards, never to see those kids again. We couldn’t return to their classrooms or contact them at home, much less find out whether they had gotten help or their abusers had been stopped. We simply filled out the requisite forms and handed them off to the school’s administrators, hopeful—yet far from certain—that things would work out.

But I didn’t want a form. I wanted to make things right for those kids. I wanted to take them in my arms and tell them, unequivocally, that they were safe now, and that it would never happen again.

Instead, I left those sessions angry, sad, and drained. I was angry because they deserved better, and even angrier because I knew how hard it would be for them to escape not just the abuse, but feeling that they’d done something wrong, that it was their own damn fault, that they should be ashamed.

I wanted to wash the guilt away for them.

But life doesn’t work that way. Whether you’re a crisis worker or a web worker, it’s all the same. You can’t fix things for the people you’re there to help. You can only get them started.

In hallways and counselors’ offices, I may have loosened the seal of fear and shame that was bottling up a child’s voice. Yet she was the one who had to speak, and keep speaking, until her life changed. She had to regain her own sense of power, not be saved by mine.

My head knew this, but my heart wasn’t convinced. I’d still spend every drive back to the office the same way: shaking with frustration and wishing I could swoop in to make it all OK.

It wasn’t until much later, years into a consulting career, that I understood how foolish this longing really was. Promising solutions to people in need, even people in crisis, may be immediately comforting, but it’s ultimately dishonest.

At my best, I can ask the questions they’ve been aching to answer. I can light a path between the experience they know and the experience that could be. I can give them the space to find their way, and the confidence that their way is worth finding. But their problems will never be mine to fix.

Soothing CEOs with bon mots and buzzwords or tossing technology around like confetti won’t help. Real change comes from within. There’s no outsourcing it, no papering it over, no substituting someone else’s efforts for internal ones.

The world doesn’t need more solutioneers. It needs more advocates.

I’ve been lucky enough to get a lot of feedback recently: book reviews, conference talk evaluations, post-workshop surveys. Reams of paper and multi-column spreadsheets and emails and blog posts all dedicated to evaluating little ol’ me.

I don’t always feel lucky, though. More often than not, reading a review of my own work (or, worse, dozens of them all at once) feels excruciating, overwhelming, and exhausting—even if it’s positive. It always seems to find the spots where I have the least armor and jab itself right in.

But I am lucky. I’m lucky people bothered to take the time to tell me how I did. I’m lucky people cared enough about what I said to tell me the ways in which I can do better next time.

Most of the notes I’ve gotten have been positive, but of course I have plenty of things to work on: Slow down. Get more specific. Make more obvious ties between the little things and the larger narrative. Calm down. Slow down.

No, really, slow down.

I’m working on those things, of course. (I think I’m speaking about 25 percent slower than I used to—which is only 25 percent faster than I ought to be.) But even more than that, I’m working on how I relate to the feedback itself.

For a long time, these waves of feedback would bowl me over. I’d get knocked into a state of panic, obsessing over all the things I could have done better. I’d end up tumbling, reeling, scrambling to regain my footing. This felt crummy, sure. But the real problem was that it also left me unable to do anything with the information—because getting back up off the ground had already sapped all my energy.

It’s hard to take change to heart while you’re coughing up saltwater.

These days I’m trying to let the wave wash over me without it kicking my legs out from under me. Either way I’ll end up getting wet—immersed in the criticism, soaked in my own imperfection. But if I want to get better, I can’t afford to get swallowed by it anymore.

It’s not just about me, though. It’s about our entire industry, as my friend Jonathan Kahn pointed out recently:

If we’re going to change culture, we need to give and receive feedback more, and we need to do it with kindness and respect. Which is HARD.

If you agree that culture change is critical to the web—that businesses need to adapt to constant change, that organizations need to get back to being human, and that becoming flexible and iterative is the only way to keep up—then embracing and employing feedback isn’t just a means to being better liked. It’s actually the foundation of a better web.

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.

People ask me all the time how they can get started in content strategy: How do I convince my boss to let me do more? How do I go beyond being a writer or a content manager? How do I wrap my head around content as systems and sites get massive and messy?

Usually I end up tossing something out about asking tough questions and poking your nose where you don’t belong until people start incorporating you in their projects.

That’s not a lie, but it is a bit of a cop-out. Because I believe the real answer starts not in what you do, but in how you think.

The people who are best at strategic work—actually, scratch that, the people who are the best at practically anything —share a common trait: the ability to hold big ideas and minute details together in their heads at the same time—and to constantly, naturally, be vetting one against the other.

They can come up with a concept, then immediately find its weaknesses and figure out its feasibility. They can look at a bevy of tiny details and see which of them are actually important to the big picture—and which aren’t worth sweating. They understand that minutia like microcopy and QA matter, but they don’t get stuck on them so long the rest of the project suffers. They’ll dream up a cool way to personalize an experience, then immediately ask whether they have the data and logic to actually deliver it.

I’ve seen too many projects fail because the people with the “big ideas” didn’t see it as their job to care about the small stuff, too. And, just as detrimental, I’ve seen too many people waste their time and skill sets by getting so hung up on formatting a laundry list of content recommendations that they can’t see the bigger themes and opportunities.

Vision is lovely, but vision alone doesn’t ship. It’s the people who can carry vision through—and not just by handing off a plan or drawing a diagram, but by actually working through the challenges of execution—who are most valuable.

And boy could the world sure use more of them.


2012 was a weird year. I wrote a book, moved 2,400 miles, started editing a magazine, and gave talks on four continents. I even pet a cheetah.

But it was also the first year in memory where I didn’t read novels.

Oh, I read all right. I downed blog posts and skimmed technical titles. Scoured web-professional articles and tried to keep up with the news. But for most of the year, the closest I got to a work of fiction was hurrying through a short story at the airport.

Sure, I’d started Ada or Ardor—a sprawling Nabokov tome that reads like a Tolstoy family drama, if old Leo were high on modernity, absurdity, and possibly mescaline—in January. And I was falling in love with it, too, in all its illicit eroticism and decadent allusion. Yet I put it down a third of the way through and never managed to pick it back up.

This isn’t like me at all.

At first, I thought the problem was a lack of work-life balance—that I was spending too much time slaving over projects and paydays, and not enough giving in to curiosity and culture. But the problem wasn’t just that I was working too much (though I probably was). It was that I’d cut off my nose to spite my face: In order to make more time for work, I was removing the very things that allowed me to get any good at my work in the first place.

You see, the truth about the web is that there’s no inherent there there. The only substance it has is the substance we give it—which means that if we’re not substantial people—people who’ve read far and wide, thought long and hard, and discovered what it is that matters—then the web work we’re capable of will always be shallow.

Don’t get me wrong. I love my work. I love thinking about users, helping organizations get more realistic about publishing, and making content memorable. I love my clients. I love writing about and working on the web. Most of all, I love the array of super-smart people I’ve had the chance to meet, work with, and learn from along the way. But if we don’t explore the rest of the world—if we don’t get outside our work and wander into whatever weird corners we fancy—we’ll never be able to give our work life. We’ll have a slew of “best practices,” but nothing worth practicing.

It’s not just about reading novels, of course. It’s about living fully—about experiencing the world in all its complexity and exposing yourself to ideas that are foreign and challenging. It’s about getting constant practice at thinking critically and connecting disparate concepts. It’s about building interesting things because you’re an interesting person.

So this year, I’m not giving all my attention to the endless novelty of web work. I’m making space for a Nabokov novel.