Photo by John Morrison

Your friend on the Internet, Jeffrey Zeldman

A series of interesting conversations with interesting people.

Jeffrey Zeldman is every web designer’s friend, whether they know him personally or not. He has spent the last two decades pioneering web standards all while educating, collaborating, and nurturing an inclusive community on- and offline for web designers. We caught up with Jeffrey to chat about how a mailing list curated for web designers two decades ago turned into several successful businesses, how he finds time to be creative away from work, and what he’s been cooking lately with his daughter.

You are a web design entrepreneur extraordinaire, podcaster, writer and speaker. If there is such a thing, walk us through what a typical day looks like for you.

Every day’s different. Here’s how a recent one went:

Walked my daughter to her summer art class, then strolled down to my studio, a few blocks north of the Flatiron Building. The ability to walk everywhere is one of the great things about living in New York.

Met with Jason Santa Maria and Katel LeDu to discuss our next A Book Apart books.

Made progress on our main current design project, with project manager Robert Jolly consolidating the client’s feedback into a succinct, reasonable to-do list, and lead designer Roland Dubois jumping on it.

Met with lead developer Noël Jackson to compare notes on our second meeting with a potential client, plan the pattern library we’re creating for an existing client, and discuss a new team member who’ll assist Noël on both projects.

Wrote to a new player who just joined the potential client’s team, thanking him for meeting with us, and responding to some of the points he’d raised in the meeting. When a new key player joins a project you’re pitching, it’s important to connect with them right away, lest the project slip out of your grasp.

Had lunch with a former client who’s currently the president of a nonprofit that designs a popular online gaming platform that helps kids learn to read. We caught up on each other’s lives a bit, then discussed a web and marketing problem she’s dealing with, and how she might approach it.

Picked up my daughter from summer art class — there was some hilarity with a stuck elevator — and took her to a local spot for vegetarian udon with tofu.

Tried to track down the substantial damage deposit my former studio landlord owes me. But all I found in my mailbox, besides bills, was a Jury Duty summons.

Wrote a recommendation for a former administrative assistant at School of Visual Arts (where I teach one night a week), who’s now trying to get a graphic design job. The recommendation was forms-based: the kind of thing HR departments love, with all the charm of an IRS Schedule C. Assign a numerical grade to the candidate for each of 30 questions. Write three ways the candidate could improve. Write three things that are great about the candidate. How do creative people even get hired out of such totally non-creative processes? It reminds me of the problems we face when pitching an account via a formulaic RFP. Which reminds me of an article I want to write for A List Apart.

Recorded The Big Web Show № 161: Cultivating a Creative Culture with Justin Dauer. Great conversation about fostering a creative work environment that works. Also accepted an article by Justin and added it to A List Apart Sidebar.

Made portobello steaks and sautéed vegetables with cilantro and sweet Thai basil sauce for dinner. My daughter helped me cook.

You founded A List Apart, an oasis for web designers that focuses on web standards and best practices, in 1998. What sparked the idea and how did you get it off the ground?

In 1998, I was passionate about web content, passionate about design, and passionate about code — especially the possibilities of HTML and CSS, if we could persuade browser makers to support those specifications accurately and completely. In my mind at the time, HTML was the cockroach that would survive a nuclear winter — a simple but very durable format for humanity’s greatest ideas (and our dumbest ideas too, of course) that had the potential to last for generations. At the time, there were newsletters and websites about web design, but they were divorced from front-end code. And there were newsletters and websites about code, but they weren’t interested in design, and they weren’t accessibility-and-standards-focused. And there were no publications whatsoever about web content: what it means, who it’s for, who pays for it, and so on.

Via Awwwards

I created a publication that focused on all three legs of the web experience — design, code, and content — because the web needed a publication like that, and nobody else had gotten around to creating one. I was very influenced at the time by the punk DIY (Do It Yourself) ethic and by fanzines. A List Apart was a reflection of that — if you don’t like the magazines that are out there, create your own! And its original design also reflected that aesthetic.

In 1997, an internet friend (Brian Platz) and I had started a mailing list to address those same concerns. I named it “A List Apart.” Within a few weeks, we had 16,000 subscribers. Transitioning to a website the next year was easy: in our newsletter, we told our subscribers about the new site, and they visited. I wrote the initial articles, along with my friends who were Internet content pioneers, including Lance Arthur, Heather Champ, the late Leslie Harpold, Jeffrey Veen, and Steve Champeon. In the beginning, Glenn Davis hosted our site for free on his Project Cool server. Before we created a CMS, I hand-coded every page. Soon Nick Finck took over the HTML production as a volunteer. In the early 2000s, we got our first proofreader (Erin Kissane), a brilliant writer whom I almost immediately promoted to editor-in-chief.

We’ve been publishing for 20 years, and I hope to keep going forever.

Since A List Apart, you’ve also co-founded A Book Apart (a series of brief books for people who make websites), An Event Apart (a web design conference held in six to eight cities throughout the year), the podcast The Big Web Show, and have written one of the most impactful books in the industry, Designing with Web Standards. You clearly have a passion for educating the world about web design. Where does that passion come from, how do you sustain it, and what kind of impact do you hope to have with your work?

I may be a teacher by instinct. When I was seven, my dad taught me the facts of life, and I ran to a stoop to teach kids twice my age about it — starting with the kids in a large Catholic family across the street, who thought “the stork” brought human babies to earth. I still remember the look in Johnny H — — — — — — ’s eyes when I explained about the vagina and penis. But I digress.

As a young adult, I had an alcohol problem, and I was two years into recovery when I began designing websites. My 12-step program had taught me that you only keep sobriety by giving it away (helping others), and I figured the same principle applied to web design.

I loved web design. I loved the power the web gave the whole world to express itself and share. The barrier to entry was low. It would have felt selfish not to share. I was so turned on by what I was learning as I discovered the power of web design. I wanted to turn the whole world on to it. To help everyone discover their passion and publish it for all the world to share. That’s still what gets me out of bed in the morning — the opportunity to learn and share.

What is it like to write about an industry that is continuously developing? Have you ever finished a book that feels outdated before it’s even published?

My first book, Taking Your Talent to the Web, was about making the journey from print art director to web communication designer. In 1999, when I began writing the book for New Riders/Peachpit, the web was exploding, and there weren’t enough skilled web designers to go around. A Dallas entrepreneur, Steve Crozier, saw the need and launched a business he called Populi that would train print art directors in web design and pair them with a job when they graduated. It was very much the predecessor of all the code camps we have now. Steve asked me and another designer to create the curriculum for the program (which we did), and he hired a courseware developer to convert what we were writing into a course. When New Riders asked me to write a book on the same subject, Steve graciously consented to let me use a lot of the same material I had developed for his Populi program.

I was nearly finished writing the book when the “dot com bust” happened. Suddenly, all those hip Internet companies weren’t hip any more. Razorfish and Scient and all those high-powered first-generation Internet startups came crashing down. Nobody was hiring. Everybody was firing.

I knew if we released the book in that environment, it would be sucked into a black hole. But the publisher was beholden to several major bookstore chains — remember bookstores? — and we had no choice but to publish. It was good book, people tell me, but the timing could not have been worse. That it sold 10,000 copies is a miracle. There was no second edition.

Although the book was outdated upon publication due to the chaotic job market that greeted its release, if we could have waited two years and then published the same book, it would have been ahead of its time.

Via A Book Apart

What have been some of the most memorable and significant moments and connections to have come out of An Event Apart?

Ethan Marcotte introducing responsive web design on our stage is certainly in the top five. Media Queries were a new thing in CSS, and they caught the attention of several very smart web designers. On our stage that day, Andy Clarke mentioned how CSS Media Queries might be used to change a layout to fit different viewports. Next, coder (and An Event Apart co-founder) Eric Meyer and designer Dan Cederholm made the same point in their presentations! And then Ethan came out and showed us video footage of a building that reshaped itself to fit the needs and activities of its occupants. This new style of building was called “responsive architecture,” he told us … and then proceeded to explain how responsive web design could do exactly the same thing. It was amazing. Several very bright people came close to articulating how design would have to change in our new world where the desktop was no longer the last word in browsing environments. But Ethan nailed it.

What led you to web design in the first place? What did the road look like to getting there, and what was it about web design that resonated so deeply with you?

I spent several years in music and failed. Wrote three novels and failed to find a publisher. Wrote for The Washington Post and got fired. I had talent but could not find the right medium for it. Perhaps because it did not exist. The moment I got my first web project, I knew this was it. It was what I was made for. What I had waited for. I wanted to share it with everyone, and I needed to help protect it from the forces that ruin every new medium.

Do you still find time to be creative for creativity’s sake?

Yes. I do photography, especially architectural and street photography (although not well); I still draw (although not well); I still play and compose music a little … and listen to music a lot. I write mainly for the sake of expressing myself — most of what I write these days I don’t publish, just share it with a few friends. I make up songs and games with my daughter, who’s a super-talented young artist, and make time every day to do something that’s creative for its own sake.

If you don’t do that — if you only do creative things for a paycheck — you can lose your love of what you do. Having a creative playground of one sort or another is important for every designer and creative person. As important as exercise, nutrition, and rest. Indeed, it is very similar to those three things in what it does for you.

Via lynda.com

What are your go-to places — sites, apps, people, etc — for finding new stories to read and watch in Pocket?

I scour Pocket’s Recommendations every chance I get! And I’ve set up several IFTTT Applets that add content to My List. For instance, if an article in a New York Times section I follow gets emailed more than a certain number of times, there’s an Applet that adds it to my list in Pocket. Or if I favorite, oops, I mean, if I like a tweet in my main Twitter feed, there’s an Applet that adds the first URL shared in that tweet to my list in Pocket. Still another IFTTT Applet saves NASA’s photo of the day to my Pocket list. And another adds everything I add to Pocket to my Reading List in Safari (because Lots of Copies Keeps Things Safe).

I keep up with design via CSS Layout News, HackingUI, Smashing Magazine, and of course A List Apart. I also read all the Rosenfeld Media books, and of course I read all the A Book Apart books several times before and after they come out.

I read the main news in The New York Times, The Washington Post, and The Guardian every day (and I subscribe to those three publications), paying special attention to U.S. politics, international news, and the opinion sections. Likewise, I subscribe to The New Yorker and find great material on politics and the arts there.

Propublica is another treasured news source, particularly for its long-form investigative articles. I also follow selected columnists (especially in The Times), and about 100 journalists on Twitter, who share what they’re reading or what they’ve just written.

On Medium I subscribe to Signal vs. Noise, ThinkProgress, Postlight, and a few dozen others (although the three I’ve mentioned are by far the most consistent). Lots of people and companies start publications but few keep them going. (I know the feeling.)

What have you been finding interesting lately / what have you been saving and recommending about recently?

Look, if you’d asked me two years ago, I’d have shared a board of wide-ranging interests, from design to film, from music to literature, from parenting to yoga and bodybuilding, from photography to travel, and on and on ad infinitum. But since November 8th of last year, I’ve been mesmerized by the hypnotic glare of what feels like our democracy melting down. It’s a terrifying time. And I can’t make sense of it alone. So nearly everything I read (and thus, nearly everything I save to Pocket) is about the Trump presidency. And things are spinning out of control so quickly, that if I were to share my five top articles from this week, they’d be old, forgotten news by the time someone reads this interview.

That said, some of my recent picks include:

“In the 1940s, comic books were often feminist, diverse, and bold. Then the reactionary Comics Code Authority changed the trajectory of comic book culture for good.”

The author of The Magicians trilogy reviews Brian Merchant’s book about the design and meaning of the iPhone.

“Every year, the internet gets a little less fair. The corporations that run it get a little bigger, their power grows more concentrated, and a bit of their idealism gives way to ruthless pragmatism.”

If you had the chance to escape and read all of your current Pocket saves where would you go to do it?

A crow’s foot bathtub in a room overlooking the ocean. I’d happily settle for a crow’s foot bathtub in the Edgewater Hotel, overlooking Seattle’s Puget Sound. My iPhone 7’s splashproof. Sounds like heaven!

(I can’t use the tub in my apartment, because one of my cats is convinced it’s a litter box. Hence my deep appreciation for squeaky-clean hotel rooms with working plumbing.)

Alternate escape: my iPad and a near-empty Quiet Car compartment on Amtrak Acela Express. Don’t care if I’m heading north to Boston or south to Washington, DC, as long as the car’s cool and quiet.

Who would you want to see us interview next?

Molly Cantrell-Craig — Visionary entrepreneur, bestselling author, founder of a nonprofit (Women With Drive Foundation) that helps connect dispossessed people, single parents, etc. with cars that enable them to get to jobs and support their families! A very inspiring human being.

Kate O’Neill — Author, Pixels and Place: Digital Strategy, UX, and Placemaking — hyper articulate author, UX person, former Nashville songwriter (!)

Jen Simmons — Designer advocate at Mozilla, host of award-winning The Web Ahead podcast.

Find more of what Jeffrey is reading and finding interesting here.