Describe your path to becoming a designer and web developer.
First, I failed at a lot of different things. When I was a kid, I really liked music, especially rock music. I wanted to be a musician and make records—I had a whole fantasy life, like many kids do.
I loved drawing too. My dad is an engineer, but he was also a part-time painter and belonged to an art club that held exhibitions. He was constantly making mosaics and other stuff and gave me a lot of art books. There were nudes in the art books, so at first I was excited—inappropriately excited by the nudes. (all laughing) Then I discovered William Rimmer, an artist and anatomy teacher from the early 1800s. He was obsessive as an artist. Let’s say he was drawing a forearm to show what the foreshortening would look like. He would begin drawing the arm, but couldn’t help himself; he would draw the entire body, turn it into an angel, and draw it wrestling another angel until the whole blackboard was covered and all the students had left the classroom. He died in poverty, but he made a book that was full of figures in action and drawings of heads showing different ethnicities. It was fascinating to me and made me want to draw.
I loved comics and read and collected Spiderman and others, so I created my own comic book character named Rick Purvis, who was a spy. Every time I created a new comic book about him, I could draw better because progress comes from repetition and trying things—the more you show up and try something, the better you get. To justify why Rick Purvis’ character looked different each time, I made him have plastic surgery to escape his enemies at the beginning of each issue.
From a young age, I wanted to be a musician, an artist, and a cartoonist, but as I grew, I also began to love writing. I got a full scholarship to the University of Virginia and earned my MFA in fiction writing. I tried to get my work published and had written three novels when I met a real author in New York who agreed to share my work with an editor. I was 22 and told everybody I knew that I was getting published, but instead, my manuscript was returned unopened, and I went into a decline.
After that, I was a journalist for a short period of time. Spontaneously, I had taken photos of this place called Shoal’s Coffee Shop in Washington DC. It had really quaint, weird, kitschy knickknacks everywhere and the guy who ran it, Evan Shoal, was pretty conservative, but constantly fed the homeless. I thought it was an interesting character study, so I took all these pictures and tried to bring the story to the City Paper for Washington and Baltimore, but the editors weren’t interested. Then the guy died the next day—he just dropped dead. The paper called me up and asked, “Do you still have that story? Can you just add that he died and we’ll make it an obituary?” So this man’s death jumpstarted my journalism career. I became a columnist, covering the DC go-go and hardcore music scenes. The Washington Post noticed my work and hired me. I reported to Richard Harrington on The Style Section for about two years. Then one day they fired me and I never knew why.
In my mid-twenties, I toured with a post-punk, techno-surf band called The Insect Surfers. The band had been started by a bunch of high school kids who made albums, went out on the road, and became popular regionally. Most of the members quit to go to college, so I joined as a replacement member. Then I decided I didn’t want to be on the road forever, so I ended up in advertising. I worked in advertising for ten years and a girlfriend brought me to New York because she wanted to go to School of Visual Arts. We broke up pretty soon after moving here. She’s a really talented computer artist and teaches at RISD—this is turning into a really long story.
No, it’s good. Keep going.
I was in advertising and saw a lot of politics, which I hated and sucked at. I worked with some really, really talented people and learned about art direction, writing, and branding. I learned that everything comes out of the product and just being clever isn’t good enough. You want to move people; you want to amuse them, entertain them, and make them think. Writing billboards and coming up with quick visuals was good training for the web because you have to communicate something instantly.
So, the web—it was 1995 and I was in advertising and working at Grey Entertainment. I’d gone there thinking, “If I can make a cool commercial for a dishwashing liquid, then I’ll make an amazing video for a rock band or a movie,” but it turned out that I was mostly making posters with stars’ heads and the name of the movie.
Then Warner Bros. came to us because they were going to do a Batman movie. At the time, there were 3 million users on the web and we were using Netscape 1.0 or Mosaic. Don Buckley, the marketing director for Warner Bros. in New York, was really smart and asked if we could make a website for the movie. Our agency president lied and said, “Yes, of course.” Then he came to Steve McCarron, Alec Pollak, and me and said, “Boys, can you make a website?” We also lied and said, “Sure.”
I had only experienced AOL and this was before your time, but AOL was pretty dumbed down compared to the Internet; it was a cute, easy to understand interface. The first time I looked at the web, I said, “Well, this won’t succeed.” AOL was so much better—they had avatars and everything. The web looked horrible. Think about HTML websites in Netscape 1.0—it was very grim.
Steve, Alec, and I didn’t know what not to do, so we made a visually compelling website with good copy and it was very successful. We spent three months locked in Steve’s office saying no to every other thing at the agency—we totally became web geeks and I never looked back. That was it for me; it was a religious conversion. There were 3 million web users and 1.5 million came to see our website! I had done art, writing, and music and had never had the knowledge or networking skills to get my stuff out there, but with the web, I became a producer and publisher.
We published the site for Batman and I was in love with it. We had created message boards which we seeded with the beginnings of conversations so people wouldn’t get there and get scared. We were able to create full-screen backgrounds using repeating image tiles because Netscape 1.1 came out while we were working on the site. We had videos the size of a postage stamp that were 3MB and back then, you couldn’t stream—you had to download video. There was no Flash or animated GIFs yet, but we hired Doug Rice at Interactive8, a very early digital studio in New York, to write a Perl script that would replace one image with the next to give the effect that a bat was flying toward the viewer. Nobody had ever seen anything like that on the web. It was the precursor of the Flash intro and maybe the first one on the web. I later rallied against that type of thing, but I was one of the first to have a hand in it.
After we published the site, I learned about more rudimentary layout things we could do that we hadn’t done, like using tables to create actual margins for our copy instead of just wall-to-wall text. I sweet-talked the producer on the Warner Bros. side to give me the FTP password and credentials to get in to make some edits. I went in using Fetch and edited all the HTML to update the layouts…because I couldn’t just change the style sheet—CSS didn’t exist yet!
I was thrilled and totally happy with web work, so I kept doing it. I made a million mistakes and didn’t always know what I was doing, but I was in a transitional period of my life and had a lot of time to devote to learning. I was in a relationship, but my girlfriend was an artist and had her own stuff going on; we gave each other space to be creative.
The other part of my path is that I started teaching and writing right away. I loved writing and I was good at it. Plus, I thought that HTML was so easy that everyone in the world could learn it. I thought it was my responsibility to teach people and to pass my knowledge along. I didn’t foresee Twitter or anything like that, but I saw this platform that Tim Berners-Lee invented that would enable people anywhere in the world to communicate. They didn’t have to appeal to a government or publisher. They could create what they wanted to and put it out there, like you guys do with your magazine. I published all this information on my website for free and I started blogging, but I didn’t call it that. To me, blogging was a secondary activity. I thought I had to have a really entertaining website, so I created Mr Jenkins’s Last Martini, an alcoholic haiku contest, and I got to interview movie stars through Warner Bros., so I put those interviews on my site.
“…everything comes out of the product and just being clever isn’t good enough. You want to move people; you want to amuse them, entertain them, and make them think.”
Ryan: Was this all while you were still working at the advertising company?
Yeah. I initially kept the ad job while I started freelancing as a web designer and publishing stuff on my own.
Around the same time, Brian Platz and I started A List Apart, which began as a curated mailing list. We would absorb topic email all day and at the end of the day, Brian or I would identify the emerging theme out of the 700 items we got. It was a very early form of user-generated content, but it was edited. A year into that, I started the website for A List Apart. I designed it and it was really ugly—it was deliberately ugly because I had this weird, in-your-face, punk aesthetic because the web was underground and being a web designer was an underground activity. Also, I sucked at design. I did a lot of very cliche, club flier looking typefaces and made header illustrations for every article. Today we have Kevin Cornell doing these amazing New Yorker style illustrations—I say New Yorker to give people an idea of the elegance of them, but they’re totally Kevin’s own style. That was Jason Santa Maria’s idea. Jason said, “You used to do these header images. We should bring that back.” He introduced me to Kevin and now, I kiss the ground that that man walks on.
Our community wrote the articles and after a while, I started realizing that some of the people I knew were really smart and should become authors. People began contacting me to write books and I sent them on to others who I knew probably had a book inside of them. Basically, A List Apart functioned as a breeding ground for writing talent, developers, and designers who were innovating and could express themselves.
About a hundred issues in, I got an email from Erin Kissane. She was really young and I think she was in graduate school at the time. She said, “I hate to bother you, but there’s a typo in this article.” I said, “Thanks. I’ll fix it.” Then I got another email from her about a typo and then one about a grammatical error. I said to her, “Do you want to be my copy editor? I can’t pay you.” I expected her to say no. It was a taunting way to say, “Lay off, unless you’re serious. If you’re serious, I really want this help.” She said yes and she worked for years with no pay. About six months into her copy-editing apprenticeship, I said, “You should be the editor. You’re not a copy editor—you’re an editor. You’re really brilliant.” Of course she knew that, but she didn’t come in and tell me that. She was editor-in-chief for six years and then when she stepped down, she helped me find Krista Stevens and Krista helped me find Sara, our new editor.
If you go to the A List Apart about page, there’s a central column that lists all the people who work on it now and who have worked on it and it’s really a who’s who. All those people were young and not well-known at the time, but they were always somebody and they had all these great ideas. A List Apart has been a school for all of us to learn from each other.
“I had done art, writing, and music and had never had the knowledge or networking skills to get my stuff out there, but with the web, I became a producer and publisher.”
And the An Event Apart conference grew out of that same community?
The An Event Apart conference grew out of the magazine, but it started with conversations I had with Eric Meyer, who I kept running into on the road. Every year during SXSW Interactive, we used to meet up for breakfast at this small place called Las Manitas, which no longer exists. It looked like a traditional diner in the front, but if you walked through the kitchen, there was a backyard where you could eat. I’d go out there and see Lyle Lovett having coffee at one table and Doug Bowman at another table. It was a serendipitous and wonderful time where all these amazing musicians, filmmakers, and web people came together in one place.
I was also lucky enough to be meeting people through my publisher, New Riders. Michael Nolan, the guy who hired me to write, would take me and other writers out when we were on the road speaking at events. That’s how I met people like Dan Cederholm and Ethan Marcotte, who was hanging out with Dan at the time—he was probably 12 years old. I always think of Ethan as little because he’s much younger than me, even though he’s so tall that whenever we stand together, I look like his strangely aged child. I remember going to dinner with Ethan and he didn’t even open his mouth. He just sat there listening to people and raised his eyebrows every now and then. I thought, “He’s the smartest guy in the room. I’m going to work with that guy.”
Sometimes you just know these things, right? I had that same feeling with Jason and also with Mandy Brown. She was a Happy Cog client and I was just so impressed with her. She was working at this really important and wonderful publishing place, but it was pretty traditional and she was kind of restricted in her freedom to be Mandy. I thought she was the smartest person and I knew I wanted to work with her. If I have a gift, really, out of everything I do, it’s recognizing when other people have profound hidden talent, figuring out who should work with who, and introducing people to each other. Really, that’s the best part of all of what I do.
Anyway, back to SXSW—every spring, Eric Meyer and I would meet for breakfast and say, “You know, we should really run a conference.” We’d be speaking at conferences and have ideas about how to make it a better presentation and experience. Before then, it never occurred to me that I could run a conference or a business. At that time, I was freelancing and Happy Cog was just me. I wasn’t sure I could put people together to run a business and also, I was raised by an armchair socialist and had a love-hate relationship with the very idea of business. But Eric and I decided to do the conference. Jason Santa Maria found us a venue that seated 150 people; a friend did the sound; there was no wi-fi; Jason was one of our presenters and he was so nervous that he read from his paper—now, he’s one of the best speakers I’ve ever seen—and people actually came to our event and it was awesome.
For the next year, we did events in different cities and always made sure to have a local hero or heroine. Then we realized we were tired of picking venues ourselves, so we reached out to someone named Marci Eversole, who runs events. We had a very limited idea of what she could do for us and no idea that she could totally transform our business. She said okay because she’s really smart and never says no to a job simply because it is small. She booked us a gig at the Alamo Drafthouse and then asked us if we’d consider holding the conference at a hotel because the event had sold out so fast and there were many more people who wanted to come. We felt like hotels were too corporate and she agreed, but suggested that we were the show and there were things we could do to make even a hotel feel cool, plus hotels had catering and wi-fi. She was persuasive and offered to work up a budget for us. Now that’s what we do—next year we’re doing eight shows in eight cities, all but one in hotels. They’ve become like these little mini-festivals.
Doing the conferences does take a lot of time away from the family, which is a drag, but I have to do it—I have an expensive divorce and a young child who needs to be able to go to college someday if she wants to. Soon I’ll be old—I’ll never be too old to work, but soon, it’ll be scary to have me on stage, so I have to get out there and hustle now while I can.
One of the questions we ask is if you had an “aha” moment along the way. Was creating that first website the moment for you?
Creating the Batman site was most definitely it. I finally knew what I wanted to do for the rest of my life.
Did you have any mentors along the way?
I had some really brilliant mentors in advertising. There’s a creative director, Sal Devito, who has won all kinds of awards and teaches at SVA. He wouldn’t tell you what was wrong with your idea—he would just throw it into the garbage until he found one that was worthy. After a while, I realized what Sal liked by concentrating on what he approved of or smiled at because he wouldn’t tell you and he didn’t do all that encouraging pep talk stuff. I thought, “This guy is so brilliant and I’m not half as brilliant, but if I ever become a creative director, I want to be more encouraging.” I’m a nurturer. I always want to let people know when I think they’re doing a great job.
I got sober 19 years ago and one of the things they said was to be really active in your program and help someone else—that’s what keeps you sober. This was in 1993 and in 1995, I became a web designer. I applied the stuff I learned in the 12-step program to my business by helping other people and reaching out to them. I don’t think this whole empire of Happy Cog, A List Apart, An Event Apart, and A Book Apart would exist if I hadn’t done that, but I didn’t do it thinking I was going to get a payback. I believe that’s how it works; you do stuff, try to get better at it, be friendly to people, and the good you do comes back to you.
“I walked away from that [job] feeling really liberated and free. Money wasn’t the most important thing and now I knew it. I had always said that, but now I believed it…”
Have you had a point in your life when you decided you had to take a big risk to move forward?
Yes. I was a creative director at this dot-com in 1999. The people I worked for were really nice and I’m still friends with them, but there were things about the business that I didn’t understand or like. There was money flowing in and it was unreal. I understand charging for a service, but I didn’t understand where all this money was coming from and it didn’t feel sustainable. I thought, “I should just stop working for these people and do this for myself.” They said, “If you stay one more month, you’ll be vested and you’ll have stock in the company.” I said, “I know and I really appreciate that, but I gotta go.” It was probably stupid, but it was an emotional decision.
When I went out on my own as Happy Cog in 1999, I had one client and it was a consulting gig. It was a community for moms and they were trying to professionalize it. There was money involved and when they brought me in, they had just hired an editor who was a really good print world editor, but hadn’t paid much attention to the web. Like a lot of editors, she had a tough ego and a combative, prove-it-to-me attitude. I was hired to help them create a viable web community, but we never got past Web 101 because the editor challenged everything I said. It could be something as simple as suggesting we go with a sans serif typeface to make it easier to read. She said serifs were easier; I said not on the web. Remember, this is way before OS X and Cleartype. My client never took my word for even the simplest assertions; she wanted evidence for everything, so I’d have to do homework every night, and Google didn’t exist yet. Arguing over little things instead of doing my job and helping her achieve her strategic goals felt degrading to me.
It was January and this was the only gig I had. My rent was $2,000 and I was getting paid $1,000 a day, which is more money than I had ever earned in my life, but I hated going in there because it was combative. On the fourth day of working on the project, I was walking to work in the snow and thinking to myself, “You shoveled driveways for a dollar an hour in Pittsburgh as a teenager, so just shut up and take the money,” but I couldn’t do it. A few hours into the day, I said to the editor, “I don’t think this is working out.” I made it my fault and said I wasn’t the right person for the job. I walked away from that feeling really liberated and free. Money wasn’t the most important thing and now I knew it. I had always said that, but now I believed it and Happy Cog has stayed that way. We don’t do things we’re uncomfortable with. We have to believe in the product or service and feel like the people we’re working with are honest or we won’t accept a project.
Do you feel a responsibility to contribute to something bigger than yourself?
Yeah, I absolutely do. For example, one of the things A List Apart and An Event Apart do together each year is run a survey for people who make websites. Through the survey, we hope to paint the first true picture of the profession. If you follow the tech press, they’re interested in other things, like which browser is the most popular. They don’t care about the people who make the web. We want to know who is doing the work; what they’re getting paid; if men and women are getting paid the same; and lots of other stuff. Somebody’s got to find out these things; turns out, we’re the somebody.
I also feel an obligation on my site and on Twitter to constantly call people’s attention to anything good that I come across. For example, Contents Magazine just brought up an important issue—what responsibility do companies have to us regarding our data? If Instagram goes away, do I lose all my pictures? If Facebook goes away, do I lose all those conversations? I was a huge fan of Gowalla and when it disappeared, where did my data go? I remember paying some exorbitant fee to use my phone while in London so I could check into Buckingham Palace on Gowalla. There are memories attached to these apps; this is where we live part of our lives now, and it’s how we share with family, friends, and the broader community. People mourn when an app disappears. Contents introduced three simple guidelines to help and what I’m going to do today is share that article with some friends at a few companies that make social apps and ask if they’re thinking about this and if they have a plan. I want to reach out in a friendly way to anyone I can to further the conversation.
Of course, I have a daughter now and that’s way bigger than me. Having a kid has changed everything. To me, my own death stopped mattering as long as she’s okay. I almost got hit by a truck on the way into work today. I was crossing the street and the driver started turning toward me—I’ve been hit before, so I should be more careful, but I kept walking. I figured he would stop, but he didn’t and it was a gigantic truck that clearly would have killed me. I looked at the driver like, “Fuck you!” and he looked at me the same. Luckily, he stopped at the last minute—it was like New York street chicken. I won.
Tina: You also share some personal writing on your site. Are you hoping to contribute anything through that?
I don’t know. I might do this book, Little Jeffrey, Happy at Last—I keep thinking about it. The problem is that I write memoirs. That’s a good thing to do if you’re a famous person or if you’ve lived an exemplary life in some way, but to me, my story doesn’t have some overarching heroic point. It would just be a bunch of messed up incidents with little life lessons.
Are you satisfied creatively?
Never. I get excited about what we’re working on, especially at the beginning of a project, but I’m always a little dissatisfied when it’s finished—not the internal stuff because you can keep redoing that. On big projects with lots of parts, UX people, wireframes, and all these requirements, it’s hard to make a simple, moving experience. I think we do a really good job of putting everything together, but I’m always a little disappointed. That’s just me; I see the mistakes in everything I do. I also think we’re at the very beginning of where we’re going to go with the web and there’s a lot of room to grow.
Any plans for the next 5 to 10 years?
Well, we’ve been building a nice library with A Book Apart. I trust that we’ll have 20–30 books and that some of them will be considered classics and part of the canon. We’ve been very lucky so far in picking really brilliant people at just the right moment when they have something important to share with the community. It’s like picking fruit when it’s ripe. How long we can keep doing that? I don’t know.
There are a lot of features we’re adding to A List Apart, but we’re rolling them out slowly, partly because of budget and partly because we want to carefully add features so we don’t lose our focus. Diversification is great, but we don’t want to lose the things people love about us.
Then there’s Happy Cog Tokyo and Happy Cog London. Have I said too much?
And there’s the conference—I don’t know how much more awesome that can get, but it feels more exciting and more focused each year.
I’d like to do something with architecture too. I just started a page on Foursquare that’s all about buildings in New York that I love. I have a classic text by Paul Goldberger called The City Observed: New York, which is now out of print. The author is still alive and I thought it would be cool to get his permission to take new photos of each building in his text, give each building its own web page, and tie it all into Foursquare. You could essentially go from building to building and discover the history—who designed the building, what compromises were made, what changed over the years. That’s interesting to me and there are only a few cities where you could go to town with an idea like that.
If you could go back and do anything differently, would you and what would it be?
Well, I live my life as if everything happens for a reason. I don’t know if that’s true, but I choose to believe it’s true. You know, I’m sad that my marriage didn’t work out, but I wouldn’t give up that marriage and I certainly wouldn’t give up my child.
I wasted a lot of years being underemployed and not knowing what I wanted to do. I wasted time working on things that weren’t the Internet because the Internet wasn’t around, but I developed other skills. I had a job washing dishes at a vegetarian restaurant called The Earth Kitchen (for real!) and every night I would dream that I was washing dishes. I’d see peas and carrots swirling around in soapy water in my dreams and then I’d get up and wash dishes. Having done that really makes me appreciate what I do now.
Tina: Where was that?
That was in Bloomington, Indiana, where I went to undergraduate school.
Tina: Where did you grow up?
We moved a lot. I was born in Queens and when I was four, my family moved to Long Island. When I was eight, we moved to Connecticut and at thirteen, we moved to Pittsburgh.
You have a lot of experience under your belt. If you could give a piece of advice to someone just starting out, what would you tell them?
Write. You don’t know what you think if you don’t write. And teach. At least teach your coworkers some new technique you learned today.
Another thing—don’t be afraid to ask for help. I sucked at Flash and I’m glad web standards won for many reasons, but one selfish reason is because I found Flash unpleasant to use as a creative tool. I simply didn’t understand it well enough, but I was at a professional level where I couldn’t go to a community college and take a Flash course. Someone would say, “There’s Jeffrey Zeldman taking a remedial Flash class.” You have to find a way to keep learning and not get trapped in whatever imaginary status you have.
It’s an ecosystem—you give tips and get tips. That’s what is so amazing about our industry as opposed to other creative businesses. I did enjoy advertising in some ways, but it was very secretive in nature and the design and web culture is not like that at all. That’s the joy of our profession—you get that childhood feeling of being able to be creative and share freely with others.
How does where you live impact your creativity and is it important for you to be part of a creative community of people?
I live in New York and I’m sure my work would be very different if I lived somewhere else. The New York street grid influences the way I think. New York’s verticality influences how I design. The energy of the place is amazing—I walk fast, I think fast. There are constantly young people coming to have an opportunity to renew themselves and be around other creative people. It’s less lonely here. I think you can be creative and do web stuff anywhere, but it might be more lonely in some places because it’s harder to find your tribe.
What does a typical day look like for you?
I get up early and try to get as much as I can done. If my daughter is with me, I take her to school and then go to the gym to work out with my trainer. I come into the studio and work for a few hours and then have lunch with somebody—that’s another part of community. It’s more comfortable to eat at my desk and keep working, but I try not to do that too much because one day I’m gonna die and I’m not gonna say, “Man, I should’ve sat at my desk and eaten lunch alone more often.” I work until it’s time to pick up my daughter and then we go home and she plays. Sometimes we watch a film or she watches My Little Pony on her iPad and I pretend to watch it while looking at my iPhone. I’ve turned her onto really old stuff like The Marx Brothers, which she loves, as well as Betty Boop and Popeye. She’s seven and she asks, “This came out when you were a kid?” I reply, “No, this came out when Grandpa Murray was a kid.” Around 9pm, I’ll read to her and put her to bed and if I’m lucky, I’ll stay awake after that to read.
Current albums on repeat?
MF Doom and all his aliases—Viktor Vaughn and KMD; David Bowie; Brian Eno; The Roots; John Coltrane. I’m on Last FM.
What’s your favorite movie?
Your favorite book?
All the Harry Potter novels.
Do you have a favorite food?
My favorite food is changing because I’m eating healthier now. In the past, I would have said pasta, but now I eat salads of various kinds and salmon.
One last question—what kind of legacy do you hope to leave?
Wow! Well, I hope I was a good father.
People come up to me and say, “Your book changed my career,” or, “A List Apart really helps me feel not alone because I’m the only web person at my company, or the only web person who gets it at my company.” I hope that kind of stuff can continue and that I will have touched some people. I hope I’ll write something that people still read and I hope people will say, “He helped me.”
“If I have a gift, really, out of everything I do, it’s recognizing when other people have profound hidden talent, figuring out who should work with who, and introducing people to each other.”