Ask Me Anything: @zeldman, here

4 years ago from , Principal, Creative Director

What would you like to know? What problems do you struggle with in your design life and career? What are your thoughts about web and product design?

Or, you know, just say hi.

Here’s a little something about me:

Designer, writer, publisher, speaker, founder. Principal and Creative Director at Automattic, makers of WordPress.com. Blogging since 1995. Founder: A List Apart for people who make websites (1998), Happy Cog™ studio (emeritus) (1999), and studio.zeldman.

Publisher and co-founder, A Book Apart – brief books for people who make websites. Co-founder, An Event Apart design conference. Author of foundational web design text, Designing With Web Standards, currently in 3rd edition coauthored with Ethan Marcotte, translated into 15 languages.

Host, The Big Web Show podcast (“Everything Web That Matters”). Faculty, MFA Interaction Design program, School of Visual Arts NYC. First-ever inductee to the SXSW Interactive Hall of Fame.

Whew. That was a lot.


  • Nik RajpalNik Rajpal, 4 years ago

    How do you deal with heartbreak?

    9 points
    • , 4 years ago


      The Serenity Prayer is pretty wise about this stuff: “Grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.”

      Then again, there are the kinds of heartbreak where what happened is/was simply unacceptable. Like the death of a child. I don't know how those who've experienced that find the courage to go on.

      There's heartbreak and there's heartbreak. A romantic breakup nearly killed me at 21. At 50, I was stunned and distressed, but I recovered more quickly.

      Some heartbreak is inevitable. The decline and death of a parent.

      If you can possibly avoid hurting yourself, do. Reach out to friends. Ask for help. Maybe get therapy. Exercise. Do yoga.

      Don't handle heartache with booze or drugs or self-destructive behaviors. Don't hurt you to hurt the pain that is hurting you.

      It’s hard to love yourself when someone you love rejects you ... but that's when you have to learn to love yourself the most.

      I hope you are okay. I hope this helps.

      27 points
  • Bryan Maniotakis, 4 years ago

    What are your thoughts on the rise of codeless site builders like Webflow?

    7 points
  • Yo Yay, 4 years ago

    How do you stop comparing yourself to others?

    4 points
    • , 4 years ago

      To some extent, you can’t. It’s human nature to compare ourselves to others.

      Designers are competitive, and we often suffer from imposter anxiety, so it’s easy to see the many flaws in our own work, and to see nothing but beauty and genius in someone else’s. No matter what we achieve, it’s never good enough. Why can’t I make something as great as what so-and-so made?

      In some ways this competitiveness is healthy: it pushes us to work harder, do more, not be satisfied with our B- efforts when we might really have an A+ effort in us if we work a little harder.

      In other ways, it’s just self-defeating thought patterns we subject ourselves to how we grew up. We should stop doing that to ourselves if we can. For instance, just as an example: Why does X design better icons than I do? Maybe because X is better at designing icons and I’m better at figuring out customer journeys. No one since Leonardo DaVinci has been great at everything. Even Mozart couldn’t dribble a basketball.

      Let’s recognize and be proud of the things we’re good at, not just beat ourselves up over the parts where we’re less gifted. Let’s use the confidence we gain from acknowledging how good we are at customer journeys to either give us the courage to practice and improve our icon design, or the honesty to collaborate with an icon designer who’s not as good as we are at customer journeys. Design is a job and it’s also a team effort.

      Your question is fairly open-ended and there are many other ways I could answer. For instance, your question might be, How can I, the only woman on this team, stop comparing my position and salary to those of my colleagues (if all of them earn more money and have better titles). And the answer, there, is that you shouldn’t stop comparing. You should fight for your rights.

      Or the question might be, how can I stop comparing myself to my favorite designer? And the answer might be, you may not have to do so. Maybe your favorite designer does the kind of work you know you will be doing in two years. When you study their work, it’s a form of apprenticeship. So acknowledge that and use it, and get better. You can even copy what they’ve done (as long as you don’t publish it—copy privately, for your own educational purposes only). When you’ve mastered that other designer’s voice, you can put the obsession behind you and begin to create your own unique voice. (Which is probably more awesome anyway.)

Hope this helps!

      7 points
  • Justin Gagne, 4 years ago

    Hi! Big fan! Ahem… If you were to publish a new book, what would you write about?

    3 points
    • , 4 years ago

      Hi, Justin. That’s a great question.

      I sometimes wish I had the time and resources to write a fourth edition of Designing With Web Standards. Not because I want to spend a year of my life, like a monk, isolated in a writing booth. :) But because I worry about the direction our industry is going. There are many incredibly exciting things happening in web & digital product design, as you know. But along with that progress has come a Great Forgetting™ of the basic and vital lessons of accessible, semantic web building. It’s DIV soup and long strings of classnames and everything in JavaScript ... and it worries me.

      HTML and CSS were made for progressive enhancement. These other tools, at best, "gracefully degrade." If that. We’ve brought back a lot of the terrible assumptions of the earliest period in web design, when web experiences were for people who had the right equipment, the right connectivity, and the right physical and cognitive abilities. That's a step back. Even with all the whizzy neato cool shiny stuff we can now do, if we’re leaving people out because of our biases and assumptions, we’re not building a future any of us should want to be part of.

      So there's that.

      A lot of great people are carrying the lessons of accessible, standards-based design forward in their talks and their books, so even though I'm not in a place where I can write DWWS 4th Ed., I'm confident that my smart colleagues are getting the message across (including at conferences like An Event Apart and in A Book Apart books I publish).

      Currently I'm interested in slow and fast design. I'm particularly drawn to slow design and its relationship to readability. It’s what I'm speaking about now. It also influences the work I'm doing. Perhaps there is a book in that.

      Recently my daughter and I wrote a story for a children's book that is being sold to raise money for UNICEF. So that's pretty cool. Another children's book, maybe a short work of fiction or even autobiography. On the one hand, autobiography seems extremely narcissistic, and I'm not sure the world needs another story about how someone like me grew up. On the other hand, the specific is universal, and the more I share about my weird life, the more other people with very different and unique stories could somehow relate. So I think about that.

      At the moment I'm very happy with the work I do at Automattic, so I don't have the lust to write another book. And it takes a strong desire to make yourself write a book!

      5 points
  • Nick Dominguez, 4 years ago

    Just wanted to say thanks for writing "Designing with Web Standards" it was a pivotal book for me and my career at the time it was published.

    2 points
  • Afnizar Nur Ghifari, 4 years ago

    Hi Jeffrey! I have two questions for you :)

    1. What activities/hobbies do you partake in outside of work?
    2. What book did you last read and would like to recommend to a young designer?
    2 points
  • lisa dziuba, 4 years ago

    With all your activities, how do you keep the work-life balance?

    P.S.: we are good friends with Automattic iOS engineer Eduardo Toledo, just met him in Ukraine

    2 points
    • , 4 years ago


      Nice to meet you, and hey to Eduardo! :) 

      First I’ll answer generally, and then specifically (i.e. how I do it with my specific things).

      Generally speaking, you have to prioritize what’s most important to you, let go of the small stuff, learn to say no, and stop working on side projects or ask for help to keep them going.

      In my case, I ask for help. And it works.

      So. I’m a full-time dad and a full-time (and busy!) Automattician, and those are my full-time, day-in, day-out focuses. The rest is possible by having great teams, trusting them to do what they do, and checking in with them as frequently as need be. 

      For An Event Apart, there’s a lot of editorial work to be done choosing the best speakers, helping them hone in on the most relevant topics, and arranging those topics editorially in each AEA conference. I can’t hand that work off. It needs me. I email and meet weekly with staffer/producer/editorial consultant Toby Malina and partner/co-founder Eric Meyer, and reach out to speakers via email and calls as needed. The billions of hours of additional work needed to mount a successful conference are handled entirely by the brilliant Marci Eversole. I trust her with my life.

      The conference enhances the knowledge I’m able to bring to my work at Automattic, since I’m constantly interacting with and learning from some of the very best designers, developers and strategists in our industry. Automattic is an open source company dedicated to democratizing publishing and sharing knowledge. An Event Apart is about sharing knowledge about the open web. The values are in sync, and the time I put into An Event Apart, although it’s done outside of Automattic business hours, is in some ways, conceptually, also work I do for Automattic.

      A List Apart functions because of the brilliance and hard work of our crew, including Aaron Gustafson, Michelle Kondou, Brandon Gregory, Mica McPheeters, Dougal Macpherson, Tatiana Mac, Adrian Roselli, Rachel Andrew, Dezzie Garcia, Sara Wegman, and many other extraordinarily gifted people (all listed on that Masthead), who review submissions, work with authors to fine-tune them, and manage the many other tasks that go into creating a low-volume, high-quality web publication. All I need to do is read the article drafts and weigh in on the discussions as to their merits. That’s something I’d do for pleasure anyway. It takes less time than I spend watching TV or going to the gym—because the team is that good, and their collective intelligence is that powerful.

      Since moving from our old platform to WordPress (with the incredibly able assistance of Tiffany Bridge and the Automattic Special Projects team, which is how I fell in love with that team, and which led indirectly to my taking a job there), we’ve also been able to bring our Italian publication edited by creative director Valeria Brigatti in-house, instead of treating it as an external publication. Again, all I had to do was say, “Yes, please.”

      A Book Apart is, I think, an important addition to the canon of great books for people who design, write, and code. I co-founded it with  Jason Santa Maria, and in the beginning, we were very busy setting it up, but today, and for several years, CEO Katel LeDu has done EVERYTHING. Jason and I weigh in a book proposals and give Katel our thumbs-up when she proposes big changes to how the company works, but it’s really all Katel and her staff and consultants at this point. 

      I could not run the three Aparts myself. I could not even run one of them myself. Finding good partners. People worthy of trust. People with talent and work ethics you can depend on. That’s the secret.

      2 points
  • ChrisArchitec t, 4 years ago

    Thanks for coming by Zeldman! Blue beanie represent

    What do you think about the complexity of modern web design as far as the multitude of frameworks and basically totally different approach with technology stacks like React/JAMstack etc etc and relation to the core web standards

    2 points
    • , 4 years ago

      Blue beanie represent! Thanks for asking, Chris.

      Back in May, 2018, I wrote The Cult of the Complex in A List Apart to express my frustration with the feeling that toolchains were replacing know-how, and that web making was becoming a d*ck-measuring competition: “If we wish to get back to the business of quietly improving people’s lives, one thoughtful interaction at a time, we must rid ourselves of the cult of the complex. Admitting the problem is the first step in solving it.”

      My theory was that chasing the new for its own sake, and to prove how good you are at your job, was a distraction from our real job of removing our own biases, figuring out what our customers actually need, and relentlessly focusing on the hard task of solving our customers’ problems. Solving customer problems isn’t as sexy as slinging tech, but it’s our real job and it’s where true satisfaction for designer and customer alike resides.

      That said, some of the change we’re seeing now is good and important and worth struggling through if it helps us bring better products and experiences to our customers. I talked about my own struggles learning new things after decades in the industry in “You Got This” on Automattic Design this year. Some of my resistance to the shiny new is because it’s a distraction. But admittedly, some is also because learning new things is hard, and gets harder as you get on in life and your career. (Learning new things about your work after 20 years in a field is harder than learning new things when you’ve been on the job for only a few months because after 20 years you also have things to unlearn, whereas in the beginning you’re a blank slate.)

      So I’m all for change for personal growth’s sake and when it benefits the customer (for instance by allowing you to create affordances you couldn’t create in the past).

      But I oppose throwing out future-focused, progressively-enhanced, accessible, semantic markup and lean, well-optimized CSS (with only the JavaScript that is absolutely necessary to deliver niceties that are delightful but not essential to the experience). That is the bedrock on which our whole web is built. It matters.

      4 points
  • Justine Shu, 4 years ago

    Hey Jeffrey! What are your favourite website designs right now?

    2 points
    • , 4 years ago

      Hi, Justine. Thanks for asking.

      A site my Special Projects team at Automatic is finishing for Om Malik is one of my favorite web designs at the moment, but it hasn’t launched yet, so I can’t share it with you. ;)

      I’m a sucker for good editorial design on the web. From a pure web-layout-appreciation point of view, I loved medium.com the first time I saw it. To me it seemed to be a refined marker in the evolution of editorial article page and blog post page design that a lot of us had been working on for nearly two decades at the time. It was readable, which means not just legible but actually engaging. It used big type and type hierarchy very well, and presented authors with great but simple choices to tell their stories effectively. 

      I loved it in 2013 the same way I loved Douglas Bowman’s “Minima” theme for blogger.com in 2003. It had the same “understated state of the art” quality to it: not the shiniest and newest radical new thing, but rather a refinement of all the best things that were already out there. 

      For innovation and outside-the-box thinking, I love where Jen Simmons is taking web layouts in her Experimental Layout Lab.  (Scroll well below the fold on most screens to see her demos for 2019, intro to CSS Grid, studies on flexibility, overlap, viewport, whitespace, and much more.) If you’re a front-ender who designs as well as codes, Jen Simmons’s Lab should be your № 1 bookmark for new ideas in web layout.

      Also for coding designers, designer/consultant/type futurist and author Jason Pamental publishes a newsletter on web typography which is well worth subscribing to and in which he has begun designing demos of what we can now do with variable fonts and modern CSS.

      There is so much great work being done right now—and so much work looks like so much other work—that it’s hard to pick favorites. For pure visual pleasure and usability, I still love https://dribbble.com/. That is, I love the actual site (how it looks and works) as well as the incredible work it showcases.

      And of course, when seeking design inspiration, a great place to start is always Designer News. ;)

      7 points
  • Matthew Hollingsworth, 4 years ago

    Thanks for being here Jeffrey! Really appreciate you taking the time.

    Is there something you know now that you wish you knew when you first started out as a designer?

    2 points
    • , 4 years ago

      Thanks, Matthew. Tricky question. I wish I had known, when I started, that design is about the user ... about what they need to do. It’s not about showing how clever or skilled I am. It’s about other people's needs, not showing off my talent.

      I wish I had known that when I started, but almost nobody knows that when they start, and maybe if we knew that from the beginning, we wouldn't even have been attracted to the work in the first place.

      I needed to show off my first few years, while I was building skills and learning fundamentals. Some of that early showing-off work, in spite of how extremely dated it is (centuries old in Internet years) still delights me in ways the more mature work I do now doesn't.

      So it’s a tricky question because, in a way, we learn what we are supposed to learn when we are supposed to learn it. We go through phases in our work the same way children grow. Children are supposed to play before they become adults who work. Designers are supposed to indulge themselves while they are learning the art and science of their craft.

      So, really, as a designer, I learned everything when I was supposed to, I'm grateful for my many mistakes (even the ones that cost me jobs), and I'm happy to be exactly where I am. I wish the same for everyone.

      5 points
      • Matthew Hollingsworth, 4 years ago

        Beautiful, thank you.

        Follow up (and potentially more difficult) question: Do you think there's a unique attribute that you have that has allowed you to get to where you are in the design world? Is there a skill that people overlook when it comes to progressing as a designer?

        2 points
  • Matthew Smith, 4 years ago

    What were three harder lessons you learned about running a design studio?

    1 point
  • Ali Zendaki, 4 years ago

    You have inspired me to be what I am today. I have followed you since when I was creating Geocities sites on a WebTV back in the super early 2000s. I will never forget all you have done for the web and individuals like me. Thank you from the bottom of my heart. -Ali

    1 point
  • Ravi Shanker, 4 years ago

    Hi Jeffrey!

    I look forward to class this year.. (IXD, Class of 2020)

    1 point
  • Radley OrdestaRadley Ordesta, 4 years ago

    Can you send a Dribbble invitation? please? :) -radleyordesta@gmail.com

    0 points
  • Nader KeshavarzNader Keshavarz, 4 years ago

    Dear Zeldman How you do clean your laptop display?

    0 points
  • Matthew Hollingsworth, 4 years ago

    Hey folks! Big thanks to Jeffrey for taking the time to answer some question from the community.

    We're at the end of the designated time for the AMA. Thanks to everyone for taking part! Jeffrey -- completely up to you if want to answer any questions from here on out, but absolutely no expectations from our side!

    Thanks again!

    0 points
    • , 4 years ago

      Hey, Matthew. This was wonderful.

      No new questions have come in, so </zeldman>.

      4 points
      • Tyson KingsburyTyson Kingsbury, 4 years ago

        damn...did i miss you?

        no new question here anyhow, just wanted to say thanks for all you've done for the past 2 decades or more now... can't even begin to tell you how much it's all appreciated :)

        I had the opportunity to meet you WAY back when, at AIGA in Miami, at the Eden Roc... I think we spoke a few times, and I was the one that spotted you that first night as you were checking in... i confess, as a design geek, the main reason I even went to that event was to get chance to chat with you and see your presentation...

        and damn..I still tell people about it to this day.

        as i recall, there was some kind of technical glitch, and things weren't working right, so you just started talking to us.... i think it opened up with 'so i was out scoring some crack, and left my baby in the back of the car...and the car was stolen..'

        DAMN.... did that ever get everyone's attention.

        it was an excellent introduction into the idea of having your website tell a proper story...and it definitely made a huge impression.

        anyhow, once again...thanks for everything Jeffery. From the first moment I saw 'steal these icons' and the ad graveyard, i've been a huge fan :)

        cheers Tyson

        4 points
        • , 4 years ago

          I remember you very well. You asked about my mom, who had recently passed away. How are you doing? :)

          3 points
          • Tyson KingsburyTyson Kingsbury, 4 years ago

            :) you wouldn't believe the grin on my face right now... so happy to be remembered :)

            I'm doing just great!

            My wife and I (when we met, we'd only been married a year or two) just celebrated our 20th-anniversary last week. My kids are both teenagers now.

            I'm with quite a few of the same people I was working with back when we meet at AIGA, doing software design and consulting... the work has been very rewarding, as I've gotten to learn UI/UX over the years, and am able to balance both the Creative Director work (marketing, brand etc) of the company, along with doing some UI/UX work on our product line which has been a tremendous amount of fun.

            How about yourself? How's the family?

            3 points