I'm Jason Santa Maria, design director at Vox Media, co-founder of A Book Apart, author of On Web Typography, and faculty at SVA IxD. Ask Me Anything!

2 years ago from , Design Director at Vox Media, co/founder at A Book Apart, author of On Web Typography

Hi everyone! Happy to be here answering questions for the next hour or so. Here are some relevant links for me: My personal site, Vox Media, A Book Apart, On Web Typography, SVA IxD, and Smart Quotes for Smart People.

37 comments

  • Jonathan CutrellJonathan Cutrell, 2 years ago

    Jason,

    I've got quite a few questions for you, but I'll limit it to two.

    1. I think it goes without saying that you've contributed to all of our stories. Can you share one or two of the most memorable moments in your career with us? It can be memorable for any particular reason. (I think these stories and memories inspire all of us.)

    2. Do you have any specific routines or habits that you follow with little variation?

    P.S. I'd love to have you on Developer Tea sometime, if you're interested. :)

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    • Jason Santa MariaJason Santa Maria, 2 years ago

      Thanks, Jonathan!

      I think it goes without saying that you've contributed to all of our stories. Can you share one or two of the most memorable moments in your career with us? It can be memorable for any particular reason. (I think these stories and memories inspire all of us.)

      That's very kind of you to say. It means a lot to me if my work can help inspire as I've drawn so much inspiration from others over the years. I'll share a bad story form my past:

      When I put in my two weeks notice at my first job (which I loved and learned a ton at) I was asked by my employer to cover the cost of my health coverage for two weeks. It was just the way it was setup, there was an overlap in the way it was scheduled and with my departure that left the two weeks uncovered. For some reason I thought I needed to make a stink of it and tell them they needed to cover the cost, and I did it in a rude way. We're talking about like $100. Needless to say, I upset them and burned a bridge badly.

      I was so wrapped up in my own departure that I thought it was their problem. I acted like an entitled idiot and hurt people I loved and learned a great deal from. Even after a bunch of time has passed I think back on that and feel ashamed. I learned a lot from that experience about how to conduct myself and how to just have respect and empathy for everyone you encounter.

      Do you have any specific routines or habits that you follow with little variation?

      I guess the biggest one is waking up in the morning. I used to work a lot late at night after work. I would read and learn to program different things, or just try and design new things outside of client stuff. But over time I found that I worked much better in the morning hours. I try to get up as early as I can (usually around 6) so that I can get a jump on the day. Sometimes that's going to the gym, sometimes it's design work. That's when my mind is sharpest and I can think through ideas most critically. Then as my energy tapers off throughout the day I tend to less mentally taxing things (like email).

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  • Nick HNick H, 2 years ago

    I'm Daenerys Targaryen, the First of Her Name, Queen of Meereen, Queen of the Andals and the Rhoynar and the First Men, Lord of the Seven Kingdoms, Protector of the Realm, Khaleesi of the Great Grass Sea, called Daenerys Stormborn, the Unburnt, Mother of Dragons.

    Ask me anything

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  • Jeff WolffJeff Wolff, 2 years ago (edited 2 years ago )

    Hey Jason thanks for doing this! I recently got a new version of On Web Typography the other day. Did you add any new content or was it purely spelling/grammar changes?

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    • Jason Santa MariaJason Santa Maria, 2 years ago

      Thanks Jeff!

      I recently got a new version of On Web Typography the other day. Did you add any new content or was it purely spelling/grammar changes?

      Woo, thanks for reading! Nope, this was just an errata update to fix typos and errors in the initial release.

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  • Tunde Adegoroye, 2 years ago

    How do you usually tackle projects & any advice for beginner designers i know its two in one haha sorry

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    • Jason Santa Maria, 2 years ago

      Hi Tundle!

      How do you usually tackle projects

      Whenever possible, by talking to people. That could be whoever requested the project and/or the people the project is aimed at. Information gathering is the detail most often overlooked by designers.

      & any advice for beginner designers i know its two in one haha sorry

      Immerse yourself in what you want to do. Read and challenge yourself often. Practice as much as you can stand without burning yourself out. And don't live in front of your screen; design need to happen in your head first, not in an application.

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  • Jeremy StewartJeremy Stewart, 2 years ago

    No question. Just wanted to say that you've been an industry hero of mine for a long time. I really appreciate how much you've shared over the years. It's helped me and the community more than you know!

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    • Jason Santa Maria, 2 years ago

      Thanks very much, Jeremy! It means a lot to me to hear that, I really try to share as much as I can when I'm able. It's the way I learned from others on the web, and I've always considered it everyone's responsibility to contribute. Here's to sharing!

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  • Skyler B, 2 years ago

    Hi Jason,

    Thanks so much for being here and answering questions today! Your work is fantastic and it's awesome to gain more insight into your thoughts and process.

    I'm curious about your current role at Vox. What were the biggest challenges and most rewarding parts of transitioning to in-house work? And it's clear that you're still pushing great design and design vision forward; has working with the Vox team changed your perspective or your design process at all?

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    • Jason Santa Maria, 2 years ago

      Hi Skylar, thanks for the kind words!

      I'm curious about your current role at Vox.

      I'm Design Director of Editorial Products, which just means I oversee the design team working on most of Vox's more intricate features and longform stories.

      What were the biggest challenges and most rewarding parts of transitioning to in-house work?

      Great question! The biggest challenge for me was just the sheer size of the company and the number of people. I'm horrible with remembering names, and all of a sudden there were so many more names to remember!

      The most rewarding part of it has been the same thing: the amount of people. I've been exposed to more people and viewpoints than I have probably since college, and I love it. I've really enjoyed learning from other and being able to share some of the stuff I've learned over the years too.

      And it's clear that you're still pushing great design and design vision forward; has working with the Vox team changed your perspective or your design process at all?

      I think if anything it's helped me refine it more. Or at least get a wider understanding of it. Also within a large group like ours, we can spend a little time specializing in some skills instead of one person needing to do everything. The collaborative side of the process gives me fresh eyes and inspiration for the work we do.

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  • Jens LukowskiJens Lukowski, 2 years ago

    Hi Jason. Thank you for doing this and your book On web typography. How did you learn about typography? And how did you learn to design? Any advice for someone new to it all?

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    • Jason Santa Maria, 2 years ago

      Hello, Jens!

      Thank you for doing this and your book On web typography.

      Thank you!

      How did you learn about typography? And how did you learn to design?

      I went to college for design and developed a love for typography from my classes there.

      Any advice for someone new to it all?

      If you have the option to attend school, I think it's a good idea. Learning amongst peers in a safe environment is immeasurably useful (you get to learn from your mistakes and successes, as well as everyone else's). Beyond that, there are many elective classes, conference, skillshares, and meetups where you can get a good introduction to design, and many won't require a large financial drain. Most important of all, read and practice. Immerse yourself in the world and just keep experimenting on your own.

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  • Brian DelaneyBrian Delaney, almost 2 years ago

    Hey Jason. Thanks for doing this.

    I'm curious about your thoughts on how interactions are shaping design. And how important is it that we develop a common language for these interactions?

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    • Jason Santa Maria, almost 2 years ago

      Thanks for having me, Brian.

      I'm curious about your thoughts on how interactions are shaping design.

      I think interactions are shaping design in really strange new ways. Before mobile devices, most interactions in design either dealt with physical moments (holding a book, flipping the pages) or virtual approximations of physical moments (clicking a mouse button to click a "button"). And even beyond that, the way your computer desktop was modeled after your desktop in real life.

      Obviously, these are really basic examples. But once we started to carry these small computers with accelerometers around in our pockets and bags, what constituted an interaction blew up! Just think of when your phone's compass loses it's bearings and you have to wave your hand around like you're doing an interpretive dance.

      What that amounts to is that interactions can now be anything and everything. A swipe on a screen, moving an object in physical space, just looking at something, and everything in between.

      And how important is it that we develop a common language for these interactions?

      The breadth of interactions we can design now, let alone what may come next, is staggering. As someone who loves guidelines, I know it makes me feel confused and worried at times. But I think all this exploration is healthy too. The experiments that stick become patterns, whether through documentation or just pack knowledge, and we build on them. Most of the stuff that does stick is usually a short hop from intuition anyway.

      So we can use and reinforce the patterns, but not so strictly that we can't leave ourselves some leeway to explore new ideas and develop new patterns.

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      • Brian DelaneyBrian Delaney, almost 2 years ago

        Thanks for the reply! I feel like we're going through some growing pains right now with mobile interactions. Confusion and worry has set in here as well. I'm looking forward to seeing which patterns stick.

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  • Yang MeyerYang Meyer, 2 years ago

    How do you and your design team collaborate with your developers?

    What is your workflow for getting assets from Photoshop/Sketch into the web/mobile project you’re working on? How do you track which ones need to be retouched?

    (Full disclosure: I am the maker behind Gemba, a Mac app for delivering assets into Git and Xcode.)

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    • Jason Santa MariaJason Santa Maria, almost 2 years ago

      How do you and your design team collaborate with your developers?

      We live in Slack these days because we're a distributed team. We're constantly talking and discussing projects, and a large part of our collaboration happens there. Beyond that, we often chat over hangouts and calls, or face to face when we can.

      What is your workflow for getting assets from Photoshop/Sketch into the web/mobile project you’re working on?

      I export them and then reference them in my code :)

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  • Kevin OhlssonKevin Ohlsson, 2 years ago

    Hey Jason, what's your opinion on working for free to build a portfolio?

    Peace

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    • Jason Santa Maria, 2 years ago

      If you are starting out, sometimes you need to do whatever it takes to build a portfolio. That doesn't mean you should offer to work for free, you should always try and get paid a fair wage, but you can consider doing some pro bono work. Whenever I've done this, I've often negotiated for greater creative control over the final product (money isn't the only thing you can negotiate).

      But another option to fleshing out a portfolio is to fabricate your own projects. You can looking for interesting design problems to tackle, or just create a project for yourself. Make some posters, devise a new company to make a logo for, and then make a website for it. There are many ways to exhibit your skills in your portfolio.

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  • Eric CozartEric Cozart, 2 years ago

    As far a smaller print design projects go.. what are some of the elements that interest you? What have you seen in regards to focusing reader attention on certain areas?

    Getting into print template design pretty heavily lately and in that, have noticed that one pagers are almost more difficult than multiple page design.

    Cheers and thanks for doing this!

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    • Jason Santa Maria, 2 years ago

      Thanks for the question, Eric!

      As far a smaller print design projects go.. what are some of the elements that interest you? What have you seen in regards to focusing reader attention on certain areas?

      I'm assuming you are asking more about direct mail or maybe promotional design. I don't do much of that these days, but I always enjoyed the constraints involved in those projects. For instance, the design constraints of designing a business card or post card. Just having a limited and known canvas gave the design edges (figuratively and literally), and put my mind in problem-solving mode.

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      • Eric CozartEric Cozart, 2 years ago

        Thanks for the reply. I was specifically talking about one page pdfs for proposals, lead magnets, marketing materials, smaller ebooks etc..

        I guess I just get lost at times in the smaller constraint. While I do love it, I think packing to much, or not enough, onto the page is a big challenge for me...

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  • John AnzelcJohn Anzelc, 2 years ago

    Hi Jason, I enjoyed reading On Web Typography. Is there anything you wanted to add in the book, but didn't quite fit? Was there anything about the process of writing the book that surprised you?

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    • Jason Santa Maria, 2 years ago

      Hi John, thanks for reading my book!

      Is there anything you wanted to add in the book, but didn't quite fit?

      Yes! I wanted to cover a lot more hands work for responsive design and how typography plays into that. I also cut out a larger section on icon fonts after realizing it was a little too tangential. There were other topics I wish I could've gotten to, but I imagine that's the way it always is writing a book.

      Was there anything about the process of writing the book that surprised you?

      Oh wow, how about all of it? :)

      I have written on my personal site and given presentation for years. My book itself was based on a talk I gave by the same name. I foolishly thought I could just sit down and write out the stuff I said in my talk and be half way to a book. I did that and it filled about 5 pages. Also, writing a book has a different kind of permanence (if there can be a thing) than writing online or speaking. Some of that might just be mental, but it was a considerably more detailed process for me.

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  • Jonathan ShariatJonathan Shariat, 2 years ago

    Any advice on seeking a place to work that is the most worth my time?

    Everyone keeps saying that its the same everywhere, but I refuse to believe that there aren't at least a few places with mutual respect, passion for what they do, opportunities to learn, be challenged, and an interesting problem.

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    • Jason Santa Maria, 2 years ago

      I hear you, Jonathan and can empathize. I've been in bad spots before and felt like there must be something better out there.

      Everyone is wrong; everywhere is different.

      There are jerks out there who don't know how to run a business. There are bosses and coworkers that are passive aggressive and will heap inane busy work on you.

      But that's definitely not everywhere. There are good place with healthy cultures. There are good bosses that trust you and let you explore. Sometimes you fall on your face, and sometimes you don't. They'll be there beside you either way.

      Just like in your personal life, there are also toxic ones that leave you feeling diminished and empty. But there are healthy relationships and friendships that nourish and challenge you to be the best you possible.

      Finding the latter is tough, and may not happen soon if you are first starting out. Often times, the only way I got to understand what healthy felt like was by first going through the unhealthy situation.

      My best advice is this: keep an open mind and try to be honest with yourself. You can learn from everyone (even the bad people, and that lesson might just be "avoid this person"). Ask friends for advice and a gut check. And above all else, don't sit back and feel like there isn't something good out there.

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  • Frank ChimeroFrank Chimero, 2 years ago

    Hi Jason. What makes a good cheesesteak? Are there any worth having outside Philly? Is it possible to make one at home?

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    • Michael AleoMichael Aleo, 2 years ago

      Damnit, Frank wins.

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    • Jason Santa Maria, 2 years ago (edited 2 years ago )

      What a good question! These are contentious questions, but I will offer my take:

      What makes a good cheesesteak?

      A long roll that's a little flakey and firm on the outside and a little soft on the inside (preferably Amoroso's), thinly sliced or chopped steak (usually ribeye, and I prefer chopped), melted cheese (american, whiz, even provolone), wit (fried onions), and a Philadelphia zipcode.

      Are there any worth having outside Philly?

      Some friends helped me find a few in NY after my stomach got homesick. 99 Miles to Philly is the real deal. Oddly, you don't even have to get far away from Philly before the quality drops precipitously. Maybe it's something in the water.

      Is it possible to make one at home?

      Yes! Though it's tough. When I was little, my family would make them at home sometimes and I grew to like them. But you really need a huge flat top grill.

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  • Axel ValdezAxel Valdez, 2 years ago

    Hi Jason, it's an honor, I'm a big fan.

    1. Do you manage to disconnect from work sometimes? If so, How do you do it?

    2. Do you think that we have lost something over the years, comparing today with the days of fighting for web standards?

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    • Jason Santa Maria, 2 years ago

      Thanks very much, Axel!

      Do you manage to disconnect from work sometimes? If so, How do you do it?

      Yes, often! It sounds dumb, but it works: I schedule down time or time to just dedicate to something else. All of my work goes on my calendar and has time reserved for it, so why can't I reserve time for other things in life.

      Do you think that we have lost something over the years, comparing today with the days of fighting for web standards?

      Definitely not. I know I'm guilty of looking back on those days and romanticizing some of that stuff (everything was small and you knew everybody!), but designing and being able to flesh out ideas is so much better now. And wow, is that better for everyone looking at our sites. No weird site versions for one browser or another; now we just make a website.

      The fact that our industry exploded with people means we probably got something right :)

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  • Michael AleoMichael Aleo, 2 years ago

    Hey Jason, I've thanked you before for reinvigorating my design career with your talk at AEA in 2007. That talk completely changed my outlook on things.

    Are you still doing a lot of client work, or are you spreading your focus among a bunch of different stuff these days (single products, education, A Book Apart, etc)? Do you ever miss the craziness of agency life?

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    • Jason Santa Maria, 2 years ago

      Wow, thank you Michael!

      Are you still doing a lot of client work, or are you spreading your focus among a bunch of different stuff these days (single products, education, A Book Apart, etc)?

      Last year I took a position at Vox Media. It's the first time in over a decade I've been at a full time job (at least where that wasn't because I helped start the company). It's been a huge change for me, but a much needed one. I was getting a bit burnt out from client work and losing my love for it.

      Do you ever miss the craziness of agency life?

      Not really. I didn't think I'd ever say that, but I'm glad I can now. It was always about just being part of a team and getting to collaborate with smart people. As long as I can do that, I don't mind being at an agency, startup, or in-house.

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  • Kelly SuttonKelly Sutton, 2 years ago

    Hi Jason,

    Thanks for being with us today. You have worked quite a bit on authoring platforms to date, and I think they are fascinating pieces of technology. (There’s a joke out there that every publisher is doomed to reinvent the CMS.) Thus, my questions are around those.

    • How do you feel about the current state of authoring platforms online?
    • Do you see professional and personal platforms converging or diverging?
    • How does the design of these internal interfaces distinguish different platforms? How could they do a better job at that?
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    • Jason Santa Maria, 2 years ago

      Thanks for having me, Kelly! These are some involved questions, but I'll try to unpack them a bit:

      How do you feel about the current state of authoring platforms online?

      On the whole, platforms online feel great from a UX perspective. The ease with which we can publish and share is fantastic, and the ability to achieve a good baseline of design while doing so make me happy as hell. For instance, the work that Marcin Wichary is doing over at Medium to enable solid typography by default.

      I worry a little about the move away from personal sites for publishing stories. Not because I lament people not writing on their sites (I do), but because I don't like moving all our writing into central publishing systems that may not have everyone's best interests in mind.

      Do you see professional and personal platforms converging or diverging?

      They've very quickly become one in the same. WIRED just relaunched and doubled down on WordPress, Medium has both personal stories and full blown publications now. I think the personal divide exists much more prevalently on mobile app platforms.

      How does the design of these internal interfaces distinguish different platforms? How could they do a better job at that?

      I can't speak for all platforms, but the nature of the UI will always steer the kinds of interactions you can have there. We can always do a better job at that. We've gotten the publishing part pretty well nailed by now; if you want to write something and get it online, the barrier to do so is small. I'm much more interested in helping people craft the way they tell their stories. If we just drop different kinds of content into the same design, we're not doing a great job as designers or storytellers. Design should be able to respond and support writing, and that starts with the interaction around writing.

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