Jason Santa Maria

Jason Santa Maria is the co-founder and creative director of the collaborative writing platform Editorially; a faculty member in the MFA Interaction Design program at SVA; a co-founder of A Book Apart; and the founder of Typedia, a shared encyclopedia of typefaces online. Previously, he served as vice president of AIGA/NY and as creative director for A List Apart and Typekit. He's worked for clients such as AIGA, The Chicago Tribune, Housing Works, Miramax Films, The New York Stock Exchange, PBS, The United Nations, and WordPress, with a focus on designing websites that balance beauty and usability. He discusses design on his award-winning website.

Jason has a Twitter account, too. Follow him @jasonsantamaria

Published Thoughts

I register a lot of domain names. Chances are if you’re reading this, you probably have at least a few yourself. Only a handful of mine are in active use. All the others represent a good intention I had to make an awesome website.

The domains all start innocently enough: it could be a funny turn of phrase I hear while out with some friends; an overheard quip from a television in background; a little burning ember of an idea that keeps coming back to me. There was the one where I would interview people about their most prized possession, or the single-serving site about alternatives to using Helvetica. The list goes on and on.

Around this time of year a bunch of my domain names come up for renewal—likely registered after nights out with friends around the holidays. When they came up for renewal this time, I had to stop and think for a minute. What the hell am I doing? Why do I keep renewing these domains when I will probably never get around to doing anything with them.

This is a domain affliction. It feels encoded in any of us working on the web; we register domains at the drop of a hat. Not because we’re looking for a future pay day, but because we’re in constant conflict with the evil domain squatters.

In recent years, the internet has self-corrected the domain squatter problem. There are many viable TLDs available beyond the workhorse .com, from .co, .io, .is, .me, and so many more. But the big change here is that URLs just aren’t that important anymore. It’s still nice to have a short and memorable domain, but the means to get to a site is more important than ever: links. It doesn’t matter how long or weird your URL is, just link someone to it.

Maybe it’s time I got rid of those extra domains.

Years ago I mused that it would be fun to hold a poker game and use domains as the chips. Though, that could actually mean walking away with more domains than you arrived with. Ugh!

More recently I thought it could be fun to have a site (hey, I could get another domain!) where people could list domains for others to claim. But with a catch to keep the domain from just languishing on someone else’s shelf: they’d have a month or so to make a site that uses the domain before it would be transferred to them.

But that seems silly too. Almost like instead of collecting domains I’m collecting ideas to offload domains. Honestly, if I haven't followed through on the idea behind a domain by now, I'm just wasting money on them. Money that could be going to a charity or at the very least, not down the drain. And some non-domain-squatter might have a better idea for that domain anyway.

I think as my unused domains come up for renewal I’m just going to let them go, or offer them to folks who might use them. There was a time when a domain represented a placeholder for an idea to me. And worse yet, buying the domain gave me a feeling of accomplishment that took the pressure off of having to finish anything more. Now they’ve just become a neglected to-do list (and I have some of those too).

If all those domains went away tomorrow, I would still have the ideas. Those creative impulses can be just a list or a scribble in a sketchbook, until they actually need to be something more. There will be plenty of domains.

I often talk about how sketching is an important step in making something. Whether with pencil and paper, or a keyboard, generating ideas is essential. I struggled with this early on in my career because I felt like putting something down on paper gave it a permanence greater than its value. I thought that by recording something, I was accepting ownership and responsibility for ideas I wasn't sure of.

Over time, I came to realize that the only way to get to the good ideas was to trudge through all the obvious and bad ones first. Don't get me wrong: flashes of inspiration happen, but ideas rarely pop out of your head fully formed and ready to go to work. More times that not, ideas are ugly, raw, embarrassing things that you want to slink away from. Most of my ideas never leave this stage.

I want a big sprawling mass of ugly ideas because it helps get past the most obvious ones, and improves the chance for something really interesting to reveal itself. Because the real shape of an idea isn’t an explosion, but evolution. In order for an idea to become something valuable, it needs to be nurtured. It must be molded and fortified into the best version of itself. And that refinement is where our creativity shines. Our ability to combine and link ideas to make them stronger. One small idea opens the door to another. And once you can see that new pathway, it too opens the door to another idea that wasn't visible from the start.

After 36 years of life, I finally get why people run. I mean, I always understood why people were running in the park or down the street, but this understanding was coupled with internal mockery. “That seems like a painful way to spend time.”

My mockery was probably more jealousy than malice. I grew up as a short and scrawny kid, and I loved to run. I was always running—but only for short distances. I only wanted to get from point A to point B quickly, and only if point A and point B weren’t too far from one another. Even when I ran track in school, I was built for sprinting, but distances eluded me.

Something changed recently. One day I woke up and decided to go run in the park like all those other people. I wouldn’t go to the gym that day, I would enjoy the outdoors and run.

I ran a lap around the park, walked a half lap, and repeated a few times. This equalled out to about three miles total. I felt like absolute death. I was panting and gasping, and long dormant muscles screamed out in pain. I got home and didn’t work out for the rest of the week because it hurt to move my legs.

But here’s the thing. The next day, even as I was groaning in pain, all I could think about was the next time I would be able to run again. And I totally did it again. The next time it didn’t hurt so much. And the time after that it didn’t hurt at all and I ran even farther.

I know this story isn’t going to come as a surprise to any runners out there. But this was huge for me. I love the outdoors, and I love any kind of exercise that doesn’t have me looking at a digital distance counter every two seconds so I can mentally determine when I’m allowed to stop moving.

I’ve been running regularly for well over a month now. I wouldn’t say that any fraction of a marathon is in my future, but somehow distances don’t feel as unsurmountable as they used to.

Maybe I found out how to make running work for me, or maybe I just never really gave it a good honest try. Whatever the case, I absolutely love the times I get to run in our park. I love feeling the little aches in my muscles for the rest of the day, and knowing that my body is alive. It took me over three decades, but I get it now. I get why we run.

This month I want to share a letter I received from ex-designer, now sheep farmer, Ruth, in reply to my post from a few months back where I wondered what comes next after being a designer. Ruth kindly shared where her life led, and what the other side might look like. I was moved by what she wrote, not only because of her direct experience, but just to hear that I wasn’t alone with my own fears about exhuastion and nourishment.

One letter happily turned into numerous replies back and forth. Ruth graciously gave me permission to share our correspondence, in the hopes that it might also provide comfort and insight others.

Hello Jason, I just completed reading your article “What’s next”.

Just to let you know — there is life, beyond design, though you never quite let it go 100%.

When I went to college to learn design and print, I learned hand setting, then on to Linotype / Monotype machines. My first job, out of college and they were introducing film set typography (Berthold machines) — learning curve again. A number of years later and I was running my own design business and along came… computers and that was an exceptionally steep, self taught learning curve. In order to keep up with the ever changing technology you do have to learn and that takes motivation and desire from an individual point of view.

I enjoyed that “learning” — but what did it for me in the end — “repetitiveness” — my ability to “train” my client became a drain — each client seemed to require, at some point, the same explanations of what was and was not possible with the technology available at the time. It became so draining I called it a day.

I am now a sheep farmer in the northern Highlands of Scotland — and this has also been a challenge of a very different kind — man against nature — but, I have enthusiasm, motivation and a desire to learn something new, something “different”. But — yes, I keep learning about design — web design, which was in its infancy as I was leaving the design field 15 years ago.

What’s next — all depends on you, what motivates you and what makes you happy — there will always be new challenges, but that is what life is all about, isn’t it.

Kind regards
Ruth (now 60 years old — lol)

Ruth’s note warmed me, and after some exchanges, we got onto the topic of exhaustion. I replied back with my personal thoughts on the matter:

Hi Ruth,

The main things I keep coming back to are primarily about exhaustion. I used to think I was working too hard, but even as I found ways to work less, I realized it was something else. I think my exhaustion comes from the industry often taking more from us than it gives, and I’ve only found this to be escalating with how disconnected we’ve become, even in the midst of things like Twitter. Everything feels just a bit thinner than it used to, or at least a bit less nourishing. But when I throw myself in another direction, whether reading, or teaching, or other crafts, I feel nourished again. I’m still working through my own thoughts, and don’t mean to sound so dour about the practice of design, but I think just being aware of what feels good for my mind versus what doesn’t, makes me feel better.


Ruth’s reply was spot on again. Particularly insightful to me, and something I try to continually remind myself of, the expectations of others are their own, and I don’t need to share them:

Hi Jason,

Ah — yes — exhaustion — equates to my being “tired” of the industry — I fully understand where you are coming from.

I found the move to computers a difficult one — I was so familiar / used to working at a drawing board and creating with my own hands — using a mouse and creating on screen was a tough hurdle. Once I overcame that I began to see new possibilities and regained some excitement — however, that was relatively short-lived. As with many things in life — with advantages, came the disadvantages — time scales and demands / expectations of clients. Time scales got shorter — where once, it took 4-5 people a month to put the artwork together for a 1k page book — it became 1 person in a week. I suddenly found I was getting nothing in return — sure, I was paid, but that, somehow, just was not enough. I had the “trappings” — nice home, super sports car and had the ability to fly off to Colorado for long weekends. But it did nothing to fill a gap that had somehow arisen. I took up wood turning — something “creative” I could do with my hands, but even that never quite made up for my working day.

When “new technology” arrives on our doorstep, we do work hard, very hard, to learn it well. I remember being taught to use a ruling pen in college (pre rotrings) and that was so hard to master — my lecturer stated — a designer must master their “tools”. I did that all my working life in design — from hot metal, to film setting to full computerisation — but the “craft” and the mental reward diminished.

I tried “twitter” in it’s early days — but I felt disconnected, did I really want to know if someone was at an airport waiting to fly to XXX — most posts from people seemed utterly irrelevant, so I gave up. Okay, so I am on facebook (reluctantly) — but that is a way of keeping in touch with my brother, sister and their families.

I do believe you are working out, by trying to throw yourself into different things (teaching, reading, writing) — just what is missing. Eventually, something will click into place for you. Just try to remember, no one expects you, as a person, to remain “static” — to always do the same thing, day in, day out — that can lead to stagnation, not just for ideas but for you as a person. I am absolutely NOT advocating that you go do something as dramatic as I did — from designer to sheep farmer (though that was accidental, they were just a way to keep 40 acres of grass down). Also, perhaps try to remember no one has expectations of you — but you have to have some “reward” for your efforts — and I don’t simply mean monetary.

Keep working on it — it is important to you, in your own personal development — that development is important — not the expectations of anyone else. Self-worth is so important.


Thank you, Ruth. I greatly appreciate you taking the time to share your experience with me. It has already served as inspiration for whatever comes next.

A large kitchen in your average New York apartment is like a mythical beast. You may muse about their existence from time to time, but chances run high that they aren’t real things. Many kitchens in one-bedroom apartments here are little more than the wall of a non-kitchen room that happens to have some appliances leaning against it. Your living room is usually reserved first for a couch, and space permitting, a table or closet (closets are a whole other thing).

Having a dining table in New York is a luxury. My first apartment here was big enough to hold a small table which I could sit at comfortably, and another person could join me at uncomfortably. A few years later, I moved to another apartment that was the same size, but differently laid out. This apartment had a huge kitchen with space for many people to occupy simultaneously.

This new kitchen of mine took up nearly a third of the apartment’s footage and was big enough for a proper table. I knew right off I wanted a big farm table — something solid and uncomplicated.

After looking around for a long time trying to find the right balance of form vs price, I became discouraged because big tables are pretty expensive everywhere (who knew?), and settled on one I found on eBay. I say “settled” because I thought “I’ll get this table now, but then buy a really nice one when I can afford it.”

The table was made of unfinished pine from an Amish furniture maker in Pennsylvania and an irregular castoff he was selling at a discount. I couldn’t detect any problematic irregularities from the pictures — these tables should probably have some rough edges anyway—so I bought it.

For the first year I owned the table, I casually regarded it as a thing I planned to replace, so I didn’t put much work into it. It’s a hulk of a thing, with corners that come justthisclose to achieving right angles. I tried sanding its rough legs a few times and was rewarded with some of the biggest splinters I’ve ever encountered in my life. I didn’t take the table makers’ advice to oil the wood, so on cool nights I was sometimes woken by terrifyingly loud pops that I later discovered were the table boards splitting.

I chalked all that up to the table having some character. Later my partner Megan moved in, who sensibly got us to wax and oil the table. Gone were the pale boards and in their place stood a downright healthy looking table, albeit prematurely weathered due to negligence.

We have guests over for a meal most every week, and every week we’d gather around that table. Sometimes the gatherings are jovial events that stretch long into the night. Sometimes they are somber times shared over quiet dinners. Amid broken glasses, spilled drinks, dirt, and countless food items, that stubborn table has stood strong.

I used to think about the table I would get to replace this one. I would often tell people it was a temporary occupant. But now I look at that table and all I can see are the times we’ve spent gathered around it. All the meals and wine, the conversations and laughter, the tears and embraces. This table is full of memories and times spent together. It’s imbued with so much personal history that it’s a part of the family now. I don’t see its surface faults anymore, I just see myself and my loved ones. I wouldn’t trade this table for anything now.

I’ve enjoyed contributing here on the Pastry Box this year, if for nothing else than it’s gotten me writing on the regular again. Having a deadline helps drive it into my skull repeatedly that writing has less to do with skill, and more to do with showing up. Making the clackity noise really does work. Just like merely putting pencil to paper counts as sketching. I should know this by heart by now, but I’ve come to the conclusion that I’ll need life-long reminding.

Each month when I feel my Pastry Box deadline approach, I set my mind to sponge-mode in case an idea happens to present itself. I start jotting down notes on paper, in random text files, and peck out sentences in emails to myself while I ride the subway each day. Few of these ever get used for anything, but they all resonated with me in some way when I wrote them.

Over time, I’ve amassed a considerable amount of drafts and unorganized thoughts. Some date back to when I first started blogging (we were really preoccupied with IE6 back then) and the pile since then keeps growing. When I can’t think of anything to write about, I often go back and skim through these drafts to see if there is a loose thread I can pick up. There are many thoughts that were interesting to me for a time, but it rarely happens that one might strike me now. If these thoughts resonated with me before, why can’t they now?

I used to feel like a bit of a failure when I would look back on all these drafts and see them as uncompleted work. Perhaps these ideas are just sketches in their own right. Not exact, not refined, just ideas in their preferred state: ugly. They have a lot of raw gumption, but few have a leg to stand on. Without planning it, my writing process turned out pretty similar my sketching process.

I often think about that maxim of “strong opinions, weakly held”, and it really rings true to me. I love imagining many different scenarios when I sketch or write—and even when I form an opinion—I invariably end up having my mind changed down the road.

The drafts I have aren’t incomplete works anymore, they’re old points of view that have changed. I haven’t picked up some of those threads because I probably don’t agree with them anymore. Making the clackity noise or scribbling in a sketchbook are just ways of trying ideas on for size. If they don’t fit, that’s alright, I can cast them aside. And that’s kind of the point anyway. Good ideas have a way to coming up again, begging to be nurtured and finished.

I’ve noticed something interesting happening in editorial design online. More articles, and websites in general, are focusing on slowing down to not only convey their story, but to set and maintain a mood for the reader. There are many ways to do this through the writing itself, but I wanted to take a moment to point out a way that design does this through small interludes.

To see what I mean, check out this story from Matter: This is what it’s like to be at war with your body.

It’s a well considered article design-wise, lots of nice typography and whitespace for starters, but look at the bits between the text. Sometimes it’s a large and exaggerated drop cap, a big photograph, or a splash or color, but look even closer. These elements share a visual language of size, color, and placement. Now look at the drop caps. They are trimmed asymmetrically, a visual reference to the subject of this story: voluntary amputation and body integrity identity disorder.

It’s a small detail, but it does a big thing. That little treatment, the photos, colors, big type, and pull quotes are all used to maintain a mood. They pop up at intervals to check in on the reader, and to keep the story moving. They function almost like the chorus of a song, maintaining a thread to a story, sometimes alluding to where you’ve been, where you’re going, or to punctuate a point in the journey.

It’s a technique that’s been popping up in a lot of places, but doesn’t often get scrutinized. I imagine it usually gets lumped into the idea of “longform” writing or art direction, but we don’t often talk about how much heavy lifting this little technique is doing.

Similar interludes are used to great effect in other mediums like film, music, and radio. Every week when I listen to This American Life or Radiolab, I know that the pauses between segments where the music volume rises are there for a reason: they support the story by keeping me in a particular mental space. These occurrences aren’t happenstance, they’re meticulously planned, and are in direct service of the listener. They give us a moment to reflect on the story so far and prepare for what’s next. They replenish a mood over and over again, so that we can continue along with that experience and feeling a certain thing.

Seeing this kind of consideration for storytelling on the web is a serious about face. Not because writers and designers haven’t cared about storytelling, but because we may be past the point where they could still be successful despite not caring. Offhandedly dumping text into a column on a webpage used to pass for an article, but the existence of a website isn’t novel by itself anymore.

Maybe folks on the web have grown more sophisticated. Maybe there is just too much out there to sift through and small considerations like this help us find the meat. I’m happy as a designer, and as a reader, to see more people taking the time to build things striving for greater significance.

Frank Chimero’s transcripts of some of his recent presentations, What Screens Want and Designing in the Borderlands, are an exceptional example, translated from one medium to another. The New York Times garnered lots of attention with Snowfall a couple years back, but they’ve continued investing in excellent longform and interactive storytelling. Organizations like ESPN and Vox Media have been up to the same even longer and continue to push out interesting reporting. And still more folks like Victory Journal and NPR are exploring the possibilities of reporting beyond only the written word.

Consideration for communication takes effort. It’s more than just the addition of some music or moving pictures, it’s a recognition of a broader story being told. Something bigger than text casually abandoned in the corral of a webpage. It’s the acknowledgement that a story can happen in multiple dimensions, across time, sound, and image. Our stories have an ebb and flow, and design serves to support and enrich them.

In the back of my head is always a thought: What will I do when I stop designing websites?

It’s not because I want to stop—I love what I do—it’s that I wonder how long I can expect to do it. I don’t think it’s unrealistic to think that there will be a time when I don’t want to, or can’t—due to fatigue or professional obsolescence—work in this industry anymore. It may not happen, but planning for that possibility isn’t a bad idea either.

I think about this stuff because the speed of life and our industry can be humbling and terrifying all at once. It’s not just about keeping up with the latest techniques or news, but also finding time to continue developing the skills you have. There’s never really an end point to learning, just different plateaus of understanding.

Not long ago I was having a conversation with a friend who wondered if web designers might go the way of typesetters. Type used to be painstakingly set by hand, letter by letter. But that laborious process, as well as the skill involved, was subsumed by faster typesetting technologies like the Linotype machines. Later still, most Linotype operators were made redundant by computers. Advancements and displacement aren’t new things—I’m sure there was a time that scribes using clay tablets shook their fists at those snooty papyrus jerks—but it’s a cyclical thing.

With so much money flying around for valuations and acquisitions every week, no one would fault you for thinking our industry isn’t a stable one. Whatever ways things change, being mindful that they will change is a smart perspective, lest we all become today’s Luddites.

The stories we tell of the drive of faster automation and industrialization are cautionary tales, not because of the rise of machines, but because of our own stubbornness. Like many designers, I’m also afflicted with the fetishization of past parallels for what I do now. I love books and manually set typography—the byproduct of hard labor with one’s own hands to produce something unique and beautiful. But I also delight in how much more is possible for communication and connection with today’s tools.

I’m not entirely sure what options I would have if I wasn’t a designer. There are certainly themes throughout most everything I’ve done so far in life. Art. Drawing. Color. Type. Rhythm. I’ve invested so much time and energy into doing this, and the drive I had in my youth certainly made things easier. I have that same drive now, but sometimes it’s feels like it’s shifted towards deeper understanding rather than broad learning. I like getting further into the details of topics. And that’s when I get scared that I’ll get caught unawares by progress, like a twisted game of musical chairs.

Standing with one foot in the past and one in the future is a good thing. It honors those that came before and their work, but also incorporates progress. Maybe the key is not getting caught flat-footed when the future makes a shift. Flexibility in work habits and in thinking, rather than languages and programs, might be our most useful skills.

My grandfather was a carpenter. He built many houses, including his and my grandmother’s, and my family’s home. He always had a pickup truck because that was his means to signal to the world that he was in business. Even after he had retired, he insisted on having a pickup truck so that he would always have the option to work if he needed it. That was a door he never wanted to close.

His friends and coworkers would meet at a local diner every morning for breakfast and to have a few laughs. I remember passing the diner on my morning school bus ride and seeing his and his friends’ pickup trucks lined up in the parking lot. They all had trucks too because this was how they told the world, and one another, that they were working.

I admire my grandfather for a great many things, but most for teaching me about craft and good day’s work. He could swing a hammer and liked making things with his hands, and until the end, wanted to be perceived as someone who could so. That was essential to him because he identified himself by the things he made.

And he made good on that. After retirement, he built a few more houses, including my family’s. He let me help with that one, and though I was only six, I tell myself the tangle of boards I nailed together in an adjacent pile of dirt were totally load-bearing. He taught me how to swing a hammer and how important it was to level your work and measure twice.

His truck, his hammer, his group of friends, all meant he was on the job. And most importantly, that he always had the potential to make something.

When I want to find out more about my own work, I ask a question. When someone asks me to look at their work, I ask a question. It’s a silly thing to say, but it took me years to do that. 

It’s silly because it’s probably obvious to you, or to anyone who’s thought about it for a moment: If you want to get a better understanding of something, asking a question is infinitely more useful than making a statement. 

It took me years to get there because I fell into the same trap many young designers do when in a critique—I tried to participate by offering answers. 

Answers are appealing, of course, as is the idea of a charismatic leader who has pockets full of them. But of all the work I’ve done, the projects I consider most successful were accomplished by teamwork. Answers shouldn’t come from one single person, no matter how skilled they may be. Instead, they come as a result of discussion among peers. 

Asking questions is at the heart of collaboration, more so than any project management software or process. And if you want to truly collaborate, I’ve found you need to allow yourself to be someone without the answers. 

Have you ever seen something that someone else made that you just hated? What happened next? Did you rush to Facebook or Twitter to share your disdain with the world?

I know I have.

See, I try to live as a kind and considerate person—so I hate to admit that I have that side to me. And it’s probably always been there. But in the pre-Internet past, it would have only manifested as some silent quips to myself in my head.

I want to be a better person and, just as importantly, I want to be a better member of our community. And I want you to be, too.

So here’s my advice to both of us—to you, and to me: let’s take a breath.

Our pithy remarks can wait at least that long. What’s more, that time might give us a chance to reconsider posting something negative about someone personally or their work just because we weren’t consulted. In other words: let’s not just react. Instead, let’s take a moment to try to understand what’s in front of us, before we speak up. There’s a reason we don’t ask people to create an opinion. We ask them to form an opinion, because that formation takes time and consideration.

An immediate thought that pops into our heads when we first see something is rarely considered, full formed, or hell, even what we really think. It’s often just a reaction to stimuli. That stimulus doesn’t require us to reply with an opinion. Oddly enough, none of us actually need to have an opinion on every occurrence, and certainly not a knee-jerk reaction masquerading as a thoughtful point of view. The Internet has already reached peak snark.

What’s more, critique is not synonymous with “being mean.” It’s not an opportunity to show how smart you are. Thoughtful feedback doesn’t include the words “meh” and “fail,” or begin with “Isn’t in ironic that....”

Critique is about growing. As Leah Reich so thoughtfully wrote in The Uncanny Valley of Earnestness:

Criticism is not negativity. Criticism is not saying you’re bad. Criticism is – it should be – a way of saying: I think you’re good. I know you can do better. I think you can figure out a way how.

I wonder if the speed and accessibility of our social tools can sometimes make us aggressive, even antisocial. Maybe we’re forgetting there are people behind those avatars and usernames. People who work hard and care deeply about what they do. People like you and like me. And as we all know, we’re rarely working under ideal conditions, timelines, or constraints.

The worst part is that this low-level snark falls between the couch cushions of Wheaton’s Law. Most of us aren’t dicks. Most of us aren’t trolls. But there are times when any of us can be sloppy, impatient, or distracted communicators. An inadequate venue for critique, whether in person or in 140 characters, only makes things worse.

There is plenty of room for strong words and tough love in critique, but never for insult or snark. There is a time to appreciate or bemoan work, but it’s usually not the moment just after you’re first exposed to something.

We’ve all probably heard the phrase “haters gonna hate.” We console ourselves and each other with it when the tide turns against us. We wear it like a badge of courage because, well, what’s the alternative? I wish we could throw as much support into an opposite movement. We speak up loudly when we dislike something but don’t always say enough when we love something.

A measure I often use for myself when reflecting on any given day is: did I put more positivity into the world today than negativity?

So, let’s take a breath. And let’s spend a bit more time making well-formed thoughts before speaking our mind. We’re all doing our best out here.

Revised and adapted from my presentation during CreativeMornings’ 5th Birthday celebration.

Back in 2007, Speak Up—the web’s town hall for graphic design—asked where were the landmark achievements in web design. Where were web’s design equivalents to Milton Glaser’s Dylan poster, Paula Scher’s Public Theater work, or Massimo Vignelli’s New York subway map?

At the time I felt outrage. Were these graphic designers really throwing the whole of web design on a heap? Did people really not consider what we made real design?

What about Doug Bowman’s monumental work on 2002’s WIRED.com redesign, one of the first sites that showed us all that Web Standards and CSS could happen on something beyond our personal sites? How about Joshua Davis’ Praystation, who revealed complex animated interactions to a static web? Or communities like k10k that helped spread the message of good design and culture to all us practitioners?

None of these fit easily into the mold of a beautifully typeset poster on the side of a building, but these were more than websites or landmarks, they were full blown movements! Why couldn’t they see that?

I didn’t say anything about it at the time because I never felt I could articulate a response—the answers seemed apparent to me. The thoughts never went away, but I opted to just keep trying to make the best work I was able.

A recent tweet from Mark Boulton brought it all back again: “Graphic Design had Emigré. What does web design have?”

Of course! Emigré was the periodical for design culture and discourse. I read it religiously when I was in school and afterwards. The essays they published helped shape the way I thought about design. That kind of critical discourse about design on the web is all but non-existent.

We talk all the time on our personal and periodical sites about the latest techniques for design, but how often do we break down new designs? I mean really discuss them, not just add them to a gallery of notable sites.

Aesthetics are just one lens we can use to look at web design. Culture, time, place, and technology are others. Some websites look and act the way they do because of the state of technology during the time they were made. The landscape of architecture was changed by the invention of steel, just as the landscape of web was change by Flash, CSS, mobile phones, and Retina screens.

What’s more, graphic design critics and teachers constantly use these past landmarks to bring context to history, today’s design, and as a common measuring stick for what’s successful. On the web, we commonly move on to the newest things that displace what came before.

If work like Bowman’s WIRED.com website was so wonderful, does the fact that it isn’t suited to today’s web diminish that fact? We can build websites faster and smarter than we used to, they can respond to being viewed on screens as small as our mobile phone or as large as our televisions, but the work we do today is important for another reason.

We are all standing on the shoulders of the work that came before us—just as Vignelli’s subway poster was influenced by Henry Beck’s 1933 London Underground map, and Glaser’s Dylan poster was influenced by a 1957 self-portrait from Marcel Duchamp. Will new students to web design know of these same connections in their own field, or will the work done before their time always be quaint artifacts of a bizarre, retro internet where aliased type, tables, browser plugins, and slow connections ruled the land? Or worse, will they never know of the work at all?

If we are only able to judge web design through the lens of print design, we’re doomed to never measure up. Web designers know our work has very different parameters and constraints than the printed page. Even though we use many of the same raw materials—imagery, text, color, and grids—the results are very different. Why would you ever judge a website on the same scale as a poster?

A website is its own, singular thing. We know it isn’t a book, a TV show, a film, or a song, but our language is limited to talking about it in those restrictive boxes. A website is a mix of all of those things, and none of those things. It is influenced by place and time. A website changes with age. It can evolve and regress.

It was then I wondered if the problem wasn’t that web design lacked its own Emigré. What if we actually lacked a shared language to critically discuss web design? Art, architecture, and even graphic design, have critics and historians that give context to new work through the lenses of culture and important work from the past.

So where does a common language for discourse start? Not just one for us as web designers, but one that will give structure to others who don’t as deeply understand what we do?

The recent redesign of The New York Times perfectly illustrates the mindset of modern web design. The design itself is exceptional: solid typography, navigation, and further reinforcement to the visual language that makes The Times, well, The Times. While the general response has been positive, it’s bundled with some disappointment that the site didn’t innovate like “Snow Fall” or disrupt some paradigms.

The problem isn’t with The Times. In the last couple years, the site and their editorial design work has been brilliant. The problem is that we don’t have the right words to talk about this stuff, let alone the right context to find common ground for real discussion inside our industry or the folks just outside it. If our eyes are only attuned to the latest shiny thing, we can’t possibly understand anything of influence or consequence.

I realize I’m asking lots of questions, and I still don’t have the answers. I’m not a historian or a critic, I’m a practitioner. And perhaps that’s the key: maybe this needs to come from the outside, from people who can step back, see a larger picture of web design, and understand how it fits into everything else.