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Humility, a designer’s essential value—that has a nice ring to it. What about humility, an office manager’s essential value? Or a dentist’s? Or a librarian’s? They all sound great. When humility is our guiding light, the path is always open for fulfillment, evolution, connection, and engagement. In this chapter, we’re going to talk about why.

That said, this is a book for designers, and to that end, I’d like to start with a story—well, a journey, really. It’s a personal one, and I’m going to make myself a bit vulnerable along the way. I call it:

The Tale of Justin’s Preposterous Pate

When I was coming out of art school, a long-haired, goateed neophyte, print was a known quantity to me; design on the web, however, was rife with complexities to navigate and discover, a problem to be solved. Though I had been formally trained in graphic design, typography, and layout, what fascinated me was how these traditional skills might be applied to a fledgling digital landscape. This theme would ultimately shape the rest of my career.

So rather than graduate and go into print like many of my friends, I devoured HTML and JavaScript books into the wee hours of the morning and taught myself how to code during my senior year. I wanted—nay, needed—to better understand the underlying implications of what my design decisions would mean once rendered in a browser.

The late ’90s and early 2000s were the so-called “Wild West” of web design. Designers at the time were all figuring out how to apply design and visual communication to the digital landscape. What were the rules? How could we break them and still engage, entertain, and convey information? At a more macro level, how could my values, inclusive of humility, respect, and connection, align in tandem with that? I was hungry to find out.

Though I’m talking about a different era, those are timeless considerations between non-career interactions and the world of design. What are your core passions, or values, that transcend medium? It’s essentially the same concept we discussed earlier on the direct parallels between what fulfills you, agnostic of the tangible or digital realms; the core themes are all the same.

First within tables, animated GIFs, Flash, then with Web Standards, divs, and CSS, there was personality, raw unbridled creativity, and unique means of presentment that often defied any semblance of a visible grid. Splash screens and “browser requirement” pages aplenty. Usability and accessibility were typically victims of such a creation, but such paramount facets of any digital design were largely (and, in hindsight, unfairly) disregarded at the expense of experimentation.

For example, this iteration of my personal portfolio site (“the pseudoroom”) from that era was experimental, if not a bit heavy- handed, in the visual communication of the concept of a living sketchbook. Very skeuomorphic. I collaborated with fellow designer and dear friend Marc Clancy (now a co-founder of the creative project organizing app Milanote) on this one, where we’d first sketch and then pass a Photoshop file back and forth to trick things out and play with varied user interactions. Then, I’d break it down and code it into a digital layout.

Along with design folio pieces, the site also offered free downloads for Mac OS customizations: desktop wallpapers that were effectively design experimentation, custom-designed typefaces, and desktop icons.

From around the same time, GUI Galaxy was a design, pixel art, and Mac-centric news portal some graphic designer friends and I conceived, designed, developed, and deployed.

Design news portals were incredibly popular during this period, featuring (what would now be considered) Tweet-size, small-format snippets of pertinent news from the categories I previously mentioned. If you took Twitter, curated it to a few categories, and wrapped it in a custom-branded experience, you’d have a design news portal from the late 90s / early 2000s.

We as designers had evolved and created a bandwidth-sensitive, web standards award-winning, much more accessibility-conscious website. Still ripe with experimentation, yet more mindful of equitable engagement. You can see a couple of content panes here, noting general news (tech, design) and Mac-centric news below. We also offered many of the custom downloads I cited before as present on my folio site but branded and themed to GUI Galaxy.

The site’s backbone was a homegrown CMS, with the presentation layer consisting of global design + illustration + news author collaboration. And the collaboration effort here, in addition to experimentation on a ‘brand’ and content delivery, was hitting my core. We were designing something bigger than any single one of us and connecting with a global audience.

Collaboration and connection transcend medium in their impact, immensely fulfilling me as a designer.

Now, why am I taking you down this trip of design memory lane? Two reasons.

First, there’s a reason for the nostalgia for that design era (the “Wild West” era, as I called it earlier): the inherent exploration, personality, and creativity that saturated many design portals and personal portfolio sites. Ultra-finely detailed pixel art UI, custom illustration, bespoke vector graphics, all underpinned by a strong design community.

Today’s web design has been in a period of stagnation. I suspect there’s a strong chance you’ve seen a site whose structure looks something like this: a hero image / banner with text overlaid, perhaps with a lovely rotating carousel of images (laying the snark on heavy there), a call to action, and three columns of sub-content directly beneath. Maybe an icon library is employed with selections that vaguely relate to their respective content.

Design, as it’s applied to the digital landscape, is in dire need of thoughtful layout, typography, and visual engagement that goes hand-in-hand with all the modern considerations we now know are paramount: usability. Accessibility. Load times and bandwidth- sensitive content delivery. A responsive presentation that meets human beings wherever they’re engaging from. We must be mindful of, and respectful toward, those concerns—but not at the expense of creativity of visual communication or via replicating cookie-cutter layouts.

Pixel Problems

Websites during this period were often designed and built on Macs whose OS and desktops looked something like this. This is Mac OS 7.5, but 8 and 9 weren’t that different.

Desktop icons fascinated me: how could any single one, at any given point, stand out to get my attention? In this example, the user’s desktop is tidy, but think of a more realistic example with icon pandemonium. Or, say an icon was part of a larger system grouping (fonts, extensions, control panels)—how did it also maintain cohesion amongst a group?

These were 32 x 32 pixel creations, utilizing a 256-color palette, designed pixel-by-pixel as mini mosaics. To me, this was the embodiment of digital visual communication under such ridiculous constraints. And often, ridiculous restrictions can yield the purification of concept and theme.

So I began to research and do my homework. I was a student of this new medium, hungry to dissect, process, discover, and make it my own.

Expanding upon the notion of exploration, I wanted to see how I could push the limits of a 32×32 pixel grid with that 256-color palette. Those ridiculous constraints forced a clarity of concept and presentation that I found incredibly appealing. The digital gauntlet had been tossed, and that challenge fueled me. And so, in my dorm room into the wee hours of the morning, I toiled away, bringing conceptual sketches into mini mosaic fruition.

These are some of my creations, utilizing the only tool available at the time to create icons called ResEdit. ResEdit was a clunky, built-in Mac OS utility not really made for exactly what we were using it for. At the core of all of this work: Research. Challenge. Problem- solving. Again, these core connection-based values are agnostic of medium.

There’s one more design portal I want to talk about, which also serves as the second reason for my story to bring this all together.

This is K10k, short for Kaliber 1000. K10k was founded in 1998 by Michael Schmidt and Toke Nygaard, and was the design news portal on the web during this period. With its pixel art-fueled presentation, ultra-focused care given to every facet and detail, and with many of the more influential designers of the time who were invited to be news authors on the site, well… it was the place to be, my friend. With respect where respect is due, GUI Galaxy’s concept was inspired by what these folks were doing.

For my part, the combination of my web design work and pixel art exploration began to get me some notoriety in the design scene. Eventually, K10k noticed and added me as one of their very

I am a creative. What I do is alchemy. It is a mystery. I do not so much do it, as let it be done through me.

I am a creative. Not all creative people like this label. Not all see themselves this way. Some creative people see science in what they do. That is their truth, and I respect it. Maybe I even envy them, a little. But my process is different—my being is different.

Apologizing and qualifying in advance is a distraction. That’s what my brain does to sabotage me. I set it aside for now. I can come back later to apologize and qualify. After I’ve said what I came to say. Which is hard enough. 

Except when it is easy and flows like a river of wine.

Sometimes it does come that way. Sometimes what I need to create comes in an instant. I have learned not to say it at that moment, because if you admit that sometimes the idea just comes and it is the best idea and you know it is the best idea, they think you don’t work hard enough.

Sometimes I work and work and work until the idea comes. Sometimes it comes instantly and I don’t tell anyone for three days. Sometimes I’m so excited by the idea that came instantly that I blurt it out, can’t help myself. Like a boy who found a prize in his Cracker Jacks. Sometimes I get away with this. Sometimes other people agree: yes, that is the best idea. Most times they don’t and I regret having  given way to enthusiasm. 

Enthusiasm is best saved for the meeting where it will make a difference. Not the casual get-together that precedes that meeting by two other meetings. Nobody knows why we have all these meetings. We keep saying we’re doing away with them, but then just finding other ways to have them. Sometimes they are even good. But other times they are a distraction from the actual work. The proportion between when meetings are useful, and when they are a pitiful distraction, varies, depending on what you do and where you do it. And who you are and how you do it. Again I digress. I am a creative. That is the theme.

Sometimes many hours of hard and patient work produce something that is barely serviceable. Sometimes I have to accept that and move on to the next project.

Don’t ask about process. I am a creative.

I am a creative. I don’t control my dreams. And I don’t control my best ideas.

I can hammer away, surround myself with facts or images, and sometimes that works. I can go for a walk, and sometimes that works. I can be making dinner and there’s a Eureka having nothing to do with sizzling oil and bubbling pots. Often I know what to do the instant I wake up. And then, almost as often, as I become conscious and part of the world again, the idea that would have saved me turns to vanishing dust in a mindless wind of oblivion. For creativity, I believe, comes from that other world. The one we enter in dreams, and perhaps, before birth and after death. But that’s for poets to wonder, and I am not a poet. I am a creative. And it’s for theologians to mass armies about in their creative world that they insist is real. But that is another digression. And a depressing one. Maybe on a much more important topic than whether I am a creative or not. But still a digression from what I came here to say.

Sometimes the process is avoidance. And agony. You know the cliché about the tortured artist? It’s true, even when the artist (and let’s put that noun in quotes) is trying to write a soft drink jingle, a callback in a tired sitcom, a budget request.

Some people who hate being called creative may be closeted creatives, but that’s between them and their gods. No offense meant. Your truth is true, too. But mine is for me. 

Creatives recognize creatives.

Creatives recognize creatives like queers recognize queers, like real rappers recognize real rappers, like cons know cons. Creatives feel massive respect for creatives. We love, honor, emulate, and practically deify the great ones. To deify any human is, of course, a tragic mistake. We have been warned. We know better. We know people are just people. They squabble, they are lonely, they regret their most important decisions, they are poor and hungry, they can be cruel, they can be just as stupid as we can, because, like us, they are clay. But. But. But they make this amazing thing. They birth something that did not exist before them, and could not exist without them. They are the mothers of ideas. And I suppose, since it’s just lying there, I have to add that they are the mothers of invention. Ba dum bum! OK, that’s done. Continue.

Creatives belittle our own small achievements, because we compare them to those of the great ones. Beautiful animation! Well, I’m no Miyazaki. Now THAT is greatness. That is greatness straight from the mind of God. This half-starved little thing that I made? It more or less fell off the back of the turnip truck. And the turnips weren’t even fresh.

Creatives knows that, at best, they are Salieri. Even the creatives who are Mozart believe that. 

I am a creative. I haven’t worked in advertising in 30 years, but in my nightmares, it’s my former creative directors who judge me. And they are right to do so. I am too lazy, too facile, and when it really counts, my mind goes blank. There is no pill for creative dysfunction.

I am a creative. Every deadline I make is an adventure that makes Indiana Jones look like a pensioner snoring in a deck chair. The longer I remain a creative, the faster I am when I do my work and the longer I brood and walk in circles and stare blankly before I do that work. 

I am still 10 times faster than people who are not creative, or people who have only been creative a short while, or people who have only been professionally creative a short while. It’s just that, before I work 10 times as fast as they do, I spend twice as long as they do putting the work off. I am that confident in my ability to do a great job when I put my mind to it. I am that addicted to the adrenaline rush of postponement. I am still that afraid of the jump.

I am not an artist.

I am a creative. Not an artist. Though I dreamed, as a lad, of someday being that. Some of us belittle our gifts and dislike ourselves because we are not Michelangelos and Warhols. That is narcissism—but at least we aren’t in politics.

I am a creative. Though I believe in reason and science, I decide by intuition and impulse. And live with what follows—the catastrophes as well as the triumphs. 

I am a creative. Every word I’ve said here will annoy other creatives, who see things differently. Ask two creatives a question, get three opinions. Our disagreement, our passion about it, and our commitment to our own truth are, at least to me, the proofs that we are creatives, no matter how we may feel about it.

I am a creative. I lament my lack of taste in the areas about which I know very little, which is to say almost all areas of human knowledge. And I trust my taste above all other things in the areas closest to my heart, or perhaps, more accurately, to my obsessions. Without my obsessions, I would probably have to spend my time looking life in the eye, and almost none of us can do that for long. Not honestly. Not really. Because much in life, if you really look at it, is unbearable.

I am a creative. I believe, as a parent believes, that when I am gone, some small good part of me will carry on in the mind of at least one other person.

Working saves me from worrying about work.

I am a creative. I live in dread of my small gift suddenly going away.

I am a creative. I am too busy making the next thing to spend too much time deeply considering that almost nothing I make will come anywhere near the greatness I comically aspire to.

I am a creative. I believe in the ultimate mystery of process. I believe in it so much, I am even fool enough to publish an essay I dictated into a tiny machine and didn’t take time to review or revise. I won’t do this often, I promise. But I did it just now, because, as afraid as I might be of your seeing through my pitiful gestures toward the beautiful, I was even more afraid of forgetting what I came to say. 

There. I think I’ve said it. 

I offer a single bit of advice to friends and family when they become new parents: When you start to think that you’ve got everything figured out, everything will change. Just as you start to get the hang of feedings, diapers, and regular naps, it’s time for solid food, potty training, and overnight sleeping. When you figure those out, it’s time for preschool and rare naps. The cycle goes on and on.

The same applies for those of us working in design and development these days. Having worked on the web for almost three decades at this point, I’ve seen the regular wax and wane of ideas, techniques, and technologies. Each time that we as developers and designers get into a regular rhythm, some new idea or technology comes along to shake things up and remake our world.

How we got here

I built my first website in the mid-’90s. Design and development on the web back then was a free-for-all, with few established norms. For any layout aside from a single column, we used table elements, often with empty cells containing a single pixel spacer GIF to add empty space. We styled text with numerous font tags, nesting the tags every time we wanted to vary the font style. And we had only three or four typefaces to choose from: Arial, Courier, or Times New Roman. When Verdana and Georgia came out in 1996, we rejoiced because our options had nearly doubled. The only safe colors to choose from were the 216 “web safe” colors known to work across platforms. The few interactive elements (like contact forms, guest books, and counters) were mostly powered by CGI scripts (predominantly written in Perl at the time). Achieving any kind of unique look involved a pile of hacks all the way down. Interaction was often limited to specific pages in a site.

The birth of web standards

At the turn of the century, a new cycle started. Crufty code littered with table layouts and font tags waned, and a push for web standards waxed. Newer technologies like CSS got more widespread adoption by browsers makers, developers, and designers. This shift toward standards didn’t happen accidentally or overnight. It took active engagement between the W3C and browser vendors and heavy evangelism from folks like the Web Standards Project to build standards. A List Apart and books like Designing with Web Standards by Jeffrey Zeldman played key roles in teaching developers and designers why standards are important, how to implement them, and how to sell them to their organizations. And approaches like progressive enhancement introduced the idea that content should be available for all browsers—with additional enhancements available for more advanced browsers. Meanwhile, sites like the CSS Zen Garden showcased just how powerful and versatile CSS can be when combined with a solid semantic HTML structure.

Server-side languages like PHP, Java, and .NET overtook Perl as the predominant back-end processors, and the cgi-bin was tossed in the trash bin. With these better server-side tools came the first era of web applications, starting with content-management systems (particularly in the blogging space with tools like Blogger, Grey Matter, Movable Type, and WordPress). In the mid-2000s, AJAX opened doors for asynchronous interaction between the front end and back end. Suddenly, pages could update their content without needing to reload. A crop of JavaScript frameworks like Prototype, YUI, and jQuery arose to help developers build more reliable client-side interaction across browsers that had wildly varying levels of standards support. Techniques like image replacement let crafty designers and developers display fonts of their choosing. And technologies like Flash made it possible to add animations, games, and even more interactivity.

These new technologies, standards, and techniques reinvigorated the industry in many ways. Web design flourished as designers and developers explored more diverse styles and layouts. But we still relied on tons of hacks. Early CSS was a huge improvement over table-based layouts when it came to basic layout and text styling, but its limitations at the time meant that designers and developers still relied heavily on images for complex shapes (such as rounded or angled corners) and tiled backgrounds for the appearance of full-length columns (among other hacks). Complicated layouts required all manner of nested floats or absolute positioning (or both). Flash and image replacement for custom fonts was a great start toward varying the typefaces from the big five, but both hacks introduced accessibility and performance problems. And JavaScript libraries made it easy for anyone to add a dash of interaction to pages, although at the cost of doubling or even quadrupling the download size of simple websites.

The web as software platform

The symbiosis between the front end and back end continued to improve, and that led to the current era of modern web applications. Between expanded server-side programming languages (which kept growing to include Ruby, Python, Go, and others) and newer front-end tools like React, Vue, and Angular, we could build fully capable software on the web. Alongside these tools came others, including collaborative version control, build automation, and shared package libraries. What was once primarily an environment for linked documents became a realm of infinite possibilities.

At the same time, mobile devices became more capable, and they gave us internet access in our pockets. Mobile apps and responsive design opened up opportunities for new interactions anywhere and any time.

This combination of capable mobile devices and powerful development tools contributed to the waxing of social media and other centralized tools for people to connect and consume. As it became easier and more common to connect with others directly on Twitter, Facebook, and even Slack, the desire for hosted personal sites waned. Social media offered connections on a global scale, with both the good and bad that that entails.

Want a much more extensive history of how we got here, with some other takes on ways that we can improve? Jeremy Keith wrote “Of Time and the Web.” Or check out the “Web Design History Timeline” at the Web Design Museum. Neal Agarwal also has a fun tour through “Internet Artifacts.”

Where we are now

In the last couple of years, it’s felt like we’ve begun to reach another major inflection point. As social-media platforms fracture and wane, there’s been a growing interest in owning our own content again. There are many different ways to make a website, from the tried-and-true classic of hosting plain HTML files to static site generators to content management systems of all flavors. The fracturing of social media also comes with a cost: we lose crucial infrastructure for discovery and connection. Webmentions, RSS, ActivityPub, and other tools of the IndieWeb can help with this, but they’re still relatively underimplemented and hard to use for the less nerdy. We can build amazing personal websites and add to them regularly, but without discovery and connection, it can sometimes feel like we may as well be shouting into the void.

Browser support for CSS, JavaScript, and other standards like web components has accelerated, especially through efforts like Interop. New technologies gain support across the board in a fraction of the time that they used to. I often learn about a new feature and check its browser support only to find that its coverage is already above 80 percent. Nowadays, the barrier to using newer techniques often isn’t browser support but simply the limits of how quickly designers and developers can learn what’s available and how to adopt it.

Today, with a few commands and a couple of lines of code, we can prototype almost any idea. All the tools that we now have available make it easier than ever to start something new. But the upfront cost that these frameworks may save in initial delivery eventually comes due as upgrading and maintaining them becomes a part of our technical debt.

If we rely on third-party frameworks, adopting new standards can sometimes take longer since we may have to wait for those frameworks to adopt those standards. These frameworks—which used to let us adopt new techniques sooner—have now become hindrances instead. These same frameworks often come with performance costs too, forcing users to wait for scripts to load before they can read or interact with pages. And when scripts fail (whether through poor code, network issues, or other environmental factors), there’s often no alternative, leaving users with blank or broken pages.

Where do we go from here?

Today’s hacks help to shape tomorrow’s standards. And there’s nothing inherently wrong with embracing hacks—for now—to move the present forward. Problems only arise when we’re unwilling to admit that they’re hacks or we hesitate to replace them. So what can we do to create the future we want for the web?

Build for the long haul. Optimize for performance, for accessibility, and for the user. Weigh the costs of those developer-friendly tools. They may make your job a little easier today, but how do they affect everything else? What’s the cost to users? To future developers? To standards adoption? Sometimes the convenience may be worth it. Sometimes it’s just a hack that you’ve grown accustomed to. And sometimes it’s holding you back from even better options.

Start from standards. Standards continue to evolve over time, but browsers have done a remarkably good job of continuing to support older standards. The same isn’t always true of third-party frameworks. Sites built with even the hackiest of HTML from the ’90s still work just fine today. The same can’t always be said of sites built with frameworks even after just a couple years.

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