As a 5-year employee of Automattic, I have the option of taking a 2-3 month sabbatical. I opted for the shorter duration as I felt it was a good amount of time to get some artwork created and some studying done on being a stronger leader in my design community, so that I could come back to work strong. I felt like a 3-month break would have been too much time to get lazy and bored, making for a bad re-entry to work.
Before my break would start though, I’d have an inspiring last bit of work to do in Denmark with the Automattic Design Team (the half that wanted to travel to Copenhagen, that is. The other half went to Atlanta).
During a jetlag-fueled haze, I quickly wrapped up the badges and schedule designs for WordCamp Denver. My first official week off included spending some good time with my kids, the longest time I’ve had with them since their mom and I separated in mid-2014. I also spent time that week designing the slides for my WordCamp Denver talk “Full-Stack Web Design: A Case Study in Interactive Prototyping”
Something Along the Lines of Dating
Between Copenhagen and WordCamp Denver, my girlfriend Beth and I got to see the premiere of a movie that we’d been extras in over a year ago called Something Along the Lines of Dating:
Since I’ve now got an amazing apartment, I finally took the time to decorate it how I like:
One of the main reasons for this sabbatical was art. I spent some time getting back in touch with my art school education by doing some drawing and painting: skills I don’t use in my every-day professional work, done with tools I’ve allowed myself to become unfamiliar with. Time to change all that.
I’d long had a blog series in draft form saved away that I wanted to flesh out and spend more time getting right before I published. This series turned into the Why I’m a Designer series on this blog that I started posting early into my break. I have 4 more parts planned, but I have some studying to do first.
Part 2 of this series is titled View Source and it’s a concept I’ve decided to flesh out even further by writing an Almost Famous-type film loosely-based on a fictionalized account of my first real job in the early days of the web. I was inspired by attending the premiere of the film I’d briefly appeared in; it seemed possible for me to actually make something worth watching. The rough writing I’ve gotten done is a baby step in that direction. I’ve been watching films by my favorite directors trying to study their work.
Since writing isn’t a strong suit of mine, I decided to mostly tackle the View Source film through its music. I first created a Spotify playlist of the music we used to listen to in the office at the time, music that lived inside of a 300-disc CD changer that also powered what people calling the office heard when they were on hold. I augmented this list with music I was personally listening to a lot at my first job.
Original Motion Picture Soundtrack
The second part of this approach was to record an original motion picture soundtrack influenced by music made in the 1998 – 2001 range.
I also wrote these songs I’m not sure what else to do with:
I was very glad to spend some extended time with my kiddos this summer.
The Gin Doctors
I got to see my friends and Denver’s Best Cover/Tribute act (according to voters in The Westword) The Gin Doctors a couple of times this summer, which is always an incredible time:
I found reasons to use these images:
Underground Music Showcase
I got to go to a couple nights of The Denver Post’s UMS event held on South Broadway. Highlight of the event for me was an epic performance by Denver’s own Slim Cessna’s Auto Club:
I got to go a wedding in Vail:
In general, there’s nowhere else in the world I’d rather spend two months re-energizing and getting back to my creative roots than Denver.
Then something funny happened that we weren’t expecting, but sort of hoping for: the web became a tool everyone used, all the time, for a ton of reasons.
New users were arriving online every day, and new services were popping up in droves to give them fun stuff to do there. Years after Wall Street left the “dot-coms” to die in the gutter, the former employees of these companies built new tools, with new ideas about what a web interface could accomplish.
Web users adapted and started to actually love the products they used online. Flickr, Twitter, Tumblr, Del.icio.us: we all have memories of what was new about these things when they first appeared that delighted us.
The web was a super-fun place to be, both as a user and designer.
2001 – 2010
I spent the intervening years doing the following:
Learning and forgetting Flash, ActionScript and Flex
Building in CakePHP and taking offline a web app for people to record very personal data
Spending 6 months designing a 15×10 GIF (among many other things) for the front page of the New York Times
Getting a job where I designed screens for people with mental disabilities as well as for people whose job was to support those with mental disabilities
Watching the idea of “mobile” evolve from WAP-based apps rendered on Handspring devices to the responsive web and iOS/Android apps we have today
Getting a job at Automattic, working on the blogging system I’m using to publish this very post.
I can honestly say that during those 9-10 years, my work was used by millions of people, and that by 2010 my work reached that many people daily. I learned a lot during this time about how people use web applications, how they share content on the web, and how they talk to one another with the tools we build. I learned what my medium was being used for (fun fact: in 2002 I owned the domain “automaticmedium.com”) above and beyond what I was personally using it for. And all this time, I blogged.
I used a system built in PHP3 my friend Tai and I paid $500 for and then I ported that blog to a custom system I wrote in PHP 4 which I then wrote a custom importer for in 2007 that pulled it all into WordPress. Blogging was and is important to how I work.
Ego & Empathy
While designing and building the tools my clients asked me for, I was simultaneously either plugging away at a new CSS idea on my blog, or trying out a new language to build a web app. My craft and I grew up at the same time and I tried to stay involved in it above and beyond my client work for two simple reasons:
Ego: I needed a place to play. Client work was now very serious and very important and playing with new ideas often wasn’t the best choice for these projects. Not to say we didn’t pitch new ideas, they just often weren’t chosen for development. Knowing I should and could keep my code chops up by playing on my blog was important to me for increasing the quality of my work.
Empathy: I really wanted to have my own site with an audience and user base that I considered my own. This way, I could truly understand a client’s desire to do right by their users because I spent evenings and weekends making something for my own group of people I wanted to please.
These two concepts seem diametrically opposed: Ego and Empathy. I contend that to design a web application that people want to use on a daily basis you need both the ego to say:
“I can make something people will want to use that’s better than what exists”
and the empathy to listen to what your users actually say when you launch it. Additionally, your empathy for what you’d want on the screen you’re designing goes a long way toward making something your users may want to use.
Try All of the Things
How do you build this empathy? One of the ways besides maintaining a web app by yourself is to be a die-hard trier-and-user of any and all web apps. Really use them for really real things. See what making boards on Pinterest is all about. Follow art blogs on Tumblr and check it every day. Try Snapchat and get confused and close the app forever. Stuff like that.
You can start to understand what else the rest of the world is doing with their digital devices on a daily basis; you can see where your app fits into your users’ lives, not just how your users’ lives fit into your engagement cycle.
Empathize with what your users do on a daily basis with your tool by doing the same things with it and by doing the other things they do on a daily basis on the web, too. Pay fucking attention to what works and what doesn’t and why. You can start to synthesize this information with the designer’s ego telling you that you actually can produce a better product. What can result is remarkable: an app that people love using.
That’s always been my goal for my work on the web: to make something that people love having in their lives, something that feels like humans made it for other humans. They’ll come back over and over and give you their money for things you’re building that they want to use. You won’t have to beg for money from people who want to pay you for what you make.
Last time, I mentioned that we had 2-3 designers simultaneously pitching ideas to clients. What I omitted then but would like to clarify now is that each designer determined for themselves absolutely everything they pitched:
Navigation structure and labels
Content blocks and layout
Interactive tools & functionality
Branding & logo work
Visual design system execution
What this meant was that often a client would see different versions of all of the above in the same meeting. They couldn’t focus purely on the competing designs’ visual directions because they’d also be picking a navigation structure and maybe even a logo at the same time.
This was a pretty terrible process. Factor in that Project Managers also didn’t exist and unsurprisingly lots of confusion resulted all around. Designers would pitch competing and usually slightly misinterpreted ideas the client floated in earlier discussions. We’d catch a glimpse of the other designer’s work and decide to incorporate some of their concepts, creating a miasma of ideas presented all at once, similarly sourced but slightly tweaked.
These were incredibly rare devices and when our new office manager Jen Mylo (née Wells) needed to find it, there was something about her wording that immediately made me envision our plastic brick of a cell phone sitting on a bar stool, smoking a cigarette, talking shit about the employees that lugged it around the city. It cracked me up.
I immediately replied-all and said “I saw it a bar last night; it doesn’t want to see you.” My intention was to be funny and set a new employee at ease, that we had fun at this company. What actually happened was that she thought I hated her, which I learned a few days later when we were both part of a small group tasked with picking out a new office pinball machine.
I think I was the only one with a car at the time so I offered to drive. It was on this formative drive to Lakewood when I learned:
Just how professional, detail-oriented and experienced Jen was and
Just how bad I’d made her feel by being unprofessional over email.
I’m incredibly lucky that we cleared up the misunderstanding that day, chose a sweet new pinball machine for the office, and made friends for life (so far).
Roping the Dude Ranch Operator Back to the Web
When she spoke to Spiremedia co-workers about her life and work experiences, she was quick to mention her time on a dude ranch in Arizona, as an activist for Greenpeace, as the supervisor of a food co-op and many, many others. What she’d purposely be quiet about, and left off her resume entirely, was her time working on the web as an Information Architect. She was at the moment living and working in Denver along with her boyfriend, and wasn’t sure if she was staying long, so doing serious web work here wasn’t really on her list of priorities. “I really don’t want them to know I know how to do this” she’d quietly mention.
Of course “they” did find out about this unexpected IA on staff and quickly put her to work on our clients. By this time we had a team of 8-10 designers pitching sometimes totally off-the-wall ideas to clients and generally running the asylum. There was one incident where I went on vacation and left another designer in charge of my client work, only to return to a totally functionally-altered concept. Jen changed all that.
With the addition of Jen to our design team (as well as three experienced project managers: a lot changed for us at once), the process started to resemble something sane:
These newly-added PMs would work closely with Jen and the client to determine what the site actually needed at a functional and content level
Jen would propose and refine a site architecture and content deck. She would then wireframe this architecture and content layout, staying as design agnostic as possible. I still wish I understood how to do card-sorting as well as she did then.
These documents would stand as blueprints for the designers to start molding into a visual model. Any specific design decisions in the wireframes were up for interpretation (size and placement of content, visual relationships, etc) and a serious effort went into the visual impact of the site.
Once this work was complete, our developers now had both abstract definitions and concrete examples from which to synthesize the working site.
Clients no longer had competing, complete design philosophies to pick from all at once: each visual design was now proposed with the same labels, the same content, and the same architecture as the others in the meeting, and it had all been already determined. By working with Jen first, client expectations were set for what to get from the visual design staff and our expectations were set for what the client actually needed.
She enabled success on both ends of the spectrum by advocating for the users to the client early in the process, and then she’d pivot and advocate for the client and users to the designers when we came in later.
I now had two mentors helping me establish two keystones of my design philosophy:
Scott Upton solidified the value of designing for the web by using the fabric of the web itself: HTML and the browser. He taught me that using your interface as your design it is the only way to know it works.
Jen Mylo locked in the absolute necessity of hearing what your client and their users are saying, filtering it through the way your experience has shown you that people actually use the web, and turning that around as smart recommendations and decisions upon which to base your visual design.
I’ve plotted just about my entire career path between these two ideological pillars of how to build for the web. I’ll explain in Part 4 what I’ve done in the last 15 years with this foundation.
As I stood in the cramped first-floor hall of the 300 building at the Art Institute of Colorado, my heavy bag of supplies dug painfully into my shoulder. I was with a friend and we were looking for jobs on the board, a task I undertook when I found myself in each of the three buildings we had on campus in Capitol Hill for the first time that week. As soon as we walked up, one posting in particular jumped out at me and I forgot all about the huge bag on my shoulder. It said in stark Franklin Gothic Condensed type:
SPIREMEDIA IS HIRING A RECEPTIONIST
which I’m sure doesn’t sound to you like that big of a deal, but to me it was like that paper was etched in gold. I’d been doing web design hourly for a small shop owned by a man who – in a daze of inspired light and beauty – named his company The Internet Design Firm. During my first week at this job I AltaVista’d (we didn’t Google back then) “Denver web design companies” to see what was happening in town, and to find work that could inspire me in times of need.
Spiremedia was an agency I found during this search whose portfolio suddenly redefined for me what a web site could look like, what the web could be. I had already spent a lot of time on their site, poring over the portfolio looking at the decisions the designers made on each piece, trying to determine what I could learn from them.
“What about this work is applicable to my own? What can I discard? What can I change about what I take, to make it my own, my clients’ own? How did they code that?”
It wasn’t just their client work, either: their own site was an excellent example of the thinking that went into everything they designed. I never dreamed I’d actually end up working there. I was a student who had done a total of 10 months of contract work in the industry, not one of the professionals these people clearly were hiring. I’d click “view source” in my browser, copy out some of their clever HTML code, and learn from their ideas.
And so but here was this flyer stapled to the wall, telling me they were hiring a receptionist. The privilege of my education leapfrogged me past wanting to apply for the job for which they were actually hiring, so my email’s subject line said “I don’t want to be your receptionist” and the body included a link to my portfolio telling them I’d admired their work for a while, and that I wasn’t a very good receptionist but I was wondering if they were hiring designers. I couldn’t have been happier when the reply came that they wanted an interview, but I had no idea what to expect.
What I found when I showed up was incredibly disorienting: the building was out past Lower Downtown (the newly-named LoDo), on a street no one I knew had heard of. When I pulled my car into the dirt expanse in front of the building, I suddenly recognized it: this was the terrifying part of town where we parked our cars back in high school to go to St. Mark’s Coffee House. The concrete and abandoned 5-floor building at the edge of the dirt lot wasn’t so intimidating during the day, it seemed. What on earth was I going to find inside the warehouse across the street?
I couldn’t have guessed that it was going to be about 5,000 square feet of exactly what I’d been looking for since junior high, but this was not an office that my work experience had prepared me for. There was no sterile drywall bound by drop-ceilings and cheap carpet. There were no medical-grade waiting room chairs or neckties. No one was freaking out about the dogs wandering around and no one appeared to be over 30. Everyone wanted to be there.
A video created by Scott Upton with an original iBook and external video camera
Thick, wooden warehouse columns broke up the space into distinct areas. Existing long before many floors of offices had been built around them, they stood like stoic Redwoods throughout the office, ancient and real. I marveled at how many people must have done how many kinds of work in this building near these columns, and noticed this group of people covered them and the exposed brick in artwork and ethernet cables. The waiting area for clients was made up of a duo of (also wooden) old-timey school chairs which faced pinball and Asteroids machines. The music was loud and the person interviewing me had about 1,000 toys on his desk in the only private office I could see.
I was home again.
The Year 2000
Spiremedia often worked in a traditional design agency model: 2-3 designers were assigned to each new project and tasked with designing something totally different from their counterparts. The client would choose a design (or they’d make the worst of all possible decisions and combine two of them), and the designers whose work wasn’t picked would go on to new projects. The selected designer would work with the client to design each page, using whatever tools necessary, and hand it over to development to build. This was and continues to be a super common way to do web design, but the end result is that you’d usually get your designs built not quite right by the developer.
Part of doing web design was (and continues to be) understanding what the medium is capable of. If we designed something crazy or just not-quite-possible, we’d get an approximation of our designs live on the web and this was a thing I’d get sort of sad about. I wanted my pages to look and work how I designed them, dammit.
What Sucked About The Web
I alluded in Part 1 to a tendency of entirely visually-focused graphic designers to make fun of the web in 1999. At the risk of sounding incredibly “get off my lawn” about it, here’s an incomplete list of things we didn’t have as web designers when I started out:
Fonts. We could set our page’s text in any font we wanted as long as it was Verdana, Arial, Trebuchet, Georgia or Times as these fonts were available on most platforms. Using one of them ensured your pages looked similar to the highest amount of potential users. Want a different font? Time to make a bunch of header graphics!
Fast Internet. Most of us still had 56k modems at home but at work we used expensive lines that still were geologically slow by current standards to build and launch sites that hoped to gain mass adoption. We were building tools that aimed to be useful in a technical universe that hadn’t quite arrived yet.
Colors. “Colors are darker on Windows” was a common refrain heard around the office. Clients never saw the colors we saw on our Macs because have you ever tried to color-calibrate your client’s Windows NT-running-computer’s monitor? Of course you haven’t because it’s impossible. We always assumed the colors we chose were mere suggestions for how the end-user’s computer would render them.
YouTube. Seriously, think for a second about the web before YouTube or much video of any kind. See also: Google, Facebook, Twitter, Blogs, Spotify, StackExchange. We did have the real Napster, though.
What Was Awesome About the Web
Without a clear mode of operation to follow, we got to make things up. We tried to figure out what this new “web interface” idea should really look and feel like, given the limitations of the browser. We couldn’t do the UI heavy lifting you had on the desktop, and the whole idea of pages broke the application metaphor anyway.
We improvised and we changed course quickly because that was and continues to be the benefit of designing for our platform:
We weren’t desktop software designers because they had low-level control over their UI and could respond instantly to user input. Flash was the closest we could get but it felt like cheating to use it.
We weren’t graphic designers because we had web text to deal with, and navigation, and clicking, and scrolling. People had to use what we designed, not just look at it.
We weren’t multimedia designers because we used a document markup language to code our screens and we had to factor in a page load between each click.
We weren’t developers because they used ColdFusion and SQL and PHP and other acronyms I didn’t understand.
Linking Leagues and Asking Why
My first two clients were businesses commonly referred to as dot-coms to denote their internet-only status. My official title was Production Artist and my job was loosely defined as helping designers put their work on the web. My first two projects ended up being simply design projects that I used code to produce, which has impacted my entire career to-date.
The first work I produced for Spiremedia: a Flash intro for a site that hadn’t launched yet
The actually-launched site
Why.com (forever embedded in my brain by its clever logo leveraging a question mark for the dot: Why?com) was assigned to me at the same time. This was a search engine that included a social aspect: other users were able to rank, rate, and recommend search results for given terms. Apple launched a service called iReview not long after, effectively killing the company. Two things stand out during my time working on why.com: it was the first time anyone in our office had heard of Google, which powered our search results (we thought it was a weird choice), and it was this project that provided me with my first business trip.
I didn’t realize it at the time but Scott Upton, my lead on the aforementioned projects, was also the designer whose work I’d most admired in the company’s portfolio from afar. I still haven’t had a creative director quite like him for three reasons:
He was doing the work himself, and his structural decisions cascaded down to the specific screens I was working on. Any style I’d developed in school or on my own was out the window, it was time to explore someone else’s partially-defined design system and extend it.
There were no Photoshop files, as he was building a clickable prototype, a shadow-version of the functional web app being built by the client. The code wasn’t for production but it made the creation of new screens so much faster and more compelling than doing flat Photoshop work. We could use our site as we designed it, and could tell when an idea wasn’t working long before users or the client saw it.
He was patient and always advocated for the user’s best experience. I envied his ability to sketch in front of a client to get buy-in on a better idea than what they were floating back to us. Cleanly-drawn lines and clear ideas won out – most of the time.
For the first 6 months of my professional career, code and design were one and the same. There wasn’t a developer alive who’d touch Flash at that time and having our hands in the code of a site, no matter the language, gave us a control over the end-result that no amount of wire-framing or Photoshop mockups could give us. The client would usually see screenshots of our work, but that work’s production had a web-native methodology baked into it; we knew the screens we designed could be executed in code because we were already doing it.