What I Did On My Summer Vacation

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:

Apartment Decorating

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.

Some of the elements in this design are over 15 years old
Some of the elements in this design are over 15 years old

I also wrote these songs I’m not sure what else to do with:

Kid Time

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:

Vail Weekend

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.

Why I’m a Designer Part 3: Finding Order in the Chaos

This post is part 3 of a series. You can read Part 1, Part 1.5 and Part 2 if you’d like.

Y2K (Contd).

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.

Then Jen showed up.

Office Cell Phones and Pinball Machines

The subject of the all-employee email read

“Has anyone seen the office cell phone?”

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:

  1. Just how professional, detail-oriented and experienced Jen was and
  2. 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:

  1. 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
  2. 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.
  3. 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.
  4. 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.

Why I’m a Designer Part 1: A Timeline

This post is part 1 of a series. You can read Part 1.5Part 2 and Part 3 if you’d like.

1979 – 1991

Me at Sea World before we knew it was evil
Me at Sea World before we knew it was evil

I was an “Arty Kid.” I have no idea whether this is because my genes conspired to make art a thing I could do or if I simply had enough people tell me I had artisitc ability so I internalized it as best I could, but either way my childhood included an awful lot of drawing. The neighborhood recreation center was where my brother played basketball games, but I remember it as where I attended my first art class at 7 years old.

Art taught me how to create a space in my brain to play with a visual idea, and how to make that idea happen on paper. It also taught me how to learn from a failed experiment and try again on a new piece of paper. I often used my worksheets for this instead doing of the boring work that I already understood on the front, to many of my early schoolteachers’ chagrin.

I was also a “Computery Kid” but I don’t remember anyone telling me I was a Computery Kid because computers weren’t readily available until I was about 7. Once I started using them, I never wanted to stop and I was comfortable enough with computers that by the 3rd grade, when our classroom received an Apple ][ that none of the adults knew how to hook up, I could look at the wires and see where each one fit. By just trying them out I got it working, and I think that was probably the first time I was called computery.

When the Macintosh came out, my first exposure to graphic design was alongide my cousins as we used MacPaint to print out 10-page-long banners connected with that special dot-matrixy paper. As we spent hours designing Happy Birthday banners, I’m sure we used tons of my uncle’s paper but he never seemed to mind. I loved computers when I was a kid: they were clearly tools for making art.

1991 – 1994

For junior high (grades 7–9), I attended a computer-math-science magnet school that bussed kids in from all over San Diego. Each year, along with our intensive math and science classes, we also attended programming classes. I took my first coding class at a public school when I was 12 years old in the early 90s, something I could never have appreciated the rarity of back then, but now I know that access to educational programs like this is an opportunity not afforded to many young kids.

Bell Hr. High
Bell Junior High School, San Diego, California, 1993. Taking Instagrams before it was cool.

We didn’t have enough machines in the labs for each student, so we were paired up and wrote our code as a team for each project. The first team project in 7th grade was to create a frame-by-frame animation in BASIC by coding each individual frame’s pixel’s placement on an 80×80 grid, wiping the grid, and drawing the next frame. My partner Quentin and I coded a windmill that had two frames so that when it looped, it looked like the windmill’s blades were spinning. I like to think we were making 8-bit animated GIFs before browsers were invented.

While it’s true that this was my first exposure to coding, it was conveniently also a visual task: I was making art with computers. For all I knew, all of programming was about putting cool stuff on a screen for people to see.

Help screen for creating a button with HyperCard

In the 8th grade, we learned about scanners and my partner Kenny and I used HyperCard to make an interactive Myst-like game, introducing me to my first onMouseUp event, a concept I had no idea I’d implement over and over again during my adult years.

Freshman year was where things got harder: our code was now to take a user’s input, use functions to perform math on that data and return the result to the screen. As we coded Pascal-powered forms to tell us how many cords of firewood we’d get from a theoretical tree, I again focused on the way data looked as it was displayed on the screen. My partner Lauren had a much stronger grasp on the math and data-processing side of the language and without her as a partner I doubt any of my projects would have gotten completed.

What I learned that semester, at Lauren’s expense, was that when the code had to start doing things that strayed too far away from a visual result, there were other people in the world who took to those kinds of hard jobs better than myself. My skills came into play when something needed to happen on the screen. As I later learned ActionScript and JavaScript, I had clear recollections of Lauren’s patient tutoring on how to use closing curly brackets.

What I was beginning to experience in school was an environment I’d essentially continue to search for my entire career: a smart, diverse group of collboratively-focused and really smart people working together to make digital art.

1994 – 1997

As my time at Alexander Graham Bell Junior High came to a close, the gap between my art and use of computers started to widen. Now attending a much more tradtional high school in Colorado, my access to technology in creative capacity was very limited for my sophomore and junior years. The ironically much better-equipped computer labs at my new school appeared to be used entirely for things like Excel spreadsheets and Word documents: the kinds of things that made me want to bang my head against the keyboard and start drawing on the margins of the page again.

My move to a suburban school in Colorado also came with a huge cultural shift for me. Saying I didn’t fit into my new school is an understatement as there were particular groups who actively and at some points violently rejected weird people like me. I turned to artistic pursuits to make it through this time and reconnected with the self-expression and healing that art could provide.

Making drawings, writing angsty poetry and playing my guitar filled my afternoons and weekends. This technical and cultural dark age was crucial to me finding the self-validation that art could provide and it gave me the time to get better at it. As long as I was expressing my emotions with art that improved in quality over time, I could deal with anything the lacrosse players wanted to call me in the hallway.

As senior year came into view, things started looking up. I had found a large group of outcast and cynical people at school like me and it was with this re-found confidence that I joined the school newspaper staff as an elective and found myself once again staring at a computer that expected me to make something with it. My first year on newspaper staff as graphic artist and music columnist also marks the first time a high school newspaper was 100% digitally-produced in Colorado. Every other high school here was still mocking up their pages with printouts and glue and tape, sending camera-ready art to the printer instead of digital files.

Macintosh Performa 5200 LC
Macintosh Performa 5200 LC, only available to education markets. My music column was called Cognitive Dissonance, I shit you not.

While the writers on staff used the 9-inch black and white Macintosh Classics along the edge of the room, I was allowed to use a much larger PowerMac 5200 LC that had a scanner attached to it and Photoshop 3.0 installed.

I felt home again.

I made graphics for the newspaper during school hours, but after class I’d hang out, scan my drawings and edit them in Photoshop. I’d go on the weekends and take photos downtown, then I’d scan the prints so that I could blend them into weird images to print and hang in my locker. I still wasn’t sure what the words “graphic design” meant but when my newspaper teacher suggested I do an independent study on it for the second semester, I jumped at the chance. Overseen by both the newspaper teacher and the director of the art department, I was allowed to investigate what graphic design was, produce pieces that no one had assigned to me, and get ready for college: a graphic design program at art school.

I simply cannot overstate the importance of a few key teachers in my life as well as the technology available at school and in my extended family’s homes during my childhood. I can’t imagine who or where I’d be without them.

1997 – 1999

I worked through college doing digital pre-press 3 blocks away from campus, spending my working hours pre-flighting and printing many of my fellow students’ work. I’d punch out and stay after countless evening shifts to continue printing and mounting my own work, supplies for which were available to me at a steep discount from my employer. I was spending 10-12 hours a day thinking about and producing design work.

I spent so many hours staring at this thing, hoping it would do what it was supposed to
I spent so many hours staring at this thing, hoping it would do what it was supposed to do

But something about the print world didn’t feel quite right. The amount of work that went into taking a QuarkXpress file from someone’s Zip disk and getting it to print correctly from our digital printers was obscene. There were crucial details that could be easily overlooked by the customer, rendering their prints completely useless. As school got closer and closer to completion, classes started leaning heavily on the student’s ability to go and get offset prints produced: an expensive task that I had zero interest in learning how to do.

The web was an obvious alternative as I could start going behind the scenes on the computer-side again. Instead of using someone else’s interface to create art, I was back to writing the code for a UI itself, a task I’d been introduced to with HyperCard stacks 6 years earlier.

The web was also a weird choice for a designer to make at that time. I’d be giving up fine typography control, throwing any semblance of faithful color reproduction out the window, and embracing lower resolution over higher. And I did this willfully and aggressively because I could make something, and I could make it fast, and people could see it anywhere in the world in seconds. Why on earth would I care about printing things?

As my formal design education was nearing its end, I landed my first salaried web design job in 1999 without a resume at a company that wasn’t hiring a designer. I simply emailed them a link to a portfolio I designed and built in Flash. Within a week I had an interview and I started work less than a week after that. I could now call myself a professional designer.

Up Next: Why I’m a Designer Part 2: View Source

Stoner tales, the first in a series

I am not a pothead.

What’s funny is that it’s 4:19 pm as I’m sitting down to write this.

The disparities between the 4:20 urban legend’s reality and its myth are indicative of the problems inherent in the larger marijuana/cannabis culture on the whole: simple, utilitarian truths get surrounded by misinformation and foggy-headed speculation. It’s been explained to me that 420 is the number of molecules (uhh) in THC or also that 420 is the San Francisco Police Department’s code for a marijuana violation. 4:20 appears as the optimal and not-so-secret time for smoking, but these explanations are silly and don’t explain how this time became the numerical placeholder for cannabis culture.

The truth is that it was simply a time some students at San Rafael High School chose to smoke up as it was convenient for them, and the number flowed organically within that community as an artifact of its particular culture. It also turns out that 4:20 is a pretty damn good time to imbibe, so the term has stuck and so has the ritual of the time. There’s no secret handshake or Grateful Dead shirt required, and common sense gets extended to future generations in perpetuity. This happens with stoners more than you’d expect, actually, and what’s funny about it being 4:19 pm when I sat down to write is that I didn’t even realize what time it was and simply glanced at the clock to see how close to 4:20 my smoke session just was. It turns out I smoke or vaporize at around 4:20 pm even when I’m not trying to.

But I am a stoner.

Now, you probably know me, and depending on how well we know each other, you may or may not know that at the ripe age of 31, and for a number of reasons, I essentially decided to forego alcohol entirely and wholeheartedly embrace the plant known scientifically as cannabis sativa and cannabis indica for quite a few of my everyday needs and wants instead. A quick rundown on the differences in my mind between a pothead and a stoner:


  • No job
  • Probably some kind of hippy
  • Smells
  • Smokes to get stupid high (somewhere in the 8-10 range on the scale of highness, with a 10 being so high that you’re uncomfortable and want it to end)
  • Doesn’t give a shit about strain or phenotype
  • Plays video games
  • Is annoying when high


  • Functional and productive member of society
  • Drives a new car with regular payments
  • Smells like rich mahogany
  • Much more likely to use a vaporizer for stealth and health
  • Smokes for actually, really, for really-real medical purposes during the day and at bed time
  • But knows when to get recreational with it and tailor usage to parties in ways many others use alcohol
  • Has medical card
  • Plays video games, too, but not as many?
  • Is awesome when high

Legalize it!

One thing that potheads and stoners typically have in common (besides a love of the herb) is a heartfelt devotion to legalization, and a somewhat paranoid attitude toward revealing your smokerness to those who may not approve for legal reasons.

Except that where I live (Colorado) we did legalize it. And even before that I was legal because of my medical card. Fuck paranoia and fuck those people (whoever they may be, I’m not entirely sure they exist in any real numbers), I smoke weed, and here’s why.

Let’s start with alcohol, because that’s really what spurred this whole thing on, in an indirect way. I’ve never particularly loved drinking. I didn’t get blotto on my 21st birthday; I was sober enough to drive home. But as a weird kid in high school, beer was not for me on principle and I never grew into it, and the drink I did enjoy was completely reviled by my friends. I ordered it as “Gray Goose and cranberry” but we all know I was asking for a Cape Cod (or Sea Breeze, whatever). So even when I did drink, I wanted it to taste like candy and not alcohol. Then within a couple of years, my wife and I had two formerly close friends from high school get essentially brutally and violently torn from their lives because of alcohol.

The first was Arlene, a woman who’d been a bridesmaid during our wedding. She died early on the morning of what was to be her own wedding day, after getting her dress altered one last time. She was hit and killed on Hampden Ave by a drunk driver who’d had previous DUIs. Her dress was hanging from the window of the shattered car. This ended any kind of semi-drunk driving I’d been doing until this time.

About five years later another formerly close friend from high school named Joe Goolsby died. Joe’d always had a problem with bipolar disorder and doing things to excess and even when we started drinking in high school and early college, as I was finding hangovers less and less intriguing, he was becoming more and more dependent on alcohol for daily existence. In 2010, as I was in the very early stages of making in-person contact with him again after hearing stories from our other friends about how his alcoholism had brought on alcoholic neuropathy and how miserable this made him to be around as he was in constant pain, I received news of his death.

I’d been told that he couldn’t drink anymore because it’d kill him if he had but he felt that he couldn’t not drink because of the constant pain and inability to function or even eat while sober. He died suddenly of causes that have never been explained to me. I hate to think he did it on purpose, but I can’t know that. The even more fucked up thing is that Joe died within two weeks of two other people from an extended former group of friends from school, both of whom died from the very same problem.

So you hate alcohol, and?

And so I got really and truly depressed from all this. The night before his funeral, I could tell that I wasn’t going to sleep, I needed an outlet,  something to cover up that pain that I was feeling and it seemed like drinking myself into a stupor just really wasn’t the most respectful choice. I called up a friend and asked him for some of his weed, and he kindly gave me all that he had which while not much was enough to dull the pain, to help me dissociate – even if it didn’t help me sleep (I’d find out why later).

On top of a general bad mojo I’d felt while drinking after I’d been on some anti-anxiety medication at the time, these losses of life in exchange for liquid poison just didn’t make sense to me, it didn’t seem like a fair trade, and here was an alternative that by all signs seemed to be a harmless plant that could do some real good for me. So I went green.

Next up: growers, smokers and sellers, oh my!