The Shoes Were Wrong

I have never taken a design class.

Twenty five years in, that's still the first thing people are surprised to hear, and the least interesting thing I could tell you. The absence was never the story. What I did instead is.

It started with a magazine.

It was 1995. I'm on the floor with a copy of SLAM magazine, and there is an ad for the Nike Air Go LWP.

Back then I didn't really know anything about shoes but I knew that one immediately and completely, the way you know things at eight years old. Nubuck upper. Speed lacing. Light Weight Performance, a phrase I could recite well before I could have spelled either of the first two words.

I did not have that shoe. I had a photograph of that shoe. And I looked at that photograph until the page went soft.

That's where all of this starts. Not a career. But instead with a picture of something I wanted.

I never got the shoes. But I did get shoes. Then more shoes. Then what any reasonable person would call a collection, and what made my mom wonder how I got so many shoes. But that’s a story for another time.

The splinter

By middle school I was playing NBA Inside Drive 2000 on my computer, and the shoes in it were wrong.

So were some of the uniforms. A team was in last season's jersey. Somebody else was wearing a model he would never in his life have laced up. Or in a pair of the default generic shoes. It sat in my chest like a splinter.

A normal kid notices this and keeps playing.

I went and found a pirated copy of Photoshop. I opened the file system in the game and found the individual shoe .bmp files the game referenced and started correcting shoes and uniforms. 1 pixel off and the game would crash. You had to be precise.

I didn't know what I was doing. I didn't know there was a word for what I was doing. Nobody in my house was a designer, there was no class at my school, and I had no ambition of any kind. I just knew the shoes were wrong, and that there was apparently a program that could make them right.

The photograph taught me to want things. The video game taught me I could go change them. Everything after that is the same move with higher stakes.

The move

Here's one of my secrets, since I've now done it for twenty five years.

See a thing. Want it different. Take it apart until it does what you want.

That isn't a work ethic and it isn't passion. It's closer to an itch.

Nobody has ever assigned it to me.

There are two ways into this. One is to learn the principles properly and then go find problems worth applying them to. That's what school is for, and school is good at it.

I went the other direction. I always had the problem first, and I'd go get exactly as much knowledge as that one problem demanded and not one inch more. Efficient. Also full of holes.

High school was Dreamweaver. I wanted a website, websites required code, so I learned enough code to get the website. Then MySpace and Xanga, which for a certain age of person was the greatest design school ever accidentally constructed. A profile page you could pour HTML and CSS straight into. A whole generation of teenagers learning CSS overrides because they wanted their page to look sick.

I didn't know I was training. It felt like messing around. It was messing around. It was also the beginning of my ten thousand hours.

Ecology

In college, I majored in Ecology.

I'd love to tell you there was a plan. There was not. I liked it, it was outside, I liked animals, and at nineteen I found "what are you going to do with that" to be a rude question.

But ecology is the study of systems. Nothing in an ecosystem means anything by itself. You can't understand the fish without the water temperature and the algae and the thing that eats the fish. You learn to look at a mess and find the dependencies. You learn succession, which is how a burned hillside comes back, in what order, on what timeline.

Fifteen years later I would spend years building design systems, which is a document about dependencies written for people who might show up when you're not there.

The only formal education I ever got turned out to be the right one. I just took it in a building with no computers in it.

The luckiest bad timing of my life

My work study job in college was graphic designer for the school, which is the first time anybody paid me for this. I designed posters for events on campus, those little placards next to exhibits in the university's art museum, and even a little web work every now and then. Then sprinkle in summer internships at ad agencies and OMSI. Then I graduated into the middle of the Great Recession.

Which is the single luckiest thing that has ever happened to me. It took about six years to notice.

At the time it mostly meant there were no jobs. So my best friend from high school, his brother, and I opened a restaurant.

There was no formal strategy in it. We were young enough to think a recession was a normal amount of difficulty, and we wanted to. We called it Luc Lac.

Meanwhile, at that exact moment, design was going through a renaissance and the industry was deciding, all at once and everywhere, that designers should be able to code. It was a genuinely new idea, and few could do both, because the two things had been taught in separate buildings by people who did not care for each other.

And there I was. Fifteen years old in a bedroom, pushing CSS into a Xanga page for no reason whatsoever.

I had spent a decade accidentally training for a job that didn't exist yet.

One of the agencies I'd interned at called. They needed a designer who could code. I'd stayed friends with their creative team after the internship ended, which is honestly the entire story. I came in, showed my portfolio, and they hired me. It was one of the best jobs I ever had.

They called me a Digital Art Director. They had to invent the title. That's how new it was.

The list

Fifteen years later, and I can fit my entire career into a paragraph, which is either efficient or a little sad.

An accelerator called Upstart Labs, where I led design for more than thirty startups and got the first ninety days of a company over and over until I could read an idea before anyone had decided what it was. Then out on my own, a one man design army. Projects at Intel and Comcast I still can't talk about. Nike Training Club, the running app, a campaign called Your Year, and the founding design team for SNKRS. Recruited by the SpaceX UX team to lead the visual UI on the first touch interface for Dragon v2, now called Crew Dragon. Then adidas, leading interface design on a women's training app. Then crypto, because my brother had been mining Bitcoin since the early 2010s and would not shut up about it, correctly as it turns out. A company called Interchange, where I built the best design system of my life, and where Kraken bought us two years in. Director of Product Design at Kraken, four designers to nearly forty, research team from scratch, hands on every surface we shipped. Then employee number one at XMTP Labs for four and a half years, embedded inside Coinbase, MetaMask, Zora, and World.

Somewhere in there I had two kids, got divorced, and got thoroughly burned out more times than I can count. That's a different essay.

A photograph of a shoe wrecked me in third grade. Twenty years later I was on the founding design team of the app people use to buy the actual shoes.

I went looking through my old Tumblr recently and found a post from April 2013, written a year into the accelerator job, by a version of me who had no idea any of the above was coming.

I don't know where I'll be next year but this past year has been one of the best years of my career.

I signed off on that post, and I am quoting this exactly, "You are the gas to my rocket ship."

I didn't know about Nike. Or SpaceX, or the acquisition, or the protocol, or the second kid. I just knew I liked where I was and had no idea what came next, which turns out to be the correct amount to know.

Side quests

Here's what the engine runs on.

The difference isn't importance, and it isn't who came up with it. Some of the best work of my life was the main quest, at companies where nobody handed me anything and the entire job was figuring out what we were building in the first place.

The difference is expectation. The main quest is the thing people are waiting on. There's a scoreboard and somebody is looking at it. The side quest is the thing nobody would notice if you dropped it tomorrow, which is exactly what makes it the only place you can chase a hunch that might not pay off for ten years, or ever.

The side quest is where you learn something before anybody is teaching it. Nobody could have told me at twelve that recoloring sneakers in a basketball game was job training, because the job didn't exist yet. Side quests look like wasted time right up until they're the only reason you're in the room.

You can't be self-taught without them. That isn't a coincidence, it's the definition. The side quests are the curriculum.

Then there's Luc Lac.

It's still open. Fifteen years later it's one of the three most reviewed restaurants in Portland, and it has outlasted nearly all of the rest of it. The accelerator wound down. Companies I helped build got acquired or quietly stopped existing. The restaurant is still there, full, on a Tuesday.

I filed that one as unrelated for years. There's no software in it. It never taught me a thing about a single tool I use.

But I wasn't in it because I could cook. I was in it because I had a read. I knew what people liked, what a room should feel like, what was about to be cool and what was already over. That was the entire contribution.

Which, it turns out, is the actual job.

Not Photoshop. Photoshop was just the thing I grabbed because the shoes were wrong. The tools have never stopped changing on me. Dreamweaver, Xanga, Sketch, Figma, a dining room, and now a room full of cards. The surface underneath has never changed once.

There's a line from John Maeda I bookmarked when I was 26 and reread for years:

Especially in our industry I'm confident to say that if you're good, passionate and crazy enough you can do whatever you want without having a bit of traditional education.

By then I was already working. Already hired, already shipping. And I was still out there collecting permission slips.

Nobody teaches the part that matters. Not to anyone. The MFA people got the vocabulary and the fundamentals, and those are real, and I wish I had them. I have sat in rooms full of them feeling like I busted in through the wall like the Kool-Aid man. But the read? The thing that tells you this is right and that is wrong and you can't fully explain why yet? Everybody who has it got it the same way I did. By being eight years old and unable to leave one thing alone.

The latest one

So I've stopped asking what a side quest is for. That question is the main quest talking.

The Alley is a side quest.

Not long ago some friends and I looked at each other and realized we had all the ingredients to open a card shop. We opened it in July, in Lake Oswego. Collin, me, and Collin's brother (and NBA Champion, 3x All-Star, 2x Olympic Gold Medalist) Kevin behind it.

Selling cards isn't what I do for a living. I still design all day. But it's the same move I've been running since middle school, and I quit fighting it a long time ago.

The thing that started me was a photograph. A printed picture of something beautiful that I wanted and could not have, on a page, that I stared at until it went soft.

Which is a trading card. That is precisely what a trading card is.

So on a Saturday afternoon, I stand behind the register and watch somebody pull the card they've been chasing for a year.

Sooner or later some kid is going to come in and get stuck on something. Might be the card. Might be the shoes in the photo on the card.

I hope somebody gives him a computer.