One Infinite Loop: From Johnny Castaway to Steve Jobs

Help! I stumbled my way into Design and now I can't get out

I’ve spent most of my life thinking of myself as a designer of some sort. I arrived at that label when I was about sixteen years old. At the time (almost twenty years ago), being a designer didn’t have the connotation that it has today. There were just fewer points of reference. Nobody knew (or cared) who “designed” the world around us. I certainly didn’t. My calculus was simple: I had an affinity for computers (mostly video games) and liked to draw.

I have Pepe to thank for my love for computers. Pepe was a family friend. A Cuban, like us, who “knew computers”. Back then, “knowing computers” was similar to knowing “cars” or “sewing machines”; just another trade we would barter as we learned to assimilate as immigrants. One day, when I was about nine years old, Pepe showed up at our house with a computer. The computer wasn’t one of those cool see-through Macs that people post nostalgically on Twitter today. In fact, it wasn’t anything at all. It was a beige box made out of discarded parts from better computers. To us —a Cuban family starting to make sense of Costa Rica— a computer was emblematic of progress. Like the obelisk in the beginning of 2001 A Space Odyssey, we looked at the computer like alien technology. Being an alien myself, I became enamored with it.

Pepe pre-installed a few essentials into that computer for us. He bootlegged copies of Sierra’s Outpost (a game far too complex for my 9-year-old mind to understand), Lotus, Prince of Persia, and Doom. I played every game religiously, but my favorite part of owning a computer was the screensaver. Among the classics that came pre-installed with Windows 95, Pepe included a gem that I later learned was called Johnny Castaway. If you’re not familiar with this storytelling masterpiece, this screensaver featured a castaway named —you guessed it— Johnny, who improvised different scenes at random. I found this so unbelievably compelling that I often times would watch each scene like an episode of Friends. I’d grab a snack (saltine crackers, cream cheese, and a cold Coca-Cola), lean back, and watch each scene play out over and over again, hoping to catch a new one.

I became so obsessed with computers that my dad —a Cuban immigrant trying to make sense of the new world— deemed it as an addiction. He became so concerned about my interest in Johnny that he would leave for work and take with him the power strip that connected all the spare parts of my Frankenstein computer.

As I got older, I tried to fit computers into my daily life as much as possible. When it came time to pick a career, I chose graphic design. At the time, I didn’t have the hubris to think I could make computer programs but I did know I wanted to use computers for a living. As a graphic designer, I used computers, sure, but I designed physical media. Over time that evolved to digital media, then digital tools, and somewhere along the line that became synonymous with “culture”. Or at least that was my hope: I wanted to design culture.

During that time, I was also forming myself, my world view, and how I fit in within it. That journey was heavily influenced by my experience as a twice-over immigrant; first as a kid in Costa Rica, then as a teenager in the US. I struggled to belong in a world that constantly treated me as an outsider. Rather than respecting and admiring how the world worked, I began to scrutinize the systems and institutions that governed it. The status quo was a wild horse to be tamed as I galloped to my destination.

Among those institutions was the corporate force. The beating drum for the American dream. As soon as I was old enough to get a job, I got too many jobs. I was too young to storm into Ross looking for a business casual shirt I could tuck into my khakis pants. Nevertheless I wore the uniform at call centers, data entry companies, and collection agencies. I was the voice on the other line waiting for you to say “can I talk to your manager?”

In order to fund my incomprehensibly expensive design education, I spent hours working in cubicles, and in my spare time, I watched movies about how pathetic it is to work in cubicles. During my lunch breaks, I read Dilbert while scrambling change to afford a snack from the vending machine. At night, I played with my band in decrepit bars, inhaling second-hand smoke for dinner. My heroes weren’t businessmen, they were the jesters that made them uncomfortable.

Then, the iPhone was announced.

I knew of Apple, of course. Before the iPhone there was the iPod, and in between there were a series of impossibly expensive and increasingly thin computers that I admired from afar. I was introduced to the Mac during my first graphic design class. It was presented to us as a design tool, not a personal computer. I had my Frankenstein PC at home, but the Mac was the professional tool that I used to create things. It was a strange concept: a computer as an object of desire.

There was altruism inscribed in it and it worked just slightly differently than anything I was used to. The start menu was at the top, not bottom. The mouse had only one button, not three. The minimize button was on the left, not the right. It was glossy and fluid and it behaved like a video game: installing applications was as simple as dragging an icon from one window to another. Want to uninstall them? Just delete it and it’s gone.

Apple started taking over culture in front of my eyes. The iPod, which came out in 2001, harkened back to the Space Odyssey’s monolith. It was so opinionated that it once again captivated me with the allure of alien technology. Paired with the devices were the commercials. Two anthropomorphized operating systems against a white background described Apple as the antidote to the oppressive corporate world.

Behind it all, there was a guy named Steve who seemed to be getting away with the impossible! He used the stage like the jesters I admired. He quoted Bob Dylan and hosted other jesters musicians on stage bookending his corporate announcements. He introduced me to an anti-corporate corporation. Through Steve, I learned about the myth of Silicon Valley: barefooted twenty somethings in hoodies and jeans disrupting the corporations that seemed to rule the world while swimming in ball pits and ping pong tables. It was seductive, it was subversive.

So, I —a forming designer trying to “design culture”— set my sights into this as a way to fit into the world. Finally, a system made of outsiders, waiting for my arrival.

I poured my life into that pursuit and in doing so, missed its transformation into the same corporate system I was trying to escape. The cubicles became open floor offices and the vending machines transformed into ball pits. Somehow the hoodie-wearing twenty somethings now occupy the same space as the suit-wearing square in the Apple commercial. Villainous and aloof all at once, they’ve become the antagonist we all root against.

What the fuck happened? Well, twenty years happened. I suppose nothing can remain the same for twenty years.

For a while there it felt like we were riding the wave. It seems almost impossible to imagine now, but there was a time when I earnestly believed the world could change for the better. I’m not entirely sure whether it was the fact that I was in my twenties or whether the world was actually less cynical. I wonder if this is exactly how they expected it would play out or if something went insidiously wrong somewhere along the way.

Regardless, it’s now twenty years later and I still call myself a designer. My relationship to design, technology, and the world has shifted dramatically (who hasn’t?!) but the label remains the same. It’s convenient. It’s a way to paint order into an otherwise exhaustingly chaotic world.

The context is entirely different, yet the label is the same. Along the way, there have been different prefixes attached to the label: senior, lead, staff designer. Sometimes other suffixes are attached to the label: design manager, director. All of those descriptors exist to place me, and people like me, in a corporate system.

It’s easy to get lost behind the path ahead painted by these labels. And how could I not?! The system is designed around this. There are literally levels for you to grow into over time. You start out as a level 3 (nobody wants to be a level 1) and level up over time. Don’t worry, if you get too close to the top, new levels get added all the time.

As you reach the higher levels of this corporate RPG game, you’re presented with a choice: management. To the managed, Management is presented as a supportive role: nobody wants to be managed but everyone wants to be supported. To the managers, Management is presented as a leadership role: nobody wants to manage but everyone wants to lead. Ultimately management is about enforcing the chain of command.

Countless people before me (and after) have struggled with this choice. I’ve learned that it comes down to your ability to respect and admire the status quo of the system you’re a part of. As for me, I’ve fallen prey to the allure of management many times before.

The infinite loop goes something like this:

1. Join a small team, the underdog, the disruptor. I thrive here, I push the team forward.

2. There’s a vacuum for leadership. Nobody asks me to fill that vacuum but I somehow position myself as the leader. Leadership at that stage is fun; lots of works to do, hats to wear.

3. Team grows, more leaders arrive. Because nobody asked for my leadership in the first place, I am not considered a peer amongst new leadership

4. The role of leadership changes; it’s no longer about wearing multiple hats. It’s now about delegating and scaling the team. Leaders focus on respecting and enforcing the chain of command, talking to other leaders, making moves to retain leadership.

5. I become disillusioned with leadership and current team. Go back to step 1

Each loop feels unique (this time will be different!) and in some ways it is. As I get older, I’ve changed the way I perceive the loop. Even though it’s the same, it means something different each time around.

Sometimes I wonder if I should break from that loop. I see other seemingly happier people who surrender themselves to it and swim along the corporate flow. That feels simpler and if there’s one thing I’ve learned after designing for twenty years is that: simple is better.

Lately I’ve been practicing how to be simpler and treat the loop like that tamable horse to gallop to my destination. The key, I suppose, is to find a new destination.

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