Miles Traveled

”Look daddy, I’m touching the wind!”

We were driving upstate, the windows down and summer’s last breath was traveling through the back seats. I shared the car with the usual suspects: my wife and children. I looked through the rear view mirror and saw my older son, reaching his hand out the window. He can’t believe how fast we’re going. I can’t believe how fast he’s growing.

—

I’m getting to that age where you spend more time thinking about the past than the future. For me, that takes the shape of cataloguing what I’ve done.

I recently added a section to my website that tries to describe all I’ve done, along with controls to customize how verbose you want it to be. In that exercise, I realized I was 15 when I first got a pirated copy of Photoshop and Illustrator. I’m 38 now. That’s 23 years of pixel pushing. I think that counts as a career.

One thing that became clear is an implicit principle I’ve used to make career decisions, since the beginning: optimize for new experiences.

That principle has taken me from a living room in Costa Rica, an art school classroom in Tampa, a small startup in LA, a big tech campus in SF, business flights to London, speaker stages in Seoul, research labs in Seattle, conference rooms in DC, and now this windy car ride in upstate NY.

The example that comes to mind is very silly.

When I joined Facebook in 2013, it was customary for designers to go through a 2-week onboarding they dubbed “Design Corps” (later renamed to “Design Camp” when they replaced the military motifs with outdoorsy visuals, much more palatable to larger audiences). During these 2 weeks, you’d spend most of your time sitting in a room, listening to hordes of Facebook employees talk at you about their teams. The goal was to download as much context as possible to get you ramped up quickly. I remember it being incredibly inspiring and well run.

Make no mistake: joining Facebook was by far my biggest accomplishment at the time. The only time I’ve seen my father cry is when I called him and said I’d gotten an offer from the company. I had ventured to the west on my own a couple years earlier and just 6 months before that call, he visited me in SF and we drove around touring the parking lots of iconic campuses like Stanford, Apple, and Facebook. So, badging into Facebook as an employee was nothing short of surreal.

Design Corps culminated with each designer picking a team they wanted to join. There were a couple teams that had open headcount when I joined: Pages, Search, and Messenger. I had met with all of them and agonized over the choice for two weeks.

Search just had a new VP of product join their org, I forget his name, but for some reason he wanted to meet me. The meeting was not a typical meeting I had come to expect. We didn’t sit in a room with a table between us. Instead we walked, nay sprinted, around the campus as he shouted his vision for the team under the oppressive Menlo Park Sun. I was both out of breath and dumbfounded by the end of it. I thought “is this what meeting at Facebook is like?!” Turns out yes and no. They love to “walk and talk” over there.

Pages was also going through some changes. They described it as “a vacuum of design leadership” and presented it as an opportunity. Result between the lines gave me the impression that this was the team I should join if I was serious about making an impact at Facebook. “Impact”, as I came to learn, was the company’s currency. The product was shoved in the company’s least popular org amongst designers: Ads. It was all about business outcomes, while the rest of the company felt like a playground where the real world changing was done (both turned out to be catastrophic in terms of outcomes). To entice designers to join, they had heavily invested in their swag. It wasn’t a typical hoodie and American Apparel t-shirt. They commissioned a green canvas jacket with custom made patches. The tech equivalent of varsity jackets. To top it all, their own VP of product took me out to dinner at one of the company‘s Mexican restaurants in campus and walked me through his vision for the team, this team with a table between us. He was seemingly just a PM at the time, his nickname was “Boz” and he’s now the CTO.

Messenger was the sexy team. They had just launched Messenger 3, a standalone app that was prototyped using Quartz Composer, and felt like a glimpse into the future of interaction design. They had nothing but superstars on their team. They all seemed to be best friends and enlightened in ways that I could only imagine. One rainy day, I was rushing between buildings and saw Mac, one of their designers who unapologetically claimed to be the best designer in the company (I think he was 21), standing outside under the rain.

“Are you okay?” I asked.

He looked at me, and said “I really like the rain”

I kept running to my next meeting.

By the end of the second week, I’d made my choice. I was going to be Pages’ newest designer. Partly because I thought I had to, but mostly because I wanted that jacket.

Honestly, I didn’t follow any smart decision matrix to make that choice. I just wanted the jacket and the room to have more scope for “impact”. In retrospect, Search or Messenger were a better fit, but not the experience I was looking for.

At Pages, I got to partner with Boz and design his presentation slides for one of the team all hands — that’s where I noticed that he scripted every single word, including the pauses and the “uhms”. I was part of Margaret’s “trusted group” where she had us give feedback on her TED talk. And made friends I still wish happy birthday to this day.

The jacket was a conduit to an experience I cherished. From there, there were many more proverbial jackets that invited me to move across continents, strap cutting edge technology to my face, and ultimately leave Facebook and find other experiences I couldn’t find within it.

I now find myself a decade later recounting all the jackets I wore and feel grateful I had the chance to try them on. The chance to go wide and step outside what’s comfortable. The chance to pick new experiences, not because they were the right ones, but simply because they were new. Novelty not as a dopamine shot but a chaperone to alternate realities.