Apple

January 22, 2023

When I knew I wanted to move back to the Bay Area, I told the guys at the Iconfactory. They deserved to know what my plans were as soon as I did. I started to coordinate interviews at Apple. The first one was with the Human Interface design team. (I remember referring to them as “Platform.”) This was the team responsible for OS X, iPhoneOS, and iPadOS. They designed the system.

At the time, the HI team operated out of IL2 (2 Infinite Loop). I arrived on February 25, 2010. Early, I stopped by the Company Store. There were a lot of tourists outside. (I was kind of a tourist, too.)

HI Interview

I only remember two things from this interview:

  1. I presented my portfolio uninterrupted, in their dimly-lit studio.
  2. At the end of the presentation, a designer named Imran Chaudhri leaned back in his chair and asked me: “What is design?”

I struggle to identify what exactly about this question sounded tactless to me. Maybe after all the consideration, time, and effort that got us to this moment, to get everyone in the same room, to sit through my presentation, then ask me what I think design is? Was my portfolio not exemplary of what I thought design was?

I answered in a pretty snarky way: “Don’t you already know?”

I presume my response was at least one reason I didn’t get the job. The Apple recruiter relayed pretty quickly (within 10 minutes of exiting) that the HI team wasn’t for me and that she’s got a few other ideas. I flew back to Greensboro before flying out again in March.

Interlude

Since the folks at the Iconfactory knew about my interview travel, they let me in on a little secret: Craig Hockenberry was invited by Apple to go test Twitterrific on an actual iPad before its release. Their idea was for me to pop in and help before and after my interview.

That morning, we went down to the hotel lobby and had some breakfast. Every couple minutes, new familiar faces showed up in the lobby. More developers. Someone finally spoke up, “Are you here for the—?” Everyone nodded their heads subtly.

We compared notes on when and where to meet our Apple rep. Some of us were told to meet in slightly different locations and at slightly different times. We didn’t know if this was a mistake or not, so we all kinda headed over together. When we got there, you could see the look of panic on the Apple representative’s face. What did they expect when they put all these developers in the same hotel?

Consumer Apps Interview

Later, in a more brightly-lit conference room, I met with visual designers from Consumer Apps (iLife + iTunes): Tim Martin, Kellie Albert, Matt Evans, and Brian Frick (remote). I gave an identical presentation as I did with the HI team, but within one minute, Brian chimed in from his video chat on a laptop perched nearby. The slide was a stylized map of the United States. Brian asked, “Is that ...a World of Warcraft map?”

Off to a good start. These people get me. After my presentation, I met with Bill Bachman, the design director. In a very small room that could only fit a table and two chairs, he asked me how I would approach designing a new icon for iTunes. I loved this question.

I began talking, working my way through this problem. iTunes was not just about music, there were movies and TV shows and podcasts and— could the icon really be a CD anymore? Should it even be music notes anymore? What if you played off of “multimedia” more, with music notes on a film strip? After about 10 minutes of rambling, I realized— oh shit, what if I shouldn’t have verbalized every word I was thinking? I nervously asked, “Am I answering your question?”

Tim (the design manager) took me to get pizza at Caffè Macs and talk more. I liked this team a lot. I flew home, and received an offer on March 31.

Before I left the Iconfactory, I made one last icon set: Infinite Loop.

iTunes

When I started, Kellie was asked to share her office with me. I tried to be as small as I could in her space (even with two displays). I don’t know if I had anything of my own in there except my OS X Panther mousepad.

One day in June, Kellie and I were sitting on the patio eating lunch when she took a photo of me with my iPhone. Sitting right behind me was Steve and Jony.

Actually, I saw Steve around campus a lot. He and I seemed to arrive and leave at the same time, and we worked in the same building. More than a few times, we held the door for each other.


As per a request from Steve, a few of us started working on new concepts for an iTunes icon. I was excited, but nervous. I was not the first person to try to make a new iTunes icon. There were lots of really, really nice icons that Brian made before I ever got there.

One of mine was circular, with a thin white border (like the old Dashboard icon), a purple and green lens flare background (similar to the AppleTV branding at the time), and a black music note centered in that circle.

And that’s the one he chose.

After that, I made several more for Keynote decks presented to our VP and emailed to Steve. A purple background (like the iTunes app on iPhone), and a blue background too. At one point, the blue was “not beautiful enough.” I was also thinking about the Remote app for iPhone, which had a play triangle. So I tried one of those too. For a little while there, it seemed like that was the icon we were going with. But after a few new music note outlines, he chose the one that shipped with iTunes 10.

Honestly, I don’t know if I ever felt more proud in my life.

Some people didn't like it. I tried to not let that bother me. The only approval I needed was Steve’s. I printed this comic and taped it to the front of my office door.

As part of this same release, I also redrew iTunes controls, like the playback buttons, LCD, and volume slider. I suggested making the “stoplight” window controls vertical, to eliminate the titlebar since that entire toolbar was grabbable. (Not everyone loved it, but Panic adopted this style for Coda!)

One day during the development of this release, Steve requested to remove all the icons from the sidebar because it was getting too busy. My heart sank. Icons are my life. How were were going to navigate such a long list without icons that hint at the type of list item? In a last-ditch effort to save icons in the sidebar, I created shaded monochrome icons for the source list, and Steve approved them. This style of icon inadvertently became the de facto style of sidebar icons on a system level for the next decade.

Part of what was so appealing to me about this job is that there were so many apps to work on. iBooks, Trailers, and Remote fell into the iTunes apps bucket.

For iBooks, I designed the visuals for highlighting, bookmarking, and annotating. I think these are the first of my features that shipped (June 7, 2010), personally approved by Steve. I even proposed using Apple Casual in place of Marker Felt, which also shipped! (However, when it went public, some people mistook it for Comic Sans, and it was later replaced.)

For Trailers, I was responsible for the UI and visual design for this app made with Alan Cannistraro. I also got to make another app icon, with rich visual detail. The Remote app also fell into this org’s responsibilities, and while I worked on the app itself minimally, I did create a new Remote app icon to match the new iTunes 10 icon. This one used the “play triangle” mentioned earlier.

iLife

iPhoto, iMovie, and GarageBand were referred to collectively as iLife. These were kind of in a separate (but related) corporate structure, with its own VP. Some designers on my team worked only on iLife apps. Some worked only on iTunes apps. I got to work on both.

For iPhoto, I dug through some DVDs of wood textures we had in the studio and designed some nice wood shelves for our physical iPhoto products. (When Steve saw them, he relayed to the iBooks team to switch to this design for their own shelves. When that happened, I also designed a new iBooks icon to match.) It also became the style for Newsstand. For iMovie, I helped design the project browser, which was a brick wall with movie posters and a theater marquee. I created the iMovie theater logo and surrounding neon, which engineers cleverly made flicker on when you launched the app.

But I probably had the most fun with GarageBand. My friend Matt did most of the GarageBand visual design (and it’s probably the best artwork Apple ever shipped in an app), but there was a lot on his plate for the upcoming iPad app, including various instruments you could play full screen. So I helped by designing a few guitars and the B-3 organ interface, which I’m very proud of. Someone on the team had one at home, and I asked them to take some reference photos without dusting it off or cleaning it up. I drew in some scratches on the wood, and tinted the keys. It became a hero image for that release. I also composed an app icon using the current GarageBand guitar and a brick background.

Etcetera

That was a lot to keep me busy, but I also made app icons for some lesser-known apps like iAd Builder and iBooks Proofer. For WWDC in 2011, I managed to convince the right people to let me make an app icon themed around Moscone West itself. I did other small stuff like making icons for new iPods in the iTunes source list. And I worked on some internal things. I got to prototype some conceptual UI ideas with Joe Howard (famous for the iBooks page curl interaction). I met brilliant designers like Mischa McLachlan and Johnnie Manzari and engineers like Elliott Harris. These are all people I would jump at the chance to work together again. And some, I would.

At some point, the iTunes and iLife orgs split, and designers who (like me) worked on both were assigned a side. For me, it was the iTunes side. The other visual designers were assigned the iLife side. I missed the opportunity to work on iLife apps like GarageBand, but I went deep on music, and looked to new and interesting ways to visualize music inside iTunes, some of which debuted in iTunes 11 (like the album split-view that grabbed major colors from the album art), which I wasn’t ultimately around to ship with the team.

I loved working at Apple. I loved the people. It was so fun to work on such high-profile things, but I think mostly I loved the amount of people committed to building great things. It was infectious. (Also, it was extremely cool to see hardware before the rest of the world did.)

But the one-hour-each-way commute started to hit me. The long bus rides were not fun, and I felt like a chunk of my day vanished to travel time. I wanted to work much closer to home, and a few old friends were encouraging me to consider a payment processing startup with an office downtown, just a few blocks from my apartment.