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Top 4 Lessons From a Former Apple Engineer

I’m a New Yorker. Raised in Greenwich Village, my brother and I are biracial Village kids. My dad is African American, and my mom is a Russian Jew. My dad left when I was 2 years old, and I never saw him again. “Leaning In” does not begin to describe the miracle my mom pulled off raising my brother and me. She always got it done.

I call New York my second parent. While my mom fed us, NYC fueled my voracious curiosity and hyperactivity. The quirky, oddball people. The sounds: Salsa. Rap. Rock. Metal. The unending babble of street life. Sometimes: “Yo, my young brutha, can I talk to you for a minute?” Sometimes: “You want me to pay how much for that mashugana schmatta?!” I was good at basketball. When I wasn’t shooting hoops, I spent a lot of time hanging out and exploring the streets of the city, frequenting the Whitney and the neighborhood’s used bookstores.

I graduated from college with B.S. in Mechanical Engineering, but after a series of rather boring engineering jobs futzing around with spreadsheets to make routine calculations, I decided I wasn’t feeling the whole engineering thing. I took an evening programming class at New York University, and my inner geek began to stir. I remember learning the material and feeling like the entire course of my professional life was about to change, and it did. Here are a few things I learned along the way:

Lesson no. 1: Chutzpah and cluelessness can take you a long way.

After completing the NYU course, I quit my day job and wangled a job interview with a New Jersey defense contractor looking for programmers. Using a strategy that I can still only describe as “clueless chutzpah,” I walked into the interview, opened my briefcase, and pulled out the source code listing for a dopey computer game I’d written as a class project. I proceeded to wave it in front of my interviewer’s face, pointing animatedly at lines of code and yammering about how cool it was. All in a deranged attempt to distract my interviewer from the blindingly obvious fact that I had zero actual programming experience. Hey – it worked! I got the job.

Always show up. Tell a good story and swing for the fences. Americans seem to love passion, energy, and hustle. We’re suckers for a good story. It is in our DNA. It’s the American way.

Lesson no. 2: Find – and work with – people who challenge you.

Once I landed that first programming job, things began to accelerate. I read an article about computer graphics and learned about the amazing research happening at the University of North Carolina at Chapel Hill, where I went for my Master’s in Computer Science. As graduation rolled around, Apple invited some of us out to Cupertino for interviews. Mind you this was the pre-iPhone era. Upon arriving at the San Jose Airport, I was met by a uniformed driver. He ushered me into the back of a black stretch limo to take me to the Apple office. No joke. I plopped down next to two other slightly bewildered computer geeks, all of us with the same goofy “oh, hell yah” smile on our faces. At risk of sounding like a jerk, I’m going to say it like it was: My interview process was a breeze, and the offer letter soon arrived in the mail. I was headed to Silicon Valley.

At Apple, where I became a researcher in the Advanced Technology Group, a door opened. I had stepped into a world densely populated with smart, passionate, driven people. Their skills were best-in-class across a range of disciplines that interested me – from computer graphics and video to audio and human-computer interaction.

We talk about Silicon Valley today being a very non-diverse place. But in many ways, my own experience there exposed me to a lot. If you surround yourself with people from a wide range of backgrounds and interests but a common excitement and vision, there’s a certain openness and generosity that reveals itself – a “Hey, check out this cool thing I’m working on!” that is too often lacking in other people.

At Apple, my team’s collective concern — never verbalized but deeply held — was to humanize computer technology. We did not seek to “push or disrupt the technology envelope,” as every other tech company doggedly flogs itself to do. Rather, our approach was to think hard about what we could do to make technology disappear.

Lesson no. 3: Just because you’re the only one who sees something doesn’t mean it’s not there.

The final project I worked on at Apple turned out to be hugely important for my career. I was invited to join the QuickTime VR product team, which sought to capture the world via photography and map it in a digital form. Back then, it was still a CD-ROM. Remember, this was during the early days of Web browsers. Google did not exist, and Netscape was king of the hill.

One afternoon while noodling around with Netscape, it dawned on me that QTVR would be an amazing Web product. The idea exploded into my brain fully formed. Boom. People would be able to distribute 3D panoramas around the world via the Web. I couldn’t wait to tell my team my brilliant idea. Their response? Meh. “Dude, QTVR is a hot CD-ROM product. Web shmeb …”

I spent the next 50 days racing to adapt QTVR to a browser extension — one of the first — creating artwork and content for a website I built from scratch. Gradually, the team and other Apple folks saw the light, and QTVR for the Web took off. It won industry awards the year it launched and paved the way for Google Street View. Perhaps best of all, it gave me bulletproof credibility at Apple.

Lesson no. 4: Scare yourself.

I stayed on at Apple for eight years, eventually switching to a consultant role before leaving to embark on my solo career. At the time, it was scary. But sometimes you just have to hang your butt out over the edge and do the thing only your eyes can see. Fear can be a chronic illness – this thing you have to manage and address. I always tell people to start by finding something they don’t think they can do but that they care about a lot. Then start taking small steps and building confidence.

Expect to hear “no.” A lot. From your boss, peers, family. Mostly from yourself. Acknowledge the no. Welcome the no. Then tell “no” to step to the left because you need to get back on your grind.

Cross-posted from The Well at Jopwell.

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