Apple: A Romance

If I ever write a memoir (and let me tell you, I plan to--I've got way too many great stories just begging to be told), I think the Summer of 2003 will almost certainly be its turning point.  It was in August of 2003, you see, that I fulfilled a longtime dream: I left Denver (my birthplace and home of 26 years) for California, started a job at Apple Computer (as it was then known), and set about reinventing myself. 

In many ways, my life had been leading to that point.  As a child I was profoundly impressed by an educational game called Robot Odyssey that I played on my friend's Apple IIc, and with a demo of Bill Atkinson's early Macintosh program Hypercard that my dad and I watched on television.  As a college student I was inspired by the quixotic, charismatic portrayal of Steve Jobs in Pirates of Silicon Valley.  And as a chronically bored Java developer in the Denver financial world I pined for the Silicon Valley of The Second Coming of Steve Jobs.  I spent almost every night after work building the most impressive Mac application I could and raising my profile through my Mac development weblog in order to get the attention of the high priests in Cupertino.  Eventually it worked--I finally got an interview with my first boss at Apple during Worldwide Developer's Conference in June of 2003, was hired in July, and was living in the Bay Area by August.

To say this changed my life is an understatement.  Where I had spent most of my first year out of college only sporadically employed (thanks to the dotcom bust and ensuing recession) and frequently wondering if I'd ever work in the tech industry again, now I was suddenly working for one of the most admired and innovative tech companies in the world.  Where my previous job had mostly involved working on in-house financial applications that I couldn't care less about personally, now I was directly involved in creating products I used passionately every day.  Where I had once been a fan, I was now an insider.

My life changed profoundly in other ways as well.  I had become frustrated with the insularity of my life as a shy kid in Denver, where I mostly socialized with a small group of my high school friends, and the difficult experience of looking for a job after college taught me the value of connections.  When California offered me the opportunity to reinvent myself, I determined that I would force myself out my shell, and for a time I made a point of turning down no social invitation.  Many of the people who grilled me so terrifyingly in my all day interview at Apple became a sort of surrogate family--taking me kayaking in Monterey, initiating me in the natural wonders of Northern California, helping me shed 20 pounds, inviting me to parties and other social events, introducing me to an ever wider circle of people, and becoming my roommates when I got up the nerve to make the once unthinkable move to San Francisco.

Needless to say, these were magical, transformative, romantic years of my life, and for a time I simply could not imagine myself ever wanting to leave Apple.  It had provided me with so much more than a livelihood: it had provided me with a life.

As with any whirlwind romance, though, the honeymoon couldn't last forever.  Apple may be a very special company, but it's still just that: a company.  And, like any company, at the end of day it needs to take care of business.  In Apple's case (or at least the part of Apple I worked in), that business is shipping amazing software on impossible schedules with astonishingly small teams.  It's been Apple's business since the "90 Hours a Week and Loving It!" days of the original Mac team, and the grand tradition continues to the present day (just ask anyone on the iPhone team how much vacation they've had in the last year).

Like the Macintosh team of old, I started out at Apple as a young engineer willing to subordinate my life (for a time) to something I was passionate about.  When I left my first position at Apple (in OS X Integration) for a real engineering job in Pro Apps, I was eager to make the features I was assigned the best they could be, even if it meant putting in difficult hours to get them done on schedule.  So I put in the hours.  I worked evenings and weekends.  I worked while I was ill.  Even when I ended up laid up at home in the throes of what turned out to be mononucleosis (a condition, for those who haven't had the pleasure, that lends itself more to constant unconsciousness than constant concentration), I sat in bed fixing bugs.  And little by little, I burnt myself out.

But it wasn't just the workload.  As the stress and hours increased at work, my 45 minute commute down 280, which I had initially thought of as a reasonable (even pleasant and scenic) drive, became a soul crushing daily slog.  With most of my social life in San Francisco, but my demanding job an exhausting drive away in Cupertino, I started finding it harder and harder to keep up relationships.  As a recent article about commuting in The New Yorker put it:

“I was shocked to find how robust a predictor of social isolation commuting is,” Robert Putnam, a Harvard political scientist, told me. (Putnam wrote the best-seller “Bowling Alone,” about the disintegration of American civic life.) “There’s a simple rule of thumb: Every ten minutes of commuting results in ten per cent fewer social connections. Commuting is connected to social isolation, which causes unhappiness.”

Perhaps most importantly of all, though, I began to feel more and more that my job at Apple, once a source of such growth, was now holding me back creatively.  The natural curiousity, drive, and entreprenurial spirit that had once led me to develop two significant Mac applications, write a widely read weblog, and explore a variety of experimental side projects, had been all but crushed under the weight of a gigantic bug queue and long commute.  My well respected side projects were rapidly turning into abandonware, and my once compelling web profile had been reduced to a trickle of Twitter and Flickr posts.

Still, my attachment to Apple was so strong that it was going to take a lot to convince me to leave.  It took the encouragement of a number of good friends (who I plan to thank in another post) and, fittingly, the advice of Apple's two founders to convince me it was time. 

First, while driving home one night, I happened to turn on NPR and hear an interview with Steve Wozniak on the locally produced show "City Arts and Lectures" (I can't find audio or a transcript on the web, sadly).  In it, Woz told the lesser known story of Apple's founding from his perspective, and one part of his account in particular caught my attention: how hard it was for him to leave Hewlett Packard to start Apple.  Unlike Jobs, Woz didn't take Apple that seriously in the beginning, and hadn't planned to leave his beloved job at HP at all until the venture capitalist providing them seed money made it a condition of funding.   Woz loved HP, a company created by engineers for engineers, just as much as I loved Apple, and for a time he felt that it was where he'd spend his entire life.  It took a great deal of prodding by friends to convince him that it was worth leaving a prestigious job working on products he so dearly admired (in this case the HP graphing calculator) to pursue some wild eyed venture with Steve Jobs.  In the end, of course, the risk was more than worth it.

Second, I kept thinking back to Steve Jobs' inspirational 2005 Stanford commencement address, and in particular the part where he talks about how he decides whether his life is on the right course:

When I was 17, I read a quote that went something like: "If you live each day as if it was your last, someday you'll most certainly be right." It made an impression on me, and since then, for the past 33 years, I have looked in the mirror every morning and asked myself: "If today were the last day of my life, would I want to do what I am about to do today?" And whenever the answer has been "No" for too many days in a row, I know I need to change something.

For me, that answer had definitely been "no" for too many days in a row, and with the project I'd been working on wrapping up (it was announced, to a very positive reception, last Sunday at the National Association of Broadcasters show in Las Vegas) I decided it was time to take the plunge and try my hand at a new venture (more on this later).  My last day was Friday, April 13, 2007 (hopefully not an ill omen for either me or Apple!).

I will always look back very fondly on my time at Apple, and I'm forever indebted to the friends there who gave me my big chance, took me under their wing, and taught me so much.  Apple remains, in my mind, a very special place, and I consider it a distinct honor to have been there during a large part of what might be called the company's "Silver Age."  I expect Apple will continue to amaze and delight us for years to come (the iPhone is a tantalizing start), and I'm looking forward to experiencing the excitement of its surprises as an outsider once again.  And who knows--as one of my bosses there was fond of saying: "The question's really not how long have you worked for Apple--it's how many times."  I wouldn't be at all surprised to find myself back in the halls of 1 Infinite Loop someday.