On the Road

At the end of one of my last days working for Apple, some co-workers and I met for drinks at Santana Row, in San Jose.  By this time, everyone knew I was leaving, so of course everyone was asking what I was going to do next.  I made some unenthusiastic noises about possibly working for a San Francisco startup that was trying very hard to recruit me, but I'm sure I didn't sound too convinced, because it wasn't too long before my friend Mike chimed in with "I know what I'd do if I were you."  When I asked what, he said: "I'd buy a Canon 5D, the 50mm 1.4 lens, and hit the road!"

Around the same time, I was IMing with my friend Sarah about my uncertain future plans, and, completely unprompted, she echoed Mike's sentiment that I should get some distance from San Francisco for awhile.  I think she felt (rightly) that it was the best way for me to get some perspective on my situation.

Now, both of these friends know me pretty well, and I'm sure they both knew that deep down, hitting the road was precisely what I wanted to do.  I had felt so constrained by my job for so long that by the time I quit, my spirit was, to paraphrase Led Zeppelin, crying for leaving.  Combine that with my lingering sense of personal and professional disillusionment toward the Bay Area, and a good, long break and change of scenery was pretty much the only way I was going to get my enthusiasm back.

So I told the starup I wouldn't be working for them (with the help of a little just-in-time confidence boost from my friends Mai and Courtney), bought the camera gear, and did exactly what Mike suggested.  Living mostly off income from my shareware app, PodWorks, I've since traveled extensively in California, Colorado, New Mexico, New York, New Jersey, Pennsylvania, Chicago, and Spain.  As anyone who has been following my Flickr stream has seen, I've had a pretty amazing run.  Among the highlights:

  • I hiked on spring snow with my Dad in Rocky Mountain National Park, Colorado.

  • I scaled the Great Sand Dunes in Southern Colorado.

  • I followed in Ansel Adams, Georgia O'Keefe, and Paul Strand's footsteps by taking sunset photographs of Mission San Francisco de Asis outside Taos, New Mexico.

  • I had my first kiss with a long-distance crush (now my girlfriend) by lamplight in Central Park, then spent a magical weekend in the art deco, Central Park West apartment of my dreams (all of which is such a good story that it merits a post of its own!).

  • I drank in some of the best bars New York City (and therefore the world) has to offer (including probably my all-time favorite, Milk & Honey).

  • I got excited about being an indie Mac developer again at Wolf Rentzsch's already-legendary C4 conference in Chicago, while enjoying the company of my brother Bobby and good friend Sarah.

  • I took my East Coast girlfriend on a tour of my favorite part of the West Coast–in a ridiculously souped-up Shelby Mustang convertible, no less.

  • I celebrated my 30th birthday in Barcelona and at a beautiful Mediterranean villa with two of my best friends.  We drank Estrella Damm by the pool and ate at some ridiculous restaurants.

  • I spent a week with my sweetie in one of the vanishing landmarks of New York Bohemian cool, the Chelsea Hotel, before the forces of gentrification could take it over completely.

Any one of those things would have been pretty amazing by itself, but I've done them all (and a lot more) in the time since I left Apple.  It's not too much of an exaggeration to say I feel as though I've squeezed a lifetime of experience into about six months.  I've traveled by plane, train, automobile, subway, foot, bus, and even a little bit of boat.  I've downed margaritas with an Aspen buddy of Hunter Thompson at the Taos Inn (he excused himself by saying "I've gotta go entertain these broads"), sipped cocktails with my girl in a Lower East Side speakeasy, savored cava in the finest restaurants of Catalonia, and knocked back beer while listening to working stiffs talk about unions in Chicago.  I've woken up in glass towers, seaside villas, quaint B&Bs, Japanese onsens, suburban houses, uptown apartments, kitschy Californian motels, and bohemian flophouses.  I've eaten green chile in Santa Fe, fried chicken in Washington Heights, sushi in Tribeca, and cold cherry soup with ginger in Girona.  I've stood by the side of a remote highway in Southern Colorado listening to the mournful sound of coyotes yelping in the distance, dodged children playing in water from an open fire hydrant on a hot New York summer day, and watched as a dramatic rainstorm over the Mediterranean gave way to a eerily calm moonlit night.

In total, I've spent probably 100 out of the 180 days since I've left Apple on the road.  And, while I've finally grown a bit travel weary of late and I've started thinking about where and how to settle down again, I've finally come home with a renewed enthusiasm and entreprenurialism, and a realization that I've been priveleged to enjoy the kind of freedom in my travels that most people only dream of.  I may slow down for awhile, but you can bet I won't stay put for long.

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6 responses to “On the Road

  1. Following you on Twitter, it sounds like you've been having an amazing
    time. Honestly, I would be lying if I said I wasn't incredibly jealous!

    That's one thing I think most companies don't do well, and that's let
    people travel. Even with the generous number of vacation days here, I
    feel like I'm mostly spending mine seeing family in familiar places. Maybe I should think about working remote? Heh.

  2. So, so good. At the risk of sounding parental, I'm really proud of this decision of yours. Adventure takes extreme courage, and extreme life adjustment, but once you throw off that which is weighing you down, everything else changes for the better. I couldn't believe the New Buzz I met in August – only a faint trace of tired, uninspired Buzz remained. So this, this is good.

  3. I read your "Apple: A Romance" post some time ago and found it inspiring. I stumbled onto your latest post, "Interpreting Apple," and realized it was the same person. Very astute observations.
    With respect to "On The Road," I cannot believe that someone who had the financial means to do this had not done it already. But I suppose the drive that caused you to work yourself into a cinder is what allowed you to accumulate those means to begin with.
    And man, your girlfriend is cute!
    Keep up the posts. Some of us are living quite vicariously through you.

  4. They are really wonderful photos, and I'm really happy you've shared them with us here and on flickr. Good luck on your future journeys!

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