Albert Einstein, Bill Gates… and Me

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In 7th grade, my parents told me I was adopted by my dad, meaning the man I knew as my dad up to that point was not my biological dad.  My reaction was to put in our VHS copy of Look Who’s Talking. Movies were a language for me from an early age. When Kirstie Alley softens her heart to John Travolta at the end and lets him essentially become the talking baby’s father, I realized that the dad I knew was my dad, and this new information actually didn’t matter at all.  It never upset me again.

The movie Goodwill Hunting came out in 1997 when I was a senior in high school—and it blew my mind.  As I remember it, I was the most charming guy in school and everyone — my fellow students, my teachers, the school’s administrators, local politicians– just adored me.  As we all know, memory is 100% accurate so you will have to take the previous sentence as concrete truth.   Goodwill Hunting was a Dead Poets Society drama bred with the crude comic stylings of a Kevin Smith movie.  It packed an emotional punch unlike anything I had experienced.  It reminded me of how connected to movies I was and how much I wanted to make them.

I will go off to a prestigious film school, I told myself, and I will take the movie-making world by storm!

Approximately three years later I dropped out of college. (read more…)

To The Woman Pouring Water In a Homeless Man’s Mouth

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To the woman pouring water into the homeless man’s mouth:

Hi, I work two blocks from you on Taylor Street and Golden Gate Avenue. Every morning I bike down Golden Gate to my office job in a co-working space. I ride the elevator seven floors to the “penthouse.” I brew tea, make some oatmeal and bring it all to my desk where I camp out for 8+ hours.

I enter the digital world. I respond to email after email; I blast things out on Mailchimp; I interact with early-stage startup founders and corporate employees that pay my company enough to cut me a paycheck. Usually, I eat my homemade lunch at my desk. (read more…)

Ask. You Won’t Sound Stupid.

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When I was twenty-two, I left New York for San Francisco, determined to move past a failed relationship and a failed presidential campaign. I had done all I could for both–all I was able to do at that time–and was ready for my adult life to truly start.

That adult life began with a healthy amount of mooching off family members. I stayed at my brother’s Berkeley dorm, a co-op, while he was out of town for spring break, sleeping in his bed and reading his roommate’s Harry Potter books. I felt like an interloper even though I had permission to be there, so I tried to stay under the radar, eating meals at the taqueria up the street and sneaking to the communal kitchen only for cereal. The cereal and milk were dispensed from large canisters that seemed impossible to empty. Nevertheless, I found a nasty note on the windshield of my car, which I’d parked in one of the many vacant spots in the co-op lot. The author of the note assumed I was a homeless person, and told me that I’d been seen stealing food from the kitchen and that I was trespassing. It was the result of a miscommunication that was quickly cleared up upon my brother’s return, but I felt attacked and too timid to plead my case, so I decided to move on. (read more…)

“I Wanted to See My Name on a Label” What Happens When a Passion Sours?

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“Follow your passion” is advice commonly dispensed, a trope of commencement speeches and career coaches. But what does it actually look like when someone follows a childhood dream through to a business? I sat down with Sheila Moon, the women behind her eponymous company, which specializes in women’s bike gear, to ask her about her experience doing exactly that.

Sheila always had a clear vision: she wanted to see her name on clothing labels. She worked hard over almost fifteen years to make it happen, launching the Sheila Moon brand in 2003. Yet, recently, what was a driving passion and a successful business became overwhelming and stressful, and her passion for design seeped away. Sheila described, “This was a dream I’d had and now it’s like a really nasty divorce where everything I loved, I now hate.” (read more…)

Trial by Ice: Two Years Alone in a Cabin in Maine

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I am not sure I know why I went to live all alone in a small cabin in the Maine woods in 1972, when I was 22 or 23. Maybe it was some sort of a delayed rite of passage.

I recall that I felt like I did not have much practical knowledge after growing up in a household in Nyack, NY where my businessman father introduced me to sports like baseball, sailing and skiing. But since he was neither an athlete, and had never sailed or skied before trying to teach me, these father-son outings were more often embarrassing than empowering during my high school years. I had four years of headiness at college and a stint teaching at a private boarding school in the mountains of northern California, but still no hands on experience, before deciding to move back East with a yellow Labrador, Jesse, in tow. (read more…)