Freedom’s Songwriter

“Like a bird on a wire, like a drunk in a midnight choir, I have tried in my way to be free.”

—Leonard Cohen, “Bird on a Wire”

Twenty-six years ago, I was confronted with a career-defining choice: Accept an unsolicited offer to become the marketing director of a fledging video game company or attend Harvard Law School. Naturally, I chose Harvard. It turned out that the man who called me was Bobby Kotick, the CEO of Activision—today one of the largest and most successful video game companies in the world. The rest is history.

John Perry Barlow also received an offer to go to Harvard Law School but, unlike me, he turned it down. This paved the way for the adventure of his life, as described in his terrific new book “Mother American Night.” Growing up on a large ranch in Wyoming, Mr. Barlow was a real-life cowboy or, as he liked to put it, a “cattle baron,” since his family owned the ranch. As Wyoming is very small and he came from a prominent family, he became friends with just about every major politician in the state, from Sen. Alan Simpson to Vice President Dick Cheney. Mr. Barlow’s colorful background was such a stereotype that his pal Timothy Leary (the infamous evangelist of LSD) called him “John the American.” As a stereotypical Great Plains westerner, Mr. Barlow lionizes outlaws, quoting Bob Dylan who wrote “to live outside the law, you must be honest on a certain level.”

Where did Mr. Barlow’s uber sense of freedom come from? Mr. Barlow was a wild child, which got him shipped off to boarding school where he met another wild child, Bob Weir, co-founder of the Grateful Dead, for whom Mr. Barlow wrote dozens of songs from “Mexicali Blues” to “Hell in a Bucket.”

Mr. Barlow’s youthful nihilism took him to the edge of the abyss, including becoming an aborted suicide bomber and both a drug dealer and a user. Eventually, he evolved into a middle-aged tech evangelist, earning him a spot in the Internet Hall of Fame in 2013 and a fellowship at the same Harvard he once turned down. “Cyberspace is a perfect breeding ground for both outlaws and new ideas about liberty,” he contends. Some of his notions about “freedom” derive from his work with the Grateful Dead, who famously allowed fans to record their shows. This sense of “community”’ is what he is after.   

The appeal of the ranch life is mystical in American lore and its healing qualities appeal to some of the most unlikely sources. Jackie Kennedy Onassis sent her own wild child, John F. Kennedy, Jr., to live and work on Mr. Barlow’s ranch for a summer, resulting in a life-long friendship between the two. Mr. Barlow laments Mr. Kennedy’s tragic end, noting that he had all the chips lined up to be a “great man.” What he wanted instead was to simply be a “good man” and to escape his unwanted fame. It likely was his search for freedom that killed John F. Kennedy, Jr.

For all you Deadheads, this book may not be for you. Beyond Mr. Barlow’s songwriting prowess and his friendship with Bob Weir, his opinion of other band members and Deadheads in general is not very good. He recounts one fan telling him that the “Dead are more important to me than my family my religion and my school.” Mr. Barlow advised him to reexamine his priorities.  

As professionals, we all face forks in the road. Mr. Barlow took the road less traveled from darkness into light, and now into immortality with his dozens of songs for the Dead. There are many choices and opinions of Mr. Barlow that I do not admire, but his sense of freedom that enabled him to lead an extraordinary life (he died shortly before the publication of this book) made me think a lot about my own career and the advice of others.

A lot of the advice you hear these days at college graduations and elsewhere is about following your passion. It sounds great, but only those who are truly free with the willingness to fail, both financially and mentally, can do so.  Mr. Barlow rolled the dice on the freedom train, which could have ended him 100 times over as it did his good friend John F. Kennedy, Jr. Instead, he ended up with a measure of greatness.

Most people are unwilling or unable to take such a risk, and I certainly am not advocating for any of the extremely risky choices made by Mr. Barlow. But that does not mean you should not follow your passion. You should, or at least strive one day to get there. As Kris Kristofferson wrote, “freedom’s just another word for nothing left to lose,” and freedom is largely a state of mind. Happiness is helped by financial security and mental calm. But to get there requires freedom.