Jerry Garcia Life Lesson #4

It is fashionable today to “fail harder” and to “fail faster.” These concepts from the worlds of communications and technology are meant to take the sting out of failure — the purpose being to encourage the kind of risk taking that accelerates growth and positive change.

Jerry Garcia Life Lesson #4: Take Risks

Playing it safe wasn’t Jerry’s way. He was an explorer, and by definition explorers take calculated risks. Sadly, when explorers lose their way, they can also lose their ability to calculate. Such was Jerry’s burden when it came to hard drugs, heroin in particular.

But it is not heroin, it’s LSD that is so closely tied to Grateful Dead and its musical risk-taking. The band and its songs were a jumping off place for the musicians and for the fans. LSD too is a jumping off place, and when you mix the two — Grateful Dead and LSD — you’re in for an epic journey. The band’s hyper-extended song, “Dark Star,” is certainly an epic journey. Performed live in concert “Dark Star” often clocked in at 30 minutes or more. What kind of band plays a song for more than 30 minutes? A band that wants to explore the kind of big ideas that need nearly infinite space to develop.

A band that plays a song this intricate and this long has immense trust in its own ability to pull it off, and in the audience’s willingness to stay interested and involved. LSD fueled the ideas that led to the creation of songs like “Dark Star” and “Birdsong” and LSD made listening to these acid-dipped songs all the more interesting. There’s no removing the LSD from the story or the historical record, nor should there be. Taking LSD was a risk that paid off in many positive ways for the band, for its generation and for new generations of people attracted to the music and to an authentic journey into the mind and self.

On another front, some of the risks we took to see Jerry perform may have seemed extreme to friends, coworkers and relatives at the time. In the summer of 1990, I mail ordered for the complete Europe Tour which was scheduled for October. I had never gone “all in” before. That is, I had never attended every show of an entire tour before, and here was my chance to do it and do it right. I asked for a month-long leave of absence from my job as Operations Coordinator at Conservatree Paper Co., a recycled paper merchant in downtown San Francisco. My boss said sure, but his boss said no way.

Big boss man’s name was Alan, and I recall vividly how Alan asked me what this trip to Europe was all about. I said I’m 25 and I’ve never been to Europe and now’s my chance. He asked why now? I said I’m going to see Grateful Dead in four European countries, is why now. He exclaimed, “People don’t do this!” I said I’m a person and I’m doing it. I added the only question was whether he wanted me back in four weeks. He did not.

Was it the right thing to do, quitting my job to see Jerry? That’s a rhetorical question. Of course it was the right thing to do. I knew there was a time-limit on the scene. That was made very clear to all in 1986 when Jerry slipped into a heroin-induced coma and nearly died. Trouble ahead, Jerry in red. But I digress. I knew, like we all knew, that there would be only one more chance to see Grateful Dead in small venues in Europe and that chance was going to take place during the month of October 1990. I also knew that a new job and new work would be waiting back home, so I didn’t mind taking the risk, not at all.

Europe tour 1990 was special in a lot of ways. For one, we all traveled by train so the experience was a collective one. In the U.S. after a show, you tended to go by car (or bus) to a nearby hotel or to a friend’s house. Lots and lots of little parties after and before the shows. In Europe, 3000 American Deadheads moved pretty much as one, by train, from city to city. This kind of travel made it easy to meet new people and make new friends. It was an epic adventure full of calculated risks, and I am better for having had it.

Previously: Jerry Garcia Life Lesson #3: Defy Convention