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

Jerry Garcia Life Lesson #1

Jerry Garcia was born on this day in 1942. In the years since his death on August 9, 1995, Garcia fans have taken to celebrating “Nine Days of Jerry,’ which covers the span from August 1st (his birthday) to August 9th.

This year, with encouragement from Darby, I am going to share key insights, a.k.a. lessons learned from Jerry — one a day for nine days.

Jerry Garcia Life Lesson #1: Stretch

Stretching is both a physical act and a metaphorical framework.

Top performers stretch to achieve a desired state of limberness, which in turn allows them to reach much further and higher than they otherwise could. Before going on stage, Jerry used to run through scales to prepare himself physically for the challenges of playing a three-to-five hour show. But it was during his shows where his yogic mastery was truly revealed — few artists have stretched their form to its breaking point and survived the journey.

Long before Jerry became the iconic Captain Trips (and unwilling spokesperson for the Haight-Ashbury scene), he worked hard to learn the rigors of folk music. He played acoustic guitar and banjo and got his voice in strong singing shape. Add LSD and an explosion of consciousness (and societal turbulence) to the mix, plug it in and turn it up and you have the beginnings of Grateful Dead.

Let’s use “Viola Lee Blues” to illustrate the point. The song was written in 1928 by Noah Lewis, an American jug band and country blues musician. “Some got six months, some got one solid year.” Viola Lee Blues is a traditional ditty about a man lamenting his prison sentence. In the hands of Grateful Dead, the song gets opened up considerably, thanks to the weaving of jazz idioms into what is a very simple blues construction.

You might say Jerry and friends “stretched the shit” out of this tune. You’d be correct and it’s what made Jerry’s work and the band’s so compelling. When your mind is stretched far and wide it can hold a lot more information, and Jerry’s held a deep reservoir of American roots music, jazz, classical, and more, which he could tap in an instant for just the right effect.

In my own life, I make sure to stretch out daily as a writer. Like Jerry, I am attracted to and capable of working in a variety of forms (journalism, advertising and literature). And like Jerry I have my main gig as a ad writer and several nourishing side-projects. The rewards of cross-pollination are found here. For example, if I write a particularly poetic line for an print advertisement, it makes the ad better and it loads commercial communications with an artfulness it desperately needs.

There’s also a degree of patience woven into the act of stretching, which I like. Stretching is what we do to prepare and that’s the key. We’re too often in a mad rush to succeed or do this or that, but the reality is we must first stretch, breathe and gather ourselves before taking the stage.