Leadership, the Long Strange Trip

I just finished watching “What a Long Strange Trip It’s Been,” the newish documentary about The Grateful Dead, and I was stunned by what I learned about the life and untimely death of Jerry Garcia.

There are lessons here about leadership, success, and facing one’s shadow that can rock your world (pun intended) if you know how to look.

This article is going to focus on the weaknesses of Garcia, but this is not to discount his genius. Strengths and weaknesses are always two sides of the same coin. Garcia remains one of the greatest guitarists and songwriters in human history, and he pioneered the genre of improvisational rock that continues to flourish today.

He was also a deeply troubled, conflicted man who died precisely because he did not resolve the very issues that made him successful. He was a leader who refused to fully embrace the role, and this is exactly what I see every day in the CEOs and managers I work with. It’s also something I work on in myself, which is why this film was so sobering and touching for me.

While the film doesn’t say it directly, it’s easy to see that Garcia had issues related to freedom and authority. These were at the root of not only his own challenges, but whatever difficulties the band experienced. I’ll cite several examples to illustrate this.

Hell’s Angels

In episode four, John Barlow (one of the Dead’s lyricists) recounts how Garcia was criticized by members of their tribe for letting the Hell’s Angels into their inner circle.

“We had Hell’s Angels hanging around for ages…and those are people who don’t even try to be good guys… At one point, I complained to Garcia about what I thought was the unnecessary presence of all the Angels, thugging it up backstage, making people kind of nervous, and making it even harder for women in a scene that was already misogynistic to the max. And he said, ‘Well, you know, I don’t think that good means very much without evil.’ Which is true, but that doesn’t mean you need to always have a seat for evil at the table.”

In 1969, The Grateful Dead joined several other bands and 300,000 concert-goers for the Altamont Speedway Festival. The Hell’s Angels were hired, ostensibly as security, in exchange for free beer. (What could go wrong?)

In addition to violence involving several hundred people throughout the event, one Hell’s Angel stabbed a man five times, killing him, after he brandished a revolver about twenty feet from the stage.

No One to Blame

Here’s what Garcia had to say about it:

Garcia: Altamont was a microcosm of the world, which is us all, man…and the only way it’s gonna be dealt with is by each of us individually realizing what part they took in the murder….”

Howard Smith: Somehow I feel you’re maybe being too forgiving.

Garcia: I’m not forg—I mean, you know, what’s to forgive? There isn’t any blame.

Smith: There’s no blame?

Garcia: No, man. You can’t operate with blame, because who’re you gonna blame? We’re all on this planet. And all of our problems are all of ours. Not some are mine and some are theirs… You have to blame everybody… Hell’s Angels have happened because of freedom… they’re a manifestation of what freedom is, in essence, and so at some point or another, somebody has to say, “There can be no Hell’s Angels,” and who’s gonna say that?

No Boundaries

In other words, he’s saying, “Freedom means the absence of boundaries, and I’m not going to be the one to set them, because then I’m not free, nor is anyone else.”

Contrast this to what Mick Jagger, who also shared the stage, said about how he felt about the incident: “Well, awful. I mean, just awful. You feel a responsibility. How could it all have been so silly and wrong?” Jagger was punched by a concert-goer only seconds after exiting his band’s helicopter.

Garcia was the quintessential hippie, of course—a leader in the revolt against boundaries that typified the counterculture. The Dead, after all, was born in the infamous “acid tests” in the mid-60s, where the very boundaries between musicians and audience were dissolved, the moment of conception for the jam band genre we have today.

Misguided Worldview

The limit of Garcia’s worldview is on display here. He subscribed to a oneness paradigm imported from the east and aided by the hallucinogens of the day. He saw boundaries, including that of personal responsibility, as artificial and impedimentary. Boundaries, authority, and structure offended his sense of freedom. This aversion would eventually be his downfall.

John Barlow: There was a strong belief, primarily on Garcia’s part, that it was important that [the band] be leaderless. He did not want to be the leader. Nevermind that he was, and there was no way around it… and often times bad things happened because he wasn’t willing to assert what was pretty obvious… Nobody wanted to be in charge, and no one wanted to say “no” to anything.

A Leaderless Organization

By the mid-70s, the band had grown into an unsustainable organization. They had sunk a fortune into the brilliant-but-impractical “Wall of Sound” comprised of over 600 speakers, and they employed a large road crew to handle all the equipment. The band was supporting not only their overpaid crew, but their families as well.

In late 1974, everyone was feeling the strain, money was low, and still no one was leading.

“It was decided somehow that we were going to take a break,” said bassist Phil Lesh. “I did not want to take a break. I was having the time of my life!”

Rhythm guitarist and vocalist Bob Weir, on the other hand, was exhausted. “It’s not just the momentary fatigue that you’re running down. You look back on your lifestyle and you can pretty clearly see what it’s been doing to you. Then, prudence decrees that you’re going to have to alter your lifestyle, or you’re not going to make it very far. I don’t think that I can really fairly expect to live for a long time if I’m on the road six months out of the year.”

Weir had no idea how prescient he was when he said this in 1974.

Drug Use

While The Dead took a break, Garcia immediately launched The Jerry Garcia Band and continued to play as much as he could. It was clear to many that Garcia needed to perform in a way that was detrimental to his health. When the band got back together in 1976, Garcia had begun to use heroin.

Steve Parish was the de facto crew leader for over thirty years, but of course, there was no hierarchy anywhere in the organization. He said, “Jerry was…the heart and soul of The Grateful Dead. He was responsible for being the guy to keep this whole machination that we had built going. And, it’s hard to live up to that. The drugs that go along with being that person are not conducive to health and life.”

So there are drugs that go along with leadership? Hmm.

Avoidance of Power

The pressure of leadership was exacerbated by the fact the Garcia was literally idolized by the masses. He could no longer go out in public, unlike his bandmates, and the power he had weighed on him heavily.

In the 80s, when dangerously unmanageable crowds numbered in the tens of thousands outside the shows, Garcia refused to issue any statement asking people not to come without a ticket.

The band says they staged interventions here and there, and Garcia attempted to get clean a number of times. But what power did they have to hold accountable the leader of the band, who garnered even more control by refusing the role?

The truth is, as a leader, he was responsible not only for hurting himself, but for hurting the band and the worldwide community that followed them.

No Consequences?

There’s one consequence the band never used, despite the fact that Garcia was literally dying on stage, one show at a time. Playing music was as much a drug for him as heroin was, and he needed a break from them both.

In July of 1986, after three straight shows in the summer heat, he slipped into a diabetic coma for five days. He lost some motor function and had to relearn how to play his instrument.

This might have been a good time to draw the line—for Dead members and every other professional in music to come together and say to Garcia, “Your health is more important than using heroin and making music, and none of us will play with you, crew for you, or promote you until you get clean.”

It’s understandable why this never happened. On the outside, Garcia was a freedom-loving, teddy-bear of a hippie. On the inside, he was a control freak who refused to look at his distorted values about freedom, his extreme discomfort with his own power, and his responsibility to lead.

Imagine being a leader of a multi-million-dollar organization, with millions of idolizing fans, when your worldview says the power and authority you have is wrong.

Mickey Hart (drums) was matter-of-fact: “Jerry Garcia was a lot of great things. He was a really cool guy, you know, until he killed himself… that’s really what happened.”

In 1995, at age 53, Jerry Garcia died of a heart attack in a rehab center. One part of him had tried to get clean again. But another part of him probably thought suicide was an act of integrity.


“If we had any nerve at all, if we had any real balls as a society, or whatever you need, real character, we would make an effort to really address the wrong in this society, righteously.”

– J. Garcia


When he died, Garcia had a net worth of $40 million and the hearts and minds of at least as many people. We’re left to wonder what might have happened if his loved ones had drawn the line and he had faced his arch nemesis: the healthy boundary.

Surely he, like all of us, did the best he could. Thank you, Jerry, for everything.


Leadership is never easy. It takes a great deal of courage to look at how your issues affect everyone else around you—and to change. If you struggle with fully embodying your role as a leader and mentor, I invite you to check out the Clear and Open Dojo. In addition to the larger professional group, I host leaders-only group coaching sessions, where CEOs and managers share and receive feedback on the unique challenges they are facing.

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