On April 12, 1963, Dylan marked a major turning point in his life during the most prestigious show of his career to date. It occurred at Town Hall in Midtown Manhattan.

Dylan’s fans had embraced him as the continuation of the beloved songwriter and singer Woody Guthrie, America’s mid-twentieth-century Dust Bowl poet laureate, who had penned “This Land Is Your Land” and many other classic Americana tunes.

That evening Dylan unexpectedly announced he was about to read something that he had recently written. Someone had asked him to contribute to a book about Guthrie, he explained, and the assignment was, “What does Woody Guthrie mean to you in twenty-five words?” Pausing at the utter absurdity of the mindless question, Dylan noted he “couldn’t do it. I wrote out five pages, and I have it here, have it here by accident, actually.” If all of that wasn’t enough of a jolt, he announced that the poem was called “Last Thoughts on Woody Guthrie.” By coining that title, Dylan left nothing to chance for his audience. He wanted to hammer home the point that he was his own man and people had better accept him. The poem deals with one of the themes—the inequity between the haves and the have-nots in society—that Dylan frequently wrote and sang about in that period. In an example of the free-form series of rhymes of the poem, Dylan read, “And your minutes of sun turn to hours of storm . . . I never knew it would be this way, why didn’t they tell me, the day I was born.”

The poem itself mentions Guthrie’s name for the first time in the final stanza, but Dylan’s fellow musicians could easily grasp the significance of “Last Thoughts on Woody Guthrie.” Eric Clapton told interviewer Roger Gibbons for the Telegraph, a publication devoted to all things Dylan, in 1987: “That to me is the sum of his life’s work so far, whatever happens.” Clapton elaborated on Dylan: “Basically, he’s a poet. He does not trust his voice. He does not trust guitar-playing.”

Dylan accomplished something that all successful people do, at one point or another: They decide that they are ready to step out of the long shadow of their mentors. In Dylan’s case, it must have been an emotional decision, for Guthrie loomed large to him. In No Direction Home, the 2006 Martin Scorsese–helmed documentary, Dylan said he had traveled to the East Coast in 1961 expressly to visit Guthrie in a hospital in Morristown, New Jersey. Later that year, Dylan wrote and recorded for his first album the evocative tune “Song to Woody.” In the late 1980s, in an interview in England, Dylan noted that in his youth in Minneapolis and Greenwich Village, he had been a “Woody Guthrie jukebox.” But the time had arrived at Town Hall for Dylan to be his own man. It was a sign of his personal growth. He was bursting at the seams with self-confidence and burning with ambition to take his art in a new direction.

It underscored a deep-seated need for him to take command of his public persona and point to a new direction. He was telling people that he would never discredit the influence of Guthrie on his muse and his life. But he was now twenty-two years old, the age at which his peers were graduating from their college campuses and entering the real world. Dylan, too, was advancing in his quest to make it big as a singer and songwriter. He had matriculated at the University of Woody Guthrie and was now progressing to a new world as well. Even though he remained intensely loyal to Guthrie’s legacy, Dylan recognized that he could no longer let music people and the society at large believe that he was primarily still an acolyte of Guthrie.

Dylan had gradually grown beyond the image of himself as the embodiment of Guthrie. He needed to tell the public that it had to adjust its perception of him. Dylan parted with the past in a respectful and smart manner. But his message was clear: Respectfully, folks, he all but explicitly told the throng at Town Hall, I am not the new Woody Guthrie any longer.

Think for Yourself

Dylan turned the biggest corner of his career when he started to write songs around 1961. Previously, he had exclusively sung the work of other songwriters, principally Guthrie. By coming up with his own tunes, Dylan was able to cut his ties with Guthrie and clearly establish his own voice.

This move enabled Dylan to put his stamp on the times and carve his own niche. The singer-songwriter is all too common nowadays, but in the early 1960s, the idea that a folksinger would write his or her own material was a fairly radical one because it was frowned on to thumb your nose at the musical standards. “Why would someone want to do that?” Ray Benson of the folkie singing group Asleep at the Wheel asked rhetorically on a 2007 disc tracing Dylan’s long career. “There’s so much good stuff out there already!” That was the sentiment when Dylan was trying to break into the folk music scene.

But Dylan knew better than anyone else that he had gone as far as he could by singing other songwriters’ classics. He was ready to put his imprint on the folk world. Talk about a supremely empowering personal moment of liberation. It was as if the young and precocious Bob Dylan had declared to the rest of the folk music world, “I am ready to make my mark, and I want the others to start following me from now on.”

By making the move to writing his own songs, Dylan was doing just that. For him, it was a moment to remember. As he wrote in Chronicles: “I can’t say when it occurred to me to write my own songs. . . . I guess it happens by degrees. Sometimes you just want to do things your way, want to see for yourself what lies behind the misty curtain.”

To truly become great, you have to step out of other people’s vision and into your own. For Dylan, this meant writing his own songs, and the decision was a moment to cherish.

It boils down to how much you’ll push yourself in the face of existing societal conventions. Have you ever done (or dared to do) anything comparable in your field to what Dylan pulled off? How do you go about pushing aside the expectations that weigh you down?

Sure, many people can tell you that you’re on top of the world and that they admire and even envy you. That sort of praise can become intoxicating. But when you believe your own press clippings, you’re on a fast track to self-destruction because you’ll lose sight of what you know is important: blazing your path and thinking for yourself, instead of living up to the image that the outside world has constructed for you.

You need a strong backbone to tell your most fervent admirers that you are turning your back on their notions. Some will understand, some won’t, and some will fight you every step of the way.

Yes, people are going to be surprised and, in many cases, archly critical of you. They’d rather keep you in the same place because if you grow and change, they’ll have to shift their way of thinking about you. And as we know, most people do not welcome change in their lives because it can be stressful. And so what? Who cares if the people give you flak? You can’t live your life simply to please the crowd. It’s better to try to be a leader than a follower.

We hate to admit it, but we do contemplate prospective disappointments and rejections. These fine points certainly matter to us—and to our detriment. We all fret about looking foolish or getting criticized if we dare to do something unconventional or unpopular. It’s human nature. But it also smacks of a frailty that can keep us from advancing and meeting our objectives. Fear makes us less certain of our ability to take on new responsibilities. Worrying about failing can be the biggest single factor preventing us from putting our best foot forward and charging into the fray.

Dylan has faced this crucible on more than one occasion, and any number of them would neatly provide a worthwhile example. But the case that shines through most prominently for me is when Dylan decided to expand his folk music repertoire and go beyond the kinds of protest songs that had made him a global phenomenon. Not many of us would have the guts—and there is really no other suitable word—to do what Dylan did in 1964, when he stopped composing finger-pointing songs, as he liked to call this style of songwriting, in which he made commentaries on the world around him and issued proclamations about injustice, race relations, politics, and tyrants. Instead, he would now write about what he was thinking and explore his own thoughts more deeply. He showed courage in openly going against the tide and doing what he wanted to do.

Dylan has made it clear that he had no interest in living out somebody else’s vision of his way of life. “Whatever the counter culture was, I’d seen enough of it,” he wrote tellingly in Chronicle. “I was sick of the way my lyrics had been extrapolated, their meanings subverted into polemics and that I had been anointed the Big Bubba of Rebellion, High Priest of Protest, the Czar of Dissent, the Duke of Disobedience, Leader of the Freeloaders, Kaiser of Apostasy, Archbishop of Anarchy, the Big Cheese.”

Dylan set out to challenge himself and go beyond the brilliant bluntness of “The Times They Are a-Changin’” and songs of that ilk. He would now push himself to reinvent the language of the folk song. But as we can see, anyone who has the musical genius to come up with the likes of “Mr. Tambourine Man,” “It’s Alright Ma,” “Gates of Eden,” and “Desolation Row” has clearly met the challenge. But the point is that Dylan would never have created those masterpieces if he’d stayed constrained in the public’s box. If he hadn’t had the wherewithal to break out of the quicksand, he wouldn’t have had the spark to invent new gems to supplement the older ones. You can appreciate Dylan’s stunning body of work on one level, and that is fine. But if you truly want to understand his genius, you must recognize that it comes along with his lifelong quest to stay ahead of the baying pack and to think for himself. He will please himself, no matter what, even if it means throwing a curve ball now and then at the same people who have always loved his work. He just will not live on their terms.

Do you have the strength to shed the expectations of others? It isn’t easy. Do you continually push yourself to change people’s perceptions? Or are you content to show the same face, the same persona, the same output that you always have? If you admire Bob Dylan, you’ll see that he has always been driven to be ambitious. That should be your mantra, too.

The China Syndrome

As you become more successful, you become a target. People begin to have expectations for you, and they expect nothing less than for you to live up to whatever they have in mind. When you don’t, they can react in a fury because you have failed to live up to their ideal of you. You cannot, however, let them make you into a false symbol, regardless of the consequences of your actions and decisions. It’s more important for you to remain true to yourself than to bend for someone else’s whims. Once you’ve lost your principles, you’ve surrendered your integrity to the interests of the mob. And when that happens, then they do indeed own you, and you’ve lost everything.

Take, for instance, the occasion in early April 2011 when Dylan performed in China for the first time in his career. He withstood plenty of criticism because he wouldn’t live up to everyone’s ideal of him and didn’t let other people push him around. In this episode, he illustrated the challenges you face when everyone wants a piece of you. When the word quickly spread that Dylan would play concerts in Beijing and Shanghai, people expected him to sing “The Times They Are a-Changin’” or another of his early social-protest gems to show his support for activists such as then-jailed artist Ai Weiwei, an outspoken critic of China’s policies regarding democracy and human rights.

These are laudable causes, for sure, but Dylan, as always, resists being a pawn in other people’s agenda. Since the early 1960s, advocates have demanded that Dylan be their leader. They expected him to be their spokesman, whether they were protesting the Vietnam War, nuclear power, apartheid, President Richard Nixon, or the wars in other places (El Salvador, Bosnia). Now as then, Dylan asserted his independence. He didn’t sing “Blowin’ in the Wind” or “The Times They Are a-Changin’” during his Beijing and Shanghai concerts and so braced himself for the backlash.

If you are going to assert your independence, you must inoculate yourself against critics. You must be prepared for people to second-guess your decisions and criticize you if you don’t do as they think you should.

No less than Maureen Dowd in the New York Times blasted him in her April 10, 2011, column titled “Blowin’ in the Idiot Wind,” neatly combining two Dylan titles, “Blowin’ in the Wind” and “Idiot Wind.” Dowd began her commentary by saying, “Bob Dylan may have done the impossible; broken creative new ground in selling out.”

Dowd personified the kinds of critics that he faced throughout his career. They failed to understand that Dylan was never going to be a poster boy for someone else’s agenda.

Going Your Own Way

I wouldn’t blame you if you rolled your eyes and said, “But Bob Dylan is a major star, so of course he can get away with making up or bending or ignoring the same rules I have to follow every day because I have a boss breathing down my neck twenty-four hours a day.” What, then, if Dylan worked in an office, the kind where we toil away day after day in relative anonymity? Could he get away with the same sort of behavior and expect to ascend to the top of the organization chart? Sure, he could.

He showed the virtues of betting on himself on numerous occasions. True, Dylan is the ultimate example of someone who is gloriously self-employed, but don’t let that fool you. Even Dylan has to answer to people in his life, such as the bean counters who run his record company, the concert promoters who book him in their halls, and especially you and me. Yes, we fans determine whether there will continue to be a market for Dylan’s recordings and performances. He has to please us. But he does it, over and over, by showing us that he won’t follow leaders—and he gives us hope because we can ignore leaders as well. Dylan, without even trying to, sets a worthy example for us to follow. And we, too, can do the same in our lives.

What it all comes down to is having an unshakable faith in your ability to fend for yourself and a willingness to take charge of the decision-making process. In earlier chapters I talked about the necessity of finding your destiny, but this is something different.

The course of anyone’s life can turn on a single decision because it can spark a series of changes. Taking charge is as much a state of mind as anything else. Once we have drilled into our heads the notion that we will be the master of our destiny, we are on our way to the thrilling feeling of self-discovery.

Nobody has to go rafting on a death-defying, grade-five river in Ecuador simply to prove his or her mettle. You can transform your life just fine by recognizing that you must make a change for any number of reasons, such as shaking out the cobwebs. Usually, however, we need to prove to ourselves—as well as to the other people in our sphere—that each of us is, indeed, our own boss.