As Bob Dylan discovered at various points during his career, success can be quite complex. There is no manual for handling it correctly; it comes strictly from on-the-job training and an unscientific process of trial and error. It can seem like a vicious circle, too. When our accomplishments beget expectations, ours as well as those of other people, we can begin to feel tension and lose focus. Expectations, in turn, cause stress. This stress ultimately produces anxiety—and before we know it, we’re cursing our hard-earned satisfaction instead of enjoying it. And it doesn’t matter, either, how cool our friends and colleagues continue to tell us that we are. In fact, the more accomplished they gush we have become, the more we need to live up to. Ultimately, these pressures become oppressive.

Right before our eyes, everything changes. What had once seemed like some kind of an impossible dream—achieving a measure of affluence and recognition—can, instead, feel overwhelming. It’s even more profound when someone attains a large scale of fame and fortune on top of it all. Eventually, this morphs into an unwelcome burden. And then what becomes of us? What can we do when “be careful what you wish for” goes from being a cautionary tale to our actual way of life? How well we handle a sudden rush of success can define us. There is, alas, no pamphlet for handling the strain that comes from a rush of wealth and fame. We imagine that successful people are sitting on top of the world when, in fact, they’re struggling mightily to live up to expectations.

Whither Dylan? Just as he has shrewdly constructed a strategy for attaining success—by learning how to play folk music for a time in the outpost of the Twin Cities, before graduating to the mecca of Greenwich Village and taking the town by storm—he has also demonstrated how to survive the effects of it. Whether you want to chalk Dylan’s durability up to his intelligence, self-discipline, or good fortune, it helped him dodge becoming a rock ’n’ roll casualty, who choked on the excesses and numerous temptations, like Jimi Hendrix, Janis Joplin, Jim Morrison, Amy Winehouse, and Whitney Houston. On many occasions, Dylan has experienced the kind of massive strain that idolatry—on an out-of-control, almost unimaginable scale—can produce. “When he is recognized, it’s every five steps,” drummer David Kemper said (in a 2007 audio documentary about Dylan’s life and career) of the crowd that invariably follows him around from town to town.

He has withstood the cauldron of public adulation by finding inventive ways of dealing with the tumult that is constantly swirling around him. More often than not, he has done what comes naturally: fall back on his love of writing and playing music, and use it to help him keep a sense of proportion. Dylan felt the bittersweet tug of success primarily at three points in his long career: first, when he became the king of folk music in the early 1960s; second, a few years later, when he crossed over to the rock ’n’ roll scene and enjoyed massive praise for “Like a Rolling Stone”; and finally, in the 1980s, when he needed to mount a comeback and prove his relevance. Thanks to his muse, Dylan could achieve the best of all worlds: professional satisfaction as well as personal fulfillment.

You Have to Please Yourself

Bob Dylan could teach us plenty about coping with the pressures of stardom, especially the overnight variety. He was barely out of his teens when he wrote his first major song, “Blowin’ in the Wind,” in the spring of 1962. It immediately became an anthem of the twentieth century, and beyond. Although we can’t expect to enjoy that brand of mammoth success, we can certainly take note of and appreciate exactly how Dylan has maintained his emotional and physical equilibrium in the face of tremendous pressures over a fifty-year cycle. Dylan has gone through, albeit on a massive scale, what a lot of us experience in our day-to-day lives and careers. How do you deal with the adjustment of being hailed as a star in your workplace or family or circle of friends? How do you act (or react) when it seems that everybody wants to bask in your glow and, more intrusively, wants something from you—whether it is love, advice, money, or attention? The same people who once needed only to joke around and hang out with you now require something from you. When everyone is telling you what they think you want to hear, it’s very hard to know who your real friends are. The stress of sudden stardom was taking a huge toll on Dylan’s central nervous system. “I’m going through bad times,” Dylan told friends at around that time, according to Anthony Scaduto’s biography Bob Dylan. “It’s blowin’ my head.”

His solution was at once novel and practical: He focused on pleasing himself and let the chips fall where they may with his fans, peers, and business associates. He showed a facility throughout his career for following his muse and not kowtowing to what the suits or the audience demanded of him. He demonstrated again and again the value of keeping your own conscious, if only to allow yourself to take charge of your destiny. Even though Dylan is one of the most famous and accomplished people on the planet, his particular burdens are not so different, in theory, than yours or mine. Dylan has an occupation that places unique demands on him—so do you. Dylan has to keep the customer satisfied, as Paul Simon once put it—and you do as well. Dylan has to strike a balance between his public and private lives—and don’t you identify with that predicament? It all comes down to how well you can cope with your own success.

Have you felt that way, when your success is squeezing you and making you feel isolated? Perhaps you, too, have felt like a prisoner of it. Success can be debilitating for all sorts of reasons. Once you’ve proven you can excel at doing one task, the odds are good that your bosses will continue to press you to keep on doing it, making it difficult to break out of your pattern and take on new assignments. Have your superiors ever pigeonholed you and made it tough for you to break out of their image of you? When this occurs, it becomes very difficult to grow. If you’ve felt the brunt of this treatment, you’ve probably failed to get hired or transferred or promoted because people want to keep you where you are. It’s discouraging, to say the least.

Another by-product is imagining how the people in your life now regard you. Even if you struggle to remain the same, they look at you differently, perhaps suspiciously, because you have exceeded their own expectations. It can be extremely hard to change your image when people are content for you to stay in your box and continue performing the exact same functions in the exact same ways. The sad fact is that we live in a bureaucracy, and people don’t usually have much imagination or sense of adventure, and you can get caught in the mill. But you can’t let other people measure your value. You can’t wait for the powers that be or the public to give you the opportunity to change and grow when they can’t see anything that isn’t right in front of their faces. It’s up to you to seize the moment and show people what you can do. Not many of us are willing to do this. We feel paralyzed by fear and are reluctant to risk disappointing the people we depend on for approval and a good life. This is a shame, but the solution is quite simple: If you believe you have what it takes to excel, just go for it.

Dylan showed us how to defeat this syndrome. Just observe what he went through. He was determined to shake the public’s expectations for him after he had established himself as the darling of the counterculture in the early 1960s. He recognized that he needed to do something bold and unexpected on the next album in 1964. Pointedly, it was titled Another Side of Bob Dylan. Despite the giveaway title, the audience hoped and expected, once again, to hear his brand of protest music, such as “The Times They Are a-Changin’,” “Blowin’ in the Wind,” and “Masters of War.” He instead teased his listeners by opening his fourth album with the track “All I Really Want to Do.” Instead of what had become his characteristic, blunt, clipped vocal style, he actually laughed and even yodeled on the song, making it clear that his fans were, indeed, getting another side of Bob Dylan.

Dylan refused to subscribe to society’s image of him, and he took it on himself to change his reputation. As he often does, Dylan was making a larger point that went beyond the grooves of a record album: Fight like hell to avoid having to live up to someone else’s image of your self-worth. No matter how successful you have become, you can alleviate the pressure by not taking yourself oh-so-seriously. Most crucial, when you are living inside of a pressure cooker, take a step back and think about what you can do to keep a sense of balance.

Take One Giant Step Back

Sometimes, the best solution is to stop—and step off the merry-go-round for a time. Dylan bravely walked away from the limelight at the peak of his popularity. By the start of 1967, Dylan badly needed to have a break from the madness that had engulfed him for the previous several years. Dylan discussed the burst of chaos with Scaduto in a 1971 interview: “The pressures were unbelievable. They were just something you can’t imagine unless you go through them yourself. Man, they hurt so much.”

Chances are you can relate to an experience in which when the people you’ve trusted seem intent on piling on the pressures till you feel as if you were going to reach your breaking point. With Dylan, as we look back, the responsibilities do seem formidable on many levels. Still only twenty-five years old at the dawn of 1967, he was then recovering from a broken neck he had suffered in a motorcycle wreck the previous summer. Before the accident, he had just completed a grueling work schedule. From 1964 to 1966, he had recorded four studio albums, including Blonde on Blonde, rock ’n’ roll’s first two-record set. Somehow, each of his new recordings topped his previous effort in terms of creativity, originality, and a sense of ambition—a special accomplishment, and a rather stressful one at that. He had also toured the world, proud to show off his new sound, only to be greeted by a chorus of boos from disillusioned fans everywhere. They loudly expressed their resentment for his decision to abandon folk music and go electric. He had also churned out a television special and his first book. In addition, Dylan had gotten married and had fathered his first child. With concerns about his health, career, and personal life, he encountered major challenges on all sides.

Understand, it was unimaginable that a pop star on Dylan’s lofty level would retreat into seclusion. Dylan all but retired from the stage and had his management company cancel the sixty-five U.S. concerts that had been set up for the autumn of 1966, beginning with the cavernous Yale Bowl in New Haven. Dylan answered the demands on him by setting a new agenda. Put simply, Dylan took charge of his life. He informed Columbia Records that he wouldn’t be doing yet another new album, and it was free to release Bob Dylan’s Greatest Hits. He didn’t go back into the studio to make a new album until the autumn of 1967. He quit touring, a profoundly rebellious decision in a business in which practitioners had always thought they had to be seen by the public as a way to continue selling their records and satisfy their restless egos. He even stopped granting interviews. He relaxed up in Woodstock, away from the craziness. What he did in this simple stroke was nothing less than revolutionary. He was, as usual, far ahead of his peers. Consider that when John Lennon celebrated his life out of the spotlight, in a terrific song called “Watching the Wheels,” he did so thirteen years after Dylan stepped back.

This is one of the most difficult things any of us can do: take control of our lives and change our destinies. It seems so much easier to let someone else—a family member, a boss, a business manager, an agent, or a financial planner—make the tough decisions for us. Dylan had done that for years but decided, as he later said in a 1974 interview with Rolling Stone, that the “leeches” in his life had played a part in creating a vicious circle of stress for him.

Of course, we all don’t have the financial wherewithal to retire from public life, as Dylan did. But the key takeaway here is that Dylan knew when it was time to retreat from the limelight and stop competing for a bit, as he recharged his batteries. This requires an enormous act of will—especially when everyone else judges you to be at the peak of your powers.

The people in your life are often urging you to keep firing on all cylinders, possibly because they need to ride on your coattails. And the act of taking yourself out of the spotlight, by your own volition, is an extremely wrenching move. Most successful people are achievement junkies. They thrive on competition and the satisfaction of winning. Success is most definitely a fantastic high and much more fulfilling than any drug. Most of us simply aren’t strong enough to resist the siren song. It seems so much more natural to remain on the merry-go-round of life and continue doing what you have always done—even if you suspect, in your heart, that it is grinding you down, driving you crazy, or literally killing you.

Dylan also found refuge from the insanity in his family. We often read Mommie Dearest–type accounts, in which children feel their parents weren’t there for them throughout their lives. It’s especially acute when celebrities are involved because of the mammoth publicity they invariably receive from the gossipy media.

In Bob Dylan’s case, however, there was none of that. In fact, I was struck by the outpouring of affection that Jesse Dylan, Bob Dylan’s eldest son, had for his dad when I interviewed him for a MarketWatch piece that appeared on March 26, 2010. I had a feeling that Jesse and I would get around to talking about his father at some point, but I wanted to tread lightly because I knew from reading scores of books and speaking with people in Bob Dylan’s circle that he was an intensely private man. I assumed that Jesse would also guard the family’s privacy, and I wanted to respect his wishes. Still, I was curious to find out what I could.

My interview with Jesse Dylan occurred long before I ever had a contract to write this book. I had been intrigued by Jesse’s commendable public service in Lybba, a nonprofit that sought to use social media to help bring together doctors, researchers, and patients to help improve the understanding of medicine. Inevitably, our conversation swung around to Jesse’s influences and roots—and, sure enough, you-know-who popped into our conversation.

I suggested that Jesse was carrying on the good work in society that Bob Dylan had done so many years earlier with his galvanizing 1960s songs. As I wrote in my column, “While evidently flattered, Jesse said a comparison ‘is not apt. I’m a translator. I take what other people are doing.’”

The affection that Jesse feels for his father came shining through during our conversation, which took place in the East Village of Manhattan, a stone’s throw from where Jesse had attended New York University during the 1980s, and Bob Dylan had set the world on fire two decades earlier.

I had written in my column on Jesse Dylan: “One of Jesse’s comments stuck with me, though. When I mentioned that I’d admired Chronicles: Volume One, Bob Dylan’s acclaimed 2004 memoir, he nodded and said: ‘He is an even better father than writer. He is my best friend.’”

Finding Fun Again

Dylan has had his ups and downs over the years, and his public persona has often reflected whether he is happy or not. In the 1960s, he was often photographed with a smile on his face. But two decades later, he came across as a rather rigid, severe individual, possibly because a lot of people still retained their late-1970s image of him as a born-again Christian. It can be very tough to shake a powerful media-fed image like that one.

As the decade wore on, the indelible image of the public Dylan was his erratic and bizarre performance at the monumental Live Aid benefit concert on July 13, 1985, in Philadelphia. Dylan was admittedly hampered by a faulty sound system and sabotaged by Keith Richards and Ron Wood of the Rolling Stones, who had joined Dylan on stage but seemed to be on another planet as they played backup guitar. Dylan simply looked out of synch.

In photos taken at the time, Dylan looked like a guy who wasn’t having any fun. By his own admission in Chronicles, he was burned out, undermotivated, and disenchanted with the music industry. More likely, Dylan was just plain tired of pleasing people and had gone as far as he could go at that period. He needed to remember why he had decided to make music in the first place—for the fun of it and the sheer challenge of creating magic. You don’t have to be a musician or any kind of an entertainer to understand what Dylan was experiencing.

I, for one, can relate to this kind of syndrome. Can’t you? There are times when work feels like nothing more than drudgery. It’s a job, not an adventure, and the fun and thrill of discovery are nowhere to be found.

When this happens, sometimes you just have to stop taking yourself so seriously. It’s essential. You can’t eliminate the pressure of doing a good job and winning acceptance, but you can decide to start having fun again. For a lot of us, the happiest times of our lives occurred when we found ways to whistle while we worked. We could laugh through the aggravation and tension of everyday life.

Dylan’s answer was the Traveling Wilburys, an impromptu band of superstars put together in Los Angeles in the spring of 1988 by his good friend George Harrison. Harrison invited Jeff Lynne, formerly of the Electric Light Orchestra, Tom Petty, and Roy Orbison to join them, and the experience revitalized Dylan, primarily as a songwriter. He hadn’t much tried his hand at creating songs with funny lyrics in that decade, but he came alive on this experimental album. He wrote “Congratulations,” “Dirty World,” and “Tweeter and the Monkey Man,” the latter two tunes being rich, clever homages (or send-ups) of Prince and Bruce Springsteen, respectively. The album turned out to be a big hit with critics and the public, thanks largely to Dylan’s involvement. He benefited in turn, too, as it provided the spark for him to write the well-received songs on his next album, 1989’s Oh Mercy. By dialing down the intensity button and learning to have fun, Dylan also learned a lesson. Now he can teach it to us.

Once we have made the big time, our first impulse may just be to sit back and soak up all of the applause and act as if the adulation were going to go on forever. Guess again. Life doesn’t quite work that way. Once we’ve accomplished a goal, the pressure is on to maintain or exceed that sort of success again and again.

What Dylan shows us is that the key to handling success is not to let the pressure to excel swallow us up. The journey back to personal fulfillment can be the most rewarding part of our lives. How we go about recharging our batteries says a lot about us.