Bob Dylan Has a Message For You: You’d Better Start Swimmin’

UPDATED: May 13, 2024
PUBLISHED: August 16, 2012

What does Bob Dylan mean to you?

Do you think of him as the impossibly young-looking folk singer who in his early 20s wrote such civil rights and antiwar anthems as Blowin’ in the Wind, The Times They Are A-Changin’ and Masters of War? Or is he the frenetic rock ’n’ roll star behind the shades who got in your face and howled “How does it feel?” in his first hit single, Like a Rolling Stone?

Then again, perhaps your indelible image of Dylan rings truer to the man on the cover of his Nashville Skyline album, the country squire of Woodstock, N.Y., who crooned Lay Lady Lay. Maybe he sparks impressions of the 30-something wounded romantic who opened up his heart in 1975 in the brilliant confessional album Blood on the Tracks and then followed it up by telling an unforgettable saga of racial injustice in the hard-rocking song Hurricane.

Then again, the younger Dylan fans want to live in the moment, right now. They prefer to reflect on “their” Bob Dylan, by admiring the beauty and power of contemporary Dylan and appreciating the world-weary troubadour who opened the 21st century by singing: “I used to care, but things have changed.” He told the grim story of the post-9/11 reality in America in the classic tune Workingman’s Blues #2. And Dylan reminded us of another national problem in 2009 in the aptly titled song Life Is Hard, which focused on the huge percentage of young adults who graduate college and can’t find a job.

Any one of these representations, as well as a plethora of others, would fit and be completely reasonable. Everyone has his or her special image of Dylan, after all. What separates Dylan from so many others in his field is his stunning longevity.

And Dylan, who turned 71 on May 24, refuses to rest on his ample laurels. He continues to make profound musical statements and add to his legacy. And what a legacy! Remember, the man has remained a major presence in our lives for as long as most of us can remember— since the early 1960s, to be exact.

But it is a shortsighted mistake not to look beyond Dylan’s music when you want to understand his 50-year record of success. Naturally the music is an entry point. But think about it: What qualities have enabled this man to touch our lives again and again and again, in so many ways?

We can learn many valuable life lessons as we strive to realize the greatness in ourselves by studying Dylan’s life. We can look at the many occasions when he had to pick himself up off the canvas after getting knocked down by critics. Dylan can show us how we can reinvent ourselves, something he has done repeatedly to great results. He does things on his own terms. He has crafted a vision for his path from day one and has refused to veer from it, even though he might well have experienced lofty short-term gains. This man is the ultimate careerist—and I mean that as a compliment.

Granted, maybe you can’t learn how to write a song as majestic as Blowin’ in the Wind. But you can understand from studying Dylan’s example how to solve your problems and remain in control of your life and work.

Having just published a book on him, I have a special appreciation for Dylan’s less-publicized gifts: his intellect, work ethic, competitive nature, restlessness, quest for excellence and his desire to continue to evolve. He stands for a lot more than a batch of wonderful, iconic songs. I have scrutinized the ways in which Dylan has flourished, and I glimpse much more than a minstrel or a troubadour. He is never content merely to go along with fads and trends. He observes the scene of the nation, the music industry and the world around him, and he makes it his own. When you think about it, this is the secret sauce of achieving longevity, of remaining relevant in changing times and of being regarded by your fans as a leader in turbulent times.

Bob Dylan, a self-help guru?

Hear me out!

I first started to see Dylan in a new light when I read his own 2004 memoir, Chronicles: Volume One. I was impressed by his recollection of how he rebuilt his lagging career, which suffered in the 1980s as MTV and other factors put Dylan on the defensive and briefly made him seem out of touch with the rhythms of the music industry and the American psyche. Dylan solved his problem of being famous but not popular in the ’80s in a daring manner. He sought to reconnect with his fans and show them a side of the legend Bob Dylan that they hadn’t seen before. He toured incessantly and by doing so found a way to reach the children of the baby boomers.

Dylan, who was born Robert Allen Zimmerman on May 24, 1941, in Duluth, Minn., personifies a great American success story on many levels. A self-made man, he has led a wildly adventurous life. Columbia Records released his first album, the eponymous Bob Dylan, in 1962 (by the way, that was the year he wrote Blowin’ in the Wind, arguably the most famous anti-war song of the 20th century (and beyond). But the singer/songwriter is not one to bask in the glow of his long-ago triumphs. Dylan has annually played about 100 concerts all over the world since he launched what media wags like to call his “Never Ending Tour” in 1988. While Paul McCartney and The Rolling Stones—his two closest peers in the music world—seldom seem to record new material, Dylan still comes up with a new timeless classic every now and then, such as Workingman’s Blues #2, a gem from his 2006 album Modern Times, which topped the Billboard charts.

So how has Dylan done stayed on top? Here are 10 lessons, and the beauty is that you, too, can put these dictums into action:

1. Forget about today: Dylan looks ahead. He always has. He has made it his mission. It’s a philosophy that would serve anyone well.

2. Shun the naysayers: It’s a regrettable fact of life that people will try to keep you down. Business rivals will detract from your accomplishments. A boss may feel threatened by your ascent. Sometimes it really does seem like everyone’s a critic, right? But you cannot let the negative voices derail you from your quest. You must not let them beat you at your game. Dylan was blasted by those who resented his personal and musical explorations after embracing organized Christianity, beginning in 1979 when he went to Bible school in Southern California for three months and emerged with the songs for his terrific album Slow Train Coming. Dylan didn’t let the nattering nabobs discourage him. He gained strength through his newfound faith—and created some of his best music as well.

3. Create a personal revolution: When he was a teenager growing up in Minnesota’s bleak Iron Range area, Dylan began to have a vision for the rest of his life. All he intended to do was be a musician. He was lucky, in a way, to have found a vocation so early in his life. But it’s never too late for any of us to create a personal revolution of our own. Dylan listened obsessively to the radio stations that played everything from the Grand Ole Opry to blistering Chicago blues. He soaked it all in and learned his craft. By the time he hit Greenwich Village in January 1961, he was ready to fulfill his life’s ambition and make it in music.

4. Blaze your own path: Dylan has been a lifelong trailblazer who has contentedly followed his muse. Dylan’s most prominent example of this trait occurred in 1965, when he went from folk music to rock ’n’ roll and recorded his single Like a Rolling Stone. Dylan forever put his mark on the music industry by coming up with that six-minute song, by far the longest single ever attempted. By comparison, The Beatles had released Ticket to Ride, which clocked in at a bit over three minutes, then the group’s longest single. By smashing the boundary on what a recording could represent, Dylan opened the door and encouraged other musicians to be adventurous, too.

5. Always remain innovative: Dylan constantly seeks challenges. By early 1966, the former king of folk music had become the prince of pop. He had made all of his recordings in New York City up to that point. But he sensed it was time to break new ground and recorded most of his next album in Nashville, Tenn. He made a fortuitous decision. Blonde on Blonde proved to be one of his most successful and innovative works. Many people around him, including his hard-driving manager, Albert Grossman, tried to discourage Dylan from making such a radical shift. But Dylan knew best. He knew he had to continue to innovate—even when he was ruling the rock ’n’ roll roost.

6. Never rest on your laurels: In 1975, Dylan was restless. His album Blood on the Tracks had restored Dylan to a position of idolatry. The year before, he had toured North America with The Band, one of the most respected groups in all of rock ’n’ roll, and sold out Madison Square Garden, the Los Angeles Forum and other large arenas. In autumn 1975, Dylan reversed form by playing with a backup band that consisted mostly of unknowns and performed in small halls and on college campuses. It was the Rolling Thunder Revue, one of Dylan’s most-appreciated musical adventures.

7. Bet on yourself: In the early 1990s, Dylan was at a low point. Critics ripped his newest album, 1990’s Under the Red Sky, and sales weren’t too good, either. Dylan needed inspiration. He needed to take a break and get off the treadmill of recording a new album every year. He retreated to his garage studio and recorded Good As I Been to You and World Gone Wrong, two albums featuring only him singing and playing his trusty guitar and harmonica. He returned to the kinds of Americana-tinged folk songs that he had loved so much and sung as a student at the University of Minnesota. The result was therapeutic. Dylan gained strength and eventually roared back with the Grammy-winning album Time Out of Mind in 1997.

8. Take charge of your destiny: Be a leader, not a follower. We have heard this exhortation since we were little kids. But it’s not easy to take control of our lives. We have to make a very big bet—on ourselves! Are we up to the task? Bob Dylan certainly was, when he decided to take the radical step of dropping out of the University of Minnesota midway through his sophomore year to move to Greenwich Village to become a folk singer. It was a huge gamble. But Dylan knew he could be a success. If you’re confident in your abilities, nothing can stop you, either.

9. Stand apart from the crowd: It’s so tempting to join the crowd, isn’t it? It’s easier not to take an independent stand. Hogwash. By blending in, you diminish yourself and don’t allow your originality to pour forth. Dylan experienced this when he came to New York in 1961 and embarked on his path of folk music, even though he could have immediately made more money by writing pop songs. He stuck to his guns, and it sure paid off.

10. Learning from both elders and protégés: We’re never too young or old to learn from the people around us. Anyone can inspire us and provide a sense of direction when we need it the most. When Dylan was starting out as a folkie, he viewed Dust Bowl balladeer Woody This Land Is Your Land Guthrie as his role model. By the late 1980s, he needed someone new to push him. He found that person in U2 lead singer Bono, 19 years Dylan’s junior. Dylan had written a batch of new, personal songs, and Bono exhorted him to record them, pushing Dylan to work with the fiery music producer Daniel Lanois. The Dylan-Lanois collaboration yielded the 1989 album Oh Mercy, which many critics and Dylan fans regard as his best solo work of the decade.

11. Surprise! A bonus tip! Leave your comfort zone: Life can seem so easy, you know? We bask in the glow of what we have accomplished and feel good about ourselves. But what happens when a routine becomes stifling, and we desperately need something to jolt us out of our doldrums? The answer is doing something unexpected—radical, even—to lift us out of our comfort zones. This requires courage, above all else. Dylan encountered this condition in the early 1970s. He was having a tough time coming up with new songs and had reached a creative trough. To regain his spark, he did something startling: He acted in the Sam Peckinpah Western Pat Garrett and Billy the Kid (and did the soundtrack as well). The move worked brilliantly. Dylan wrote Knockin’ on Heaven’s Door, his first charting single in many years and one of his most enduring songs, for the film. He became so energized he then recorded his first No. 1 album, Planet Waves, and soon embarked on Tour ’74, his first coast-to-coast series of concerts in eight years, a hugely lucrative tour that even landed him on the cover of Newsweek.


Bob Dylan's Philosophy As Seen Through His Lyrics:

• Gain perspective about yourself with each new day.
I was so much older then/I’m younger than that now.
(My Back Pages)

• Don’t idolize people just because they’re rich, famous or powerful.
Even the president of the United States sometimes must have to stand naked.
(It’s Alright Ma)

• If you do the right things and make the right decisions, your life will be sweet.
May your heart always be joyful/May your song always be sung/
And may you stay forever young.

(Forever Young)

• You must be true to yourself, even at the expense of alienating the crowd around you:
The man in me will hide sometimes/To keep from being seen/
But that’s just because he doesn’t want to turn into some machine

(The Man in Me)

• Change with the times, or you’ll be left behind.
And you’d better start swimmin’/Or you’ll sink like a stone.
(The Times They Are a-Changin’)

• Sometimes you just have to keep showing up, putting one foot in front of the other.
The only thing I knew how to do/Was to keep on keepin’ on
(Tangled Up in Blue)

• Do not be fooled or blinded by material possessions at the expense of having lifelong ethics.
Money doesn’t talk; it swears
(It’s Alright Ma)