How Obstacles Became the Way in Bob Dylan’s Life

👉 Setbacks fueled Dylan’s greatest reinventions—Let it fuel you, too!

Welcome Back to the Daily Dylan Stoicism Series!

In our last email, we introduced the surprising connection between Bob Dylan and Stoic philosophy—how his resilience, reinvention, and focus on what matters mirror the wisdom of the ancient Stoics.

Today, we dive into one of the most powerful Stoic lessons:

"The impediment to action advances action. What stands in the way becomes the way." – Marcus Aurelius

Or, in simpler terms: Obstacles aren’t roadblocks. They are stepping stones.

This is the central idea of Ryan Holiday’s book The Obstacle Is the Way—that the challenges we face aren’t barriers to success; they are the path to success.

And if there’s anyone who has embodied this idea throughout his career, it’s Bob Dylan.

---

High School Heartbreak: Losing Bands, Finding Purpose

Before Bob Dylan became Bob Dylan, he was Robert Zimmerman—a teenager from Hibbing, Minnesota, obsessed with music. Rock ‘n’ Roll had just exploded onto the scene, and Dylan was hooked.

So, like any determined young musician, he formed a band. And then another. And another.

But there was a problem: Every time Dylan put a group together, other bandleaders would steal his musicians away.

He’d start fresh, build something promising—only to have his bandmates lured away to "better" gigs. Over and over again, he lost everything he had built.

“Lead singers would always come in and take my bands, because they would have connections, like, maybe their fathers would know somebody.”

For many kids, this would have been discouraging enough to quit. But Dylan?

He adapted.

Instead of getting bitter or giving up, he realized something important:

🔹 As long as he relied on a band, he was vulnerable to losing it.
🔹 If he played solo, no one could take anything from him.

During this time, he began immersing himself in Folk Music—a sound very different from Rock ‘n’ Roll. Whether it was the raw storytelling, the traditions, or the emotional depth, something in it resonated with him. And while he likely would have found his way to folk music anyway, the reality that he could perform it alone made the transition all the more natural.

“And somebody – somebody I'd never seen before – handed me a Leadbelly record with the song “Cottonfields” on it. And that record changed my life right then and there. Transported me into a world I'd never known. It was like an explosion went off.”

🎯 The Stoic Lesson: When something is taken from you, don’t fight it—find a new way forward.

(You can also check out our series about Bob Dylan’s High School Bands by clicking here!)

---

The 1965 Betrayal That Changed Everything

Right now, Dylan fans around the world are reliving one of his most infamous moments on the big screen in A Complete Unknown—the moment he "betrayed" folk music at the Newport Folk Festival in 1965.

Imagine this: You’re standing on stage, in front of your most devoted fans—the people who helped build your career, the ones who believed in your music before anyone else did.

And then, they turn on you.

That’s exactly what happened to Dylan when he played an electric set at Newport. The folk purists who had worshipped him now booed, yelled, and called him a traitor.

For many artists, this kind of public rejection—from their own audience—would be devastating. Some might retreat, apologize, or try to win back their fans.

But Dylan? He kept going.

It seemed as though the resistance only fueled him, as if he had expected it all along. Instead of retreating, he doubled down on his new direction.

But in reality—was this shift really so shocking?

The Signs Were There—But Many Fans Didn’t See Them

In our first example, we saw how Dylan, back in Minnesota, had spent his early days plugged in and playing electric music. Before he ever became a folk icon, he fronted high school rock 'n' roll bands, hammering out Little Richard and Buddy Holly songs with a fully amplified sound.

That side of Dylan had never really disappeared. And yet, many folk fans had no idea about his early electric years.

What they could have known, however, was that weeks before Newport, Dylan had already begun the transition. His latest album, Bringing It All Back Home, released in March 1965, already featured a full band on one side. The clues were there—he wasn’t hiding it.

But for many in the folk community, seeing it live was different than hearing it on a record. And so, when he walked onstage with an electric guitar and blasted into Maggie’s Farm, they weren’t ready.

And yet, this wasn’t a radical reinvention. It was simply Dylan returning to a part of himself that had always been there.

So, after Newport, he didn’t just play electric that night—he went on to create Highway 61 Revisited and Blonde on Blonde, two of the greatest rock albums of all time.

🎯 The Stoic Lesson: Resistance means you're onto something. The obstacle isn’t a sign to stop—it’s a sign to keep going. Let it fuel you, too!

---

Dylan’s Motorcycle Crash as a New Beginning

Fast forward to 1966. Dylan is on top of the world—commercially, creatively, and culturally. But behind the scenes, he’s exhausted.

Then, he crashes his motorcycle in Woodstock, New York.

To this day, no one knows exactly how serious the accident was—Dylan has always been vague about it. But what we do know is that he used it as an opportunity to step away from the relentless pressure of fame, stepping “out of the rat race”.

For nearly two years, he disappeared from the public eye.

He stopped touring. Stopped giving interviews. Lived quietly with his family, playing music only with his mates from The Band.

Critics thought it was the end of his career. But what was really happening?

Dylan was transforming.

During this period, he wrote and recorded the Basement Tapes—a collection of raw, stripped-down songs that set the stage for a whole new sound in rock music. When he re-emerged, it wasn’t with another wild rock album, but with John Wesley Harding, an understated, almost biblical collection of songs that confused the critics but influenced an entire generation of musicians.

🎯 The Stoic Lesson: Sometimes, the best response to an obstacle is not to fight it—but to step back, regroup, and use it to grow into something new.

---

How to Apply This to Your Own Life

Dylan’s story isn’t just about music—it’s about a way of thinking, a way of handling setbacks that any of us can apply.

Here’s what the Stoics (and Dylan) would tell you to do when you hit an obstacle:

🔹 Don’t take resistance as a sign to quit—take it as a sign to push forward. (If people criticize you, you’re probably onto something important.)

🔹 Sometimes, stepping back is the best way forward. (Like Dylan after his accident, use obstacles as a chance to pause, reflect, and come back stronger.)

🔹 Momentum is everything—keep moving. (Your "bad years" don’t define you. What defines you is whether you keep creating, keep learning, and keep going.)

Every obstacle in Dylan’s life became the way forward.

And the same can be true for us, no matter where we stand in our life.

---

What’s Coming Next?

In the next email, we’ll explore:

📌 The 4 Stoic Virtues and Bob Dylan – How wisdom, courage, justice, and self-discipline shaped his career.

From standing firm in his beliefs to writing some of the most socially conscious songs of all time, Dylan has embodied all four of the Stoic virtues.

See you in the next email.

Keep on keepin’ on,
Daniel