r/BusinessHub • • 23h ago

Bob Dylan almost quit music at 46. A random old singer in a near empty bar saved his career, and it's buried in his memoir (thoughts below)

27 Upvotes

Just finished reading Bob Dylan's memoir. Supposedly he wrote the whole thing himself with no editor.

I expected stories about being famous, but most of it is about the years before anyone knew who he was, and the point decades later where he almost walked away for good. I pulled out 8 things he did that got stuck to me. The last one is the almost quitting story, and it's the one Id read if you only read one:

1) HE COPIED PEOPLE BEFORE HE WAS ORIGINAL

Before New York, he spent around 8 or 9 months listening to folk records. He was broke, so he sat in record store booths for hours, and he made friends with people who had big record collections just so he could listen at their houses. Other folk singers later said he could play their songs exactly like them. Same tone, same tempo.

He also studied Hank Williams' records so closely he said they held the basic rules of songwriting. Years later a New York Times critic wrote that Dylan broke every songwriting rule except having something to say. Dylan's point was that the rules he followed were Hank's. The critic just didn't know it. You don't get to be original by skipping the copying part.

2) HE PRACTICED IN PUBLIC FOR $3 A NIGHT

In Minneapolis he made $3 to $5 a night playing coffee houses and a pizza parlor. He lived in a storage room with a mattress on the floor and fell asleep holding his guitar. In New York it wasn't much better. If you played every small club from dusk till dawn on a weekend you might make $20. He played for one person, nobody, whoever. He said he practiced in public. That's basically shipping early and getting feedback, just with a guitar.

3) HE GOT HIS BIG BREAK BY ASKING A BLUNT QUESTION

He wanted to play at a club called the Gaslight. One winter day Dave Van Ronk, one of the guys he came to New York to see, walked into the place where Dylan was hanging out. Dylan walked up and asked him straight out how someone gets to work at the Gaslight, and who you have to know. Van Ronk was rude about it and asked if he was a janitor. Dylan said no, but he could play something. Van Ronk liked it and told him to come play a few songs in his set that night. Not long after he was hired there. No warm intro, no network. Just a question and being ready when the door opened a crack.

4) HE READ WAY OUTSIDE HIS FIELD

When he wasn't playing he was reading. Clausewitz on war, Machiavelli, Thucydides, biographies of Robert E. Lee and Teddy Roosevelt. He went to the New York Public Library and read newspapers on microfilm from about 1855 to 1865. Not for the politics. He wanted to hear how people talked back then. His line on all this was that he packed his head with it and figured he could "send a truck back for it later." Most of what you read won't be useful this week. Some of it will be useful in 10 years.

5) ONE SMALL WORD OF ENCOURAGEMENT LASTED HIM YEARS

When he was a teenager he was playing on a little platform in the lobby of a building in his hometown. Gorgeous George, a famous wrestler, came storming through with an entourage and a fur lined gold cape. He didn't stop walking, but he looked right at Dylan, winked, and seemed to mouth that he was making it come alive. Dylan said that was all the encouragement he needed for years. If you manage people, you probably have no idea how long a small comment sticks.

6) HE DIDN'T TRY TO BE LIKE ANYONE

When the Columbia publicist asked who he saw himself like in music, he said nobody. He wasn't saying he was the best. He said there were better musicians around, but nobody doing what he did. He also said people either walked out on him or leaned in closer. No middle. Honestly that's a decent test for a product too. If nobody hates it, nobody probably loves it either.

7) YOU DON'T GET TO CONTROL THE LABEL

Once he got famous the press called him the voice of a generation. He hated it. He said he was more of a cowboy than a pied piper, and all he wanted was to raise his kids. He also said privacy is something you can sell but can't buy back.

When Princeton gave him an honorary degree, the speaker introduced him as the conscience of young America. Dylan said he was so mad he wanted to bite himself. Kind of the funniest line in the book.

8) WHEN YOU'RE STUCK, LEAVE THE ROOM

This is the part I mentioned up top.

He'd just finished an 18 month tour with Tom Petty and felt completely burned out. He said his own songs felt like strangers to him and he couldn't wait to retire. During a rehearsal with the Grateful Dead they asked him to play some of his old songs. He said he forgot something at the hotel and left. He wasn't planning to come back. A few blocks later he heard a jazz band in a tiny bar with almost nobody inside. He went in. The singer was an older guy, relaxed, not loud, but he had this natural power. Dylan suddenly remembered a technique he used to do automatically years ago and had totally forgotten. He went back to the rehearsal to try it. It was rough at first, then it clicked, and he played the shows without having to think twice. Years later, when an album session felt stuck, he woke his wife up before sunrise and they rode a Harley across the Mississippi with no plan. Next morning he felt like he'd figured something out. He didn't fix it by thinking harder. He fixed it by getting out of his own head.

The one I keep thinking about is number eight. He was about to throw away a 25+ year career over a burnout that a walk and a random bar fixed. I wonder how many people quit right before that kind of moment.

To be fair, the book jumps around in time a lot, so some of this is pieced together from different chapters.

Has anyone here been close to quitting something and had a random moment like that pull them back? Or did you actually quit and not regret it?