Waterskiing with Bob Dylan

Season 4, #1: How to stay curious (in your life and work)—and wipe out indifference

“To each his own, it’s all unknown/If dogs run free.” 

— Bob Dylan

NOTHING WAS MORE PLEASING during last summer’s horrific global pandemic than outdoor walks with my K-12 teacher friend Chris. Since he was off for the school year, he was feeling expansive and I — well, while I was able to hold down my job remotely, I still needed to get away from all the screen time.

Sometimes we biked or, if it was too hot, we’d take circuitous walks around the neighborhood and chat about arcane music history. At the time I was toying with a podcast about songwriting, since singer-songwriters (more solo artists than members of a group) were a subcategory that particularly interested me, mainly because if you’re in a band and it breaks up, you’re likely back out on the street “trying to form a new band.” It seemed like way too much trouble. Artists like Carole King, James Taylor, or Jackson Browne struck me as “self-contained” — that is, the band was inside them: concept, vision, style and all. If the band inside them “broke down” (as I’m sure they had moments when the creative well ran dry) they had no one to blame but themselves.

I liked that idea a lot — it was something I could relate to.

On one walk Chris and I were joking around and trying to one-up each other with the most bizarre music history factoid we could recall. We’d both seen a recent documentary about the Laurel Canyon scene in the 1960s and ’70s, about Joni Mitchell and fights between Crosby, Stills, Nash and Young, but then I remembered a story told to me by one of my old screenwriting buddies (who for the purposes of this article asked to be called “Diego”), probably during our weekly script group sessions in the 1990s.

Instantly I felt I’d hit the brass ring. “So,” I said, “one of my friends went waterskiing with Bob Dylan.”

Chris stopped, doubling over with laughter.

“ — Wait, WHAT?!”

“Yeah, that’s what my buddy Diego told our script group, probably when we were taking a break and fishing around the table for celebrity stories.”

Chris tried to contain his chuckling. “I can’t even picture that. So…how did that happen?”

“Well, it was when Diego was young, probably in the late 1970s or early 1980s…I’ll have to follow up and get the deets from him.”

“Could you? I’ve gotta hear this story!”

So, during the COVID-19 summer that seemed forever, I phoned Diego and had him relate the story in more detail — twice actually — since the first time I just listened and the second time I prepared questions ahead and took notes.

I say all this because these are practices that anyone can use in their life and career to more fully enjoy all the amazing stories the world has to offer. The core secret of the practices?

Curiosity.

You see, during the pandemic I was in a brain fog. Even though I never contracted the virus and continually tested negative, I later learned it was psychologically part of the way the coronavirus was messing with human brains. Along with the brain fog, I also experienced loss of appetite and rampant incuriosity. That last symptom really did a number on me because I’ve always been a curious person. I love questions. Questions can move mountains; questions get to the heart of things. When my teacher friend got curious, he renewed my curiosity.

And when you go down a particular rabbit hole you discover more about yourself and others than you would ever think possible. Conversely, when you’re fighting through cobwebs of indifference, it can feel like you’ll never escape. That’s the lie it wants you to believe. When you start with the basic questions, then follow-up with more questions, you start to get answers — which may lead to more questions. Which is not a bad thing. It gets things closer to the truth.

So let’s cut to the chase and find out how waterskiing with one Robert Zimmerman can help you be happier and stay curious.

To do that, we need to deep-dive into the source material — Diego — recalling a summer when he was 17 or 18, which we narrowed down to 1981. His family owned a cabin on Maple Lake, just north of Minneapolis-St. Paul, Minnesota. A neighbor on the lake was a guy named Eli, who Diego got to know since they shared a passion for music. When talk came around to musicians they liked, Diego mentioned Bob Dylan. “Well,” Eli told him, “I’ll have to pass that on to him!”

“ — wait. You know Bob Dylan?”

“Have for a long time. He often comes up here with his family in their Airstream and we hang out.”

So, Diego made it known he wanted to meet his idol and Eli promised to let him know when the Zimmermans were paying a visit. That happened during that summer of 1981. Bob Dylan had just put out his latest LP, Shot of Love, and when he and his family, joined by their teenage daughter Maria, visited Eli, Diego was invited over. Dylan wanted to go waterskiing on Eli’s robin-egg blue speedboat. That afternoon it was Diego, Eli, Maria, and Dylan.

I asked him how long they were out on Maple Lake.

“Oh, about an hour or so. He wore black swim trunks, had on sunglasses, smoked occasionally on the boat. We had a BBQ lunch back at the cabin afterward. I got to drive the boat. I wiped Dylan out.”

“ — Wait, you did what?!”

“Yeah, I made him wipe out. We had to go back and pick him up.”

“How did he react to that?”

“As we were pulling him in, he said, ‘Hey what was that?’”

Photo by Claudio Schwarz on Unsplash

Diego and I laughed.

I asked him how Dylan appeared on that particular day, whether he seemed to be enjoying himself among at least one stranger. He was “relaxed and content,” Diego said. “Off the boat and back at the BBQ, I’d brought along a music demo I’d made on cassette and gave it to him, which he took. I said, ‘Man, nobody is going to believe I spent the day with you! Could I get an autograph?’”

Dylan demurred. “No, I don’t do that since they killed John,” he said, referring to Lennon’s assassination that previous December. He accepted Dylan’s decision and the afternoon went on.

My last interview with Diego was on June 5, 2021, so this is all going off the memory of my friend about an incident that occurred exactly 40 years ago. I asked him if he had any thoughts or impressions after that day. He just mentioned that he would never forget it and was grateful he took up Eli’s invitation to join them at the cabin. And a day of waterskiing with a music legend.

For myself, it reminded me of the amazing power of stories, curiosity, and asking questions.

Incuriosity puts up a wall — an unnecessary boundary beyond which it’s possible to discover things you’d never experience on your own. I thanked Diego for taking the time to answer my questions and passed the updated story on to my friend Chris the next time we took a walk.

Which sort of begs another question: “How do you deal with incurious people, then?” Probably the best response is to use enthusiasm and humor to “light a fire” under the incurious person (as Chris had done with me) and awaken their dormant curiosity.

And then again, some people are just chronically incurious and probably best avoided altogether. Spend more time with the people in your life who are curious and open to new ideas.

While curiosity is a first step, some preparation is necessary to “peel back the onion” of the question (to use a tired metaphor, even though I’m more reminded of those Russian nesting dolls) or, in some cases, to get multiple primary sources so you can triangulate facts and form a narrative. Even if it’s just for your own personal enjoyment, like getting the details on a friend’s story, it’s definitely worthwhile. It certainly helped me when I needed it the most, given the craziness of 2020.

Of course now that I’m curious again, what do you think? I’d love to know!

Bob Dylan probably said it best, so let’s give him the last word:

“If dogs run free, then why not we
Across the swooping plain?
My ears hear a symphony
Of two mules, trains and rain.
The best is always yet to come,
That’s what they explain to me.
Just do your thing, you’ll be king,
If dogs run free.”

— Bob Dylan

[Author’s note: Originally published on Medium in 2023.]

---