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Comparing Monk and Musk

Fri, Dec 8, 2023 Read in 11 minutes

After some internal debate, I read Walter Isaacson’s biography of Elon Musk. I wasn’t necessarily excited to read the book, but Isaacson is a strong writer and Musk is so omnipresent in our society that I felt I should better understand one of the most powerful people on the planet. I also thought I could learn something about the tech industry. Isaacson quickly captivated me as a reader, but not far into the book I began to feel icky. Aren’t there other values that matter other than amassing wealth, I wondered? Like kindness and creative expression? Aren’t there other kinds of contributions besides technological ones?

My wife happened to have a copy of Thelonius Monk: the Life and Times of an American Original by professor Robin D.G. Kelley. I thought that an exploration of creativity in jazz would be a great counterweight to Isaacson’s profile of a tech titan. So I read both books at the same time. I had learned about Thelonius Monk in college but struggled to understand his innovations because my ear wasn’t musically trained. I still enjoyed his famous tune Criss-Cross but I didn’t fully “get it.” Could I better appreciate Monk two decades later, I wondered, by reading a detailed biography? And was there something in the story of Thelonius Monk that might be illuminating about Elon Musk, or elucidate my discomfort with extreme wealth and power? Did the two men have anything meaningful in common? If so, what could I learn from them?

Let’s start with the weird coincidence at the start. Thelonius Monk / Elon Musk. Th-elon-ius Monk and Elon Musk. It’s not an anagram, but you can literally find Elon Musk’s name inside Thelonius Monk’s name. (The “u” is out of place.) I should really end my post here.

But I’ll keep going. Thelonius Monk was born in 1917 in North Carolina in the Jim Crow South. He spent most of his life in New York City. An accomplished pianist, he gigged with the city’s best musicians, yet labored in obscurity for much of his career. He built upon contributions by artists like Duke Ellington and Art Tatum and pushed into exciting new musical areas. Specifically, his compositions broke standard jazz chords into their constituent parts, skipping intervals or sometimes revealing only a solitary note from a chord. He also experimented with time signatures. Meanwhile, he expected his band members to swing with a strong rhythm section, even when his piano playing might clink around the beat. Monk was mostly welcomed and appreciated by jazz musicians. (According to Kelley, this was a very diverse bunch, largely African-American, but also Caribbean, white, and even African, with day jobs ranging from custodians to medical doctors.) He became known for his sartorial style, particularly beautiful suits, richly patterned shirts, and snappy hats. Yet Monk struggled to gain popular recognition or make a steady living until his 40s. For over a decade he became a superstar, winning acclaim and traveling the world with his music. But he never became rich - he always needed to work. By the time Thelonius died of numerous ailments in 1982, hip hop was becoming mainstream. For scifi fans, he died just after the Star Wars movie The Empire Strikes Back was released in theaters. Quite a life!

I’m not going to offer a background of Elon Musk because his life is well documented. He’s also still alive, making this inquiry a bit more complicated. Instead I’ll focus on what Musk and Monk have in common.


Monk was bipolar. He would move between frenetic bouts of creativity to catatonic states. He would stay up for several nights and then sleep for days. Meanwhile, he composed on his piano in his apartment in the neighborhood of San Juan Hill the Upper West Side. (It was hard on the neighbors.) His condition was diagnosed late in life and the early drug therapies available at the time inhibited his creativity and presented horrible side effects. Since jazz formed part of nightlife culture, he self-medicated with booze, cannabis, and cigarettes. He tried heroin but amazingly kicked the habit, when many of his contemporaries (Charlie Parker, John Coltrane - many more) could not and died from addiction. Playing until 3 or 4 in the morning at jazz clubs and moving between cold winter air into smoky venues also meant that he suffered regular bouts of flu and cold. Jazz in the 40s and 50s was hard on your body and it did not pay well for most musicians, who were bound by strict permitting codes called cabaret cards. 

In Isaacson’s book, Elon Musk self-diagnoses himself as bipolar. He also self-diagnoses as being on the autism spectrum. It’s difficult to know. But certainly his rapid moves from manic intensity to depression suggest he may be neurodiverse. He does not seem to use cannabis (other than a famous podcast appearance), but there are a few reports of him draining Red Bulls for breakfast or to stay awake at night. Nothing in Isaacson’s biography suggests that Musk uses antipsychotic medication or any treatments that might be prescribed for a bipolar person.


Thelonius Monk lived during the Jim Crow South and through the heydey of the civil rights movement. In his neighborhood growing up in San Juan Hill in New York City, ethnic gangs would attack each other on the way to school, so he learned to protect himself and his friends. As an adult, he suffered from racist police brutality. In one particularly horrific incident, he was severely beaten near Wilmington, Delaware because he asked a white receptionist for a motel room. (Even his white friend and patron was charged by police.) He also was beaten or arrested by police when he would fall into his catatonic states, which were sparked by depression or his bipolar condition. Confronting an unresponsive black man, police either assumed he was a threat or tried to remove him from the streets.

Musk grew up at the tail end of apartheid, and Isaacson documents a particularly brutal incident at a summer camp. Having lived in South Africa, I recall Afrikaans friends speaking about the boarding school violence they experienced from their peers. Violence at these schools was a real thing, meant to prepare white youth for defending themselves against black South Africans (and earlier, English colonizers) by toughening them up. Musk was sadly the victim of some of these encounters and suffered a horrific beating by classmates. This incident no doubt shaped him. After leaving South Africa, however, he seems to have lived comfortably in Canada and the U.S. and rarely, if ever, encountered direct violence again. Rather, he seems to have been subjected to a different kind of violence – verbal abuse and manipulation – by his estranged father that continues throughout the biography. 


The term hardcore is hardly original to Elon Musk, but it characterizes his attitude towards building products and companies. He would work all night, sleep on the floor, and keep working in the morning. Personal hygiene was optional. To some, being hardcore exemplified his leadership - that he was on the front lines with his troops, trudging through snowdrifts of code. Another interpretation is that the neurodiversity mentioned above contributed to this need - that in a manic state he needs to provoke a monumental problem that needs solving. Isaacson labels this state “demon mode.” But nonetheless, Musk seems to work constantly or is constantly switched on, even if that means playing a video game all night long in a hardcore way.

Thelonius Monk shared this hardcore quality. Because his gigs might wrap at 2am, he would then go home and start practicing with his friends at 3 or 4 am. He would play constantly, sometimes for days on end, either working through new music or trying out new improvisations or arrangements. This was a different era, one in which jazz was one of the major forms of popular entertainment, and you had to practice like hell to stand out from the talented musicians of the day. I’m not sure how many musical artists I’ve heard in my lifetime who put in anywhere near the amount of practice time that Monk did. This is probably why audiences who caught him at his best - when he wasn’t suffering psychologically - remembered the performance for the rest of their lives. 

Management style

Starting and managing a jazz band in Thelonius Monk’s time took hard work. The band needed to select music, arrange the compositions for the band members, find gigs, publicize, travel, and entertain. Monk was hardcore in that he did not help people learn his music with clear instructions. He would sometimes force them to learn his songs on stage in front of an audience. When one musician asked him if they could rehearse beforehand, he said: “Why do you want to do that, so you can learn how to cheat? You already know how to play. Now play wrong and make that right.”  For some musicians, even gifted ones, this “trial-by-fire” approach was too stressful to keep playing with Monk. It wasn’t worth it. But others thrived under his direction and considered playing with Monk to be like going to music school. By learning on the job rather than in rehearsal, these musicians received a crash course in chord structure, theory, and rhythm. 

It’s now a tech mantra that you must fail forward. Thelonius Monk expounded this philosophy in his music. Instructing a drummer, he explained that he shouldn’t try to keep the best time on every song. There might be someone else who swings better - “You can’t always like every song the best. Another player might like the song more than you, and his beat might be better than your beat.”

Like Monk, Elon Musk is revealed to be a quite unsympathetic manager. He is incredibly knowledgeable on technical topics and business strategy, and yet can be heartless and almost deliberately cruel, firing people for minor disagreements or for challenging his authority. This didn’t just apply to newcomers, but also to long-term, loyal employees and business partners. (As an aside, Isaacson often glosses over the impact on the lives of these employees when they are fired from these high-profile tech jobs. Maybe the author just didn’t have time to follow up on them, but it’s a glaring omission from the story.)

I’d be remiss if I didn’t mention that both men loved to joke around. Monk pranked and played with words, shooting the breeze with friends and family. Musk does the same, according to Isaacson, peppering his days with scatalogical humor and clever turns of phrase. For all their intensity, both of them clearly like to have fun.

Palo Alto

Palo Alto is where Elon Musk famously started his company Zip2 and then PayPal. His immense talent, drive, and access to wealth and power in Silicon Valley, propelled him to become the world’s wealthiest person (at the time of writing this, anyway).

Thelonius Monk visited Palo Alto too, specifically the famed Palo Alto High School. He traveled there in 1968 during a time when the largely African-American and LatinX neighborhood of East Palo Alto - just across the 101 highway from Palo Alto - was renowned for its poverty and violence. In the 60s, there was an effort to rename East Palo Alto “Nairobi”, part of an Africanist movement. Monk traveled down to Palo Alto with a student named Danny Scher in between gigs in San Francisco to play for the high school students, and had a great time. Many black and white students partied together for the first time. Sadly, the name “Nairobi” was voted down in a referendum.

Closing thoughts on charisma

Thelonius Monk spent much of his life poor. Musk became a millionaire in his 20s. Unlike Musk, Monk did not have a father figure in his life (even if Musk’s father comes across as reprehensible.) He lived paycheck to paycheck for many years, sometimes missing meals. But his charisma and commitment to his craft meant that he had a strong kinship network - including his mother, his sister, and his wife Nellie of many decades. “It was his family that kept him sane and provided an anchor,” writes his biographer, Kelley. He also befriended a wealthy patron from the Rothschild family named Nica de Koenigswater who advocated for him and his music. During the good years, Monk traveled the world and visited every continent, and knew that he had contributed to the evolution of jazz music even if he had not benefited financially. It could have been worse - he could have died from the police beatings, or from drug addiction, or from his neurodiversity. But he thrived and contributed, challenging his peers, as Robin D. G. Kelley forcefully argues, to believe in their own creativity. He left behind a beautiful musical legacy. 

Like Monk, Musk’s family seems to sustain him. He has some longtime friends, a supportive mother, and girlfriends and ex-wives who dote on him. While he may not need them financially, he obviously needs this network emotionally - even if he himself may lack basic empathy. Like Monk, he often gathers an entourage around him to advance his vision. People follow him just like they followed Monk, searching for something that they hope he can provide.

Charisma is a complicated thing. It’s almost magical in its ability to persuade people and cannot be easily cultivated. To be charismatic, innovative, and culturally relevant at the same time is even more rare. Monk and Musk both enjoyed this. Charisma can endure, but relevance is evanescent - meaning that there will come a time when society moves on. Monk enjoyed the spotlight for maybe ten to fifteen years. Musk has bathed in relevance for about that long already - we don’t know when society will move on. But inevitably it will.

Monk died at age 65, surrounded by his family and friends. Even though Walter Isaacson’s book is finished, Elon Musk’s story is still being written.

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