Billy Oppenheimer
Billy Oppenheimer
Curiosity, Creativity, Persistence & Process
Billy Oppenheimer is a researcher for Ryan Holiday. He is also known for his viral long-form tweets and Six at 6 on Sunday newsletter.
Billy is insatiably curious. He is a master at drawing lessons from anecdotes from sports, music, comedy, business, and more.
Our episode with Billy will be arriving in your feed on Thursday, 4 May. In the meantime, here’s an edited version of our pre-interview deep dive into Billy’s ideas and insights.
Background
Links
Website | Six At Sunday Newsletter | Twitter
Themes (each unpacked below)
I. Process & Persistence | II. The Creative Process | III. What Billy Has Learned From Ryan | IV. The Cup of Coffee Theory of AI
I. Process & Persistence
Don’t get caught up with the outcome (Annie Duke calls this “resulting.”) Focus on the process.
“Resulting is using the quality of an outcome to determine the quality of what precedes the outcome. It’s letting the Tony awards or the box office results have sway over your happiness or your satisfaction with the work you did. It’s letting the 0.000017% dictate if the other 99.999983% was good or worthwhile or fun or etc.”
You can’t grow without struggle. You have to love a bit of a struggle.
“Struggling is not always a good thing, of course, but good things are almost always on the other side of a little struggle. It’s good to be in the shade struggling for some light. It’s good to pick up a weight that feels a little too heavy. It’s good to run a little faster than your pace. It’s good to reach a point where you want to quit—it’s a wall trying to keep everyone else out too. Keep going.”
When you are focusing on the process rather than the pinnacle, you are more likely to reach the pinnacle. At one point in 2010 Djokovic wanted to quit. Then he started playing for fun. “The following season, Djokovic enjoyed one of the greatest seasons in sports history.”
Progress is a magnitude of consistency. Keep going.
“Whether it’s getting to the South Pole or freezing the planet over, getting in shape or writing a book, building a company, learning a new language, or perfecting your jump shot—progress is a magnitude of consistency. It’s not how hard you go today, tomorrow, and next week. It’s—when we check in on you in three, four, five, six, seven, eight, nine, ten years—are you still going?”
Panicking is your brain calling you out for not putting in the work. Your emotions are a prediction from your knowledge and experience. When you are calm, this is because your brain is prepared.
Skill is the ability to do something. Talent is the rate at which you can acquire the ability to do something. To get really good at something, you have to be able to pour a tremendous amount of time into it. In order to do this, you need an interest in it.
“Because for most things in life, the prize doesn’t go to the person who shows up with talent, it goes to the person who stays at it the longest. The person who just puts in a tremendous amount of hours. It’s a game of tonnage, you know?”
Minimize “attention residue:” when you switch your attention from one target to another, part of your attention gets stuck with the previous target. You can minimize this by (i) time blocking, (ii) embracing boredom, and (iii) “closing the loop” (completing the task or clarifying how and when you will complete it).
Care, but not that much. “Get over yourself. You’re not that important. Whether it’s the Olympics, the NBA playoffs, a hostage negotiation, or a movie release—care, but not that much. Prepare, prepare, prepare, then show up, and say, who cares?”
Decompose even the most complex tasks into simple inputs. The component inputs are often “so simple as to be trivial.”
II. The Creative Process
One man’s disability is another man’s superpower. Use your unique perspective to see what others can’t see.
““Defects, disorders, diseases, in this sense, can play a paradoxical role,” Oliver Sacks writes, “by bringing out latent powers, developments, evolutions, forms of life, that might never be seen, or even be imaginable, in their absence.” Latent meaning already existing but waiting to be seen. Will you see it?”
Billy believes that creative output is a blending together of elements that previously existed. Ted Gioia has written how this dynamic is essential to the history of jazz.
Creativity is also a matter of taste. See IV. The Cup of Coffee Theory of AI below.
As Andrew Huberman argued, you become creative by creating.
Use time as a filter – over the passage of time, the things you may have once thought of as interesting become dull, and vice versa.
“Put on your art eyes”: listen, look, and pay attention.
“Talking to the comedian Mike Birbiglia, the visual artist Wendy MacNaughton said that the job of the artist is just to “put on art eyes.” “Most of the best drawing in the world,” MacNaughton said, “has nothing to with making a quote-on-quote good drawing. It has to do with seeing what’s right in front of us. I call it, putting on your art eyes.” “That’s what joke writing is too,” Birbiglia said. “The job of a comedian is, like you said, to put on art eyes. It’s listening, looking, and paying attention.””
““Everybody walks past a thousand story ideas every day,” the science fiction writer Orson Scott Card said. “The good [artists] are the ones who see five or six of them. Most people don’t see any.” To see them, put on your art eyes. Pay attention. See what’s right in front of you. Think, could I do something with that?”
Nothing is siloed – expertise gained through specialization is transferable. There exists what Charles Spearman called the “g factor.” For example, Michelangelo was obsessed with anatomy, and this informed his work on the Sistine Chapel.
Creativity comes from boredom. Sit with it. Work with it. Neil Gaiman has stated that this is where his ideas come from.
Embrace breakage. “Jerry Seinfeld likes to say, “I’m never not working on material. Every second of my existence, I am thinking, ‘What can I do with that?’” When your pottery breaks, your shark malfunctions, your ankle sprains, your bedridden or colorblind—think, what can I do with that?”
“Conceptual ancestors:” Prospero was the origin of Gandalf, The Hero’s Journey is the origin of many of our stories, etc. Your creativity is a product of your conceptual ancestors.
“I once asked Ryan Holiday about how developed his unique writing style. He credited his favorite writers. “The key is that no one has the same combination of influences,” he said. “It feels like me because I’m the only person to combine my interests in my way.” (More recently, he said about the success of his books, “I learned it all from Robert Greene.”) It feels like him because he’s the only person to combine his conceptual ancestors in his way. Which is a wonderful technique for being yourself.”
III. What Billy Has Learned From Ryan
Be Aware of the Trajectory You’re On
“We often think, ‘once I get this promotion…’ or, ‘once I get that job title…’ What we should do is look at people past that promotion and with that job title. Does their life look like one you want for yourself? Are they who you want to be? Because that’s the trajectory you’re on.”
You Are The Sum of Your Influences
“I once asked Ryan about his unique writing style. He said he found artists he liked and borrowed from them. “The key is that no one has the same combination of influences as you,” he said. “It feels like me because I’m the only person to combine my interests in my way.””
Production is a Function of Process
“Ryan’s production is a function of a similar process. He has a warehouse of notecards with ideas and stories and quotes and facts and bits of research, which get pulled and pieced together then proofread and revised and trimmed and inspected and packaged and then shipped. If you develop a process and commit to that process, Ryan says, books come out the other side. They aren’t feats of genius or works of magic or flashes of inspiration. They’re products of process.”
Capture Everything Interesting You Come Across
“Whether your job is to make things with your brain or your someone who can’t start a commute or a workout or a load of laundry without first putting on a podcast, capture everything interesting you come across. Cultivate your external brain.”
Consistent Contributions Compound
“Tim Ferris once asked Ryan to what he attributes his ability to get shit done. This, he said, it’s the cumulative process of making a little progress every day. “Compound interest is one of the most powerful forces on earth. And you can apply that to your own work. Every day, if you wake up and you work on something, you get a little bit closer and it grows.”
You Control How You Respond
“Ryan’s definition of Stoicism is: you don’t control the world around you, you only control how you respond. He’s written about the presumptuousness of the timeless question, What is the meaning of life? As though the world is going to tell you. No, “the world is asking you that question,” he writes. “In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.” That’s how you give life meaning, “and how to turn every obstacle into an opportunity.””
You Can’t Avoid Getting Some of That Mud On You
“Mentors don’t tell you how to do things. They show how they do things. They show you the standards and expectations they hold themselves to. They show you that they eat lunch with a book in their lap. They show you that they step away each day for some strenuous exercise. They show you, when you check your email at 9 am, that they’ve already written one article and put edits in on another. And over time, you might not even realize you got some of that mud on you.”
Stay a Student
One of the great pieces of writing feedback Ryan once gave me was, “Write for a reader who doesn’t know what you know nor care like you care.” The point was that what I wrote assumed a bunch of knowledge and interest on behalf of the reader. “The job,” he said, “is putting these ideas in packaging that makes them useful, interesting, and relevant to people.” The curse of knowledge makes it hard to be good at this and the curse of experience makes it hard to be good at this for long. The antidote is to, as Ryan’s written, “always stay a student.”
Don’t Be Certain
Robert Greene has written that “The need for certainty is the greatest disease the mind faces.”
Jerry Seinfeld tells a lot of jokes. Most of them don’t work. Comedians are amazed when something works. Writing is like comedy. It may not work. Try again.
V. The Cup of Coffee Theory of AI
AI is smarter than Billy. So he’s considered going back to working in coffee shops.
Coffee shops have science’d the process so you can get a great latte, cappuccino, or flat white basically anywhere. Yet people still have all kinds of coffee preferences. These are personal and abundant.
Art preferences are similarly abundant. “So when I hear talk about how AI is going to replace artists, I think to myself, the world is big enough for both. Or when I see tweets about how AI wrote this “great” article or produced this “great” image, I ask myself, “great”—according to whom?””
“This is the perennial challenge of the artist: finding the middle of the Venn diagram where one circle is the artist’s tastes and the other is the audience’s tastes.”
“For the past two years, we’ve tried to hire another research assistant. We’ve trialed dozens of smart, creative, ambitious, book-loving, speedy fact-checking individuals. We always give them a version of the same assignment: read this book (usually a biography) and pull out two good anecdotes and two good quotes. What they come back with is not in the middle of that Venn diagram.”
“In a word, we’ve struggled for two years to find someone with taste—with an eye for what stands the chance of being interesting, entertaining, or useful to an audience.”
Taste is about choosing what you are going to do and what you are not going to do. ChatGPT is not good at this. It is not good at discerning and choosing what to do and what not to do.
Whenever you release art into the world, you can’t forecast its reception. The best you can do is have a vague sense that others might like it. People are better at these types of guesses.
“AI, completely detached from reality, will have a hard time making things that connect with people. It’s something of a hybrid between the Harvard grad student in the movie Good Will Hunting, who can regurgitate page 98 of Daniel Vickers’s Work in Essex County but can’t come up with any thoughts of his own, and Will Hunting, who can give you the skinny on Michelangelo—life’s work, political aspirations, his relationship with the pope, sexual orientation—but can’t tell you what it’s like to stand in the Sistine Chapel and look up at that beautiful ceiling.”
AI “can’t be certain that your work (or its own) will connect with the human experience. It can’t be certain that the work will land in the middle of that Venn diagram. It can’t be certain that its taste and discernment are “great.” This remains the perennial problem of making great art.”
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Loved this! Looking forward to the podcast! When I saw Billy's work, I instantly thought Jim should have him on the podcast and alas Jim was already on it. I'm excited for this one!