I've long admired Billy Oppenheimer’s curiosity and nose for wisdom. Talking to him is a bit like querying an encyclopedia (or LLM) of people, stories, and lessons on making process your north star, rather than outcome.
Billy is a writer and researcher who works with Ryan Holiday and Rick Rubin, and he moves at a different pace than the terminally-online, frantic, instant-gratification culture that dominates today. Spending time with him and circling a small set of timeless truths is remarkably grounding. I hope that comes through as you listen.
If you want to give the episode some love on twitter, it’s here!
I also included a couple of other recs below this week — on The Making of the Prince of Persia and a scene from Good Will Hunting that you need to rewatch.
Dialectic Ep. 29: Billy Oppenheimer -
Attuned to Clues
Dialectic Episode 29: Billy Oppenheimer - Attuned to Clues - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.
18 Favorite Lessons from Billy on Process, Attention, and Becoming
The Work is the Win. Billy’s big idea. In another form, via the Bhagavad Gita: " you have the right to action, not the fruit of that action." Another: ****utterly dedicated and utterly detached. Jerry Seinfeld: “all art is disguising work” and find the struggle you’re comfortable with.
Creativity starts with clues. Rick Rubin’s creative process often begins not with genius inspiration, but by gradually collecting “clues.” Notice what catches your attention, collect them, and give them time to simmer, and see what happens.
Let inputs guide outputs. Similarly, Billy’s newsletter is just the public exhaust of his research work: “I identify and feel more like a reader and researcher. The writing is kind of like: “Here's some cool things I found. Does anyone else think they're cool?”
Be thoughtful with your future self. When highlighting, Billy leaves notes in the margins as affordances for his future self to easily have context on why it was memorable, rather than assuming he’ll remember. Niklas Luhmann calls this “making notes for an ignorant stranger.”
Time is the true filter. Billy: “Whenever someone says, ‘I was reading this morning about…’ I’m like—immediately—I’m out.” He deliberately leaves time between finishing a book and returning to review his highlights, and seeks out idle time to let ideas percolate and linger.
Reading is a divining rod for hidden interests. Joseph Campbell’s line fits Billy’s experience: a paragraph, name, or footnote grips his attention and a path appears that he hadn’t planned. You can't predetermine what will capture your attention. All you can do is follow the clues when they appear.
It’s okay to put a book down for now. Billy’s mindset is: I’m not quitting, “it’s just not for me right now.” Sometimes he’ll come back to it a year or two later, and he’ll be in a different headspace, connecting with it then, often due to personal growth or other reading.
Novelty can be overrated. There is more here, still. As painter Eugène Delacroix said, “What moves those of genius, what inspires their work, is not new ideas, but their obsession with the idea that what has already been said is still not enough.”
Be careful underestimating “little” ideas. One of Billy’s favorite ideas from Mike Nichols: “We don't know what things are. Big things often turn out to be little things, and little things don't walk around with a sign that says, 'This is a big thing.’”
Respect long arcs without comparing timelines. It’s easy to misread someone else’s decade-long competence as destiny or genius and your first-year incompetence as failure. The truth is slower and less theatrical: your talent forms with reps; judgment improves by tossing away what doesn’t hold up. When some performs what seems like magic, ask about their history of compounding.
A bad plan beats no plan. Even failed attempts return data, while analysis paralysis returns nothing. Run a modest plan, make contact with reality, and adjust accordingly. The information you receive from taking action is worth way more than hypothetical, perfect planning. He who hesitates is lost.
Get to boring. The fantasy version of any craft is a highlight reel. Adam Mastroianni’s "coffee-beans test" is a good litmus for whether you really want to do something. Say you want to open a beautiful cafe? What kind of coffee beans are you going to use? What POS system? This applies broadly too; Ben Gibbard, reflecting on his divorce, realized they never got to the boring parts before they got married.
Be great regardless. Harry Belafonte wanted to be an actor, but got stuck singing between scene changes instead of a “real” role. Instead of phoning it in, he "acted as a singer" and took it seriously. Jazz musicians from a local club happened to see his show, stayed after, and brought him to perform at their venue. Be great at whatever you're doing on the way to where you're trying to go for your own dignity, and maybe you’ll get lucky on the way.
The goal post never stops moving. Daniel Day-Lewis nailed this tension while describing his There Will Be Blood character: "You get there and, of course, the world is round. The horizon just keeps receding and receding." The people who've reached what everyone else chases still do the work because they know the satisfaction was never at the destination.
Avoid the catastrophe of success. Tennessee Williams called success "a catastrophe" because comfort removes the very resistance that made you sharp. You must love the process, otherwise, you’re just going through motions in a life drained of necessary friction, like “a sword cutting daisies."
Question your own folklore. Steve Jobs called arbitrary industry norms “folklore” that hold us back. Your personal methods can become a prison. The way you've always done things almost surely contain local maximums, and you most go down to go up.
Work with people whose lives you want yours to resemble. Ryan Holiday looked at people 10-15 years ahead in Hollywood and didn't want their daily chaos. He chose Robert Greene's life instead - reading, writing, and pursuing his specific curiosities. Billy has done the same.
You can choose who you’d like to become. David Whyte says you’re harvesting your identity in how you spend the hours of the day. You're not born to be a director, writer, or anything else. Billy's days are now filled with reading and writing, the very things that once felt like his weaknesses. Who are you becoming?
Description
Billy Oppenheimer (Website, X) is a researcher and writer who works closely with Ryan Holiday and Rick Rubin, and publishes the “Six at 6” newsletter. Billy is also working on his first book, The Work is the Win.
We kick off by discussing one of my favorite new ideas: "looking for clues," a process and philosophy for creativity that Billy learned from Rick Rubin. He shares the story Rick told him when he learned and adopted this language, which is so representative of how Billy (and I!) research in our work.
From there, we talk about Billy's robust research process and how he has created an external brain of the ideas and patterns that inspire him rather than relying on memory. We also talk about the importance of time as a filter and a series of maxims that underpin his work and creativity. We discuss the importance of inputs over outputs and his big idea and book title, "The Work is the Win," as well many related ideas on success, complacency, compounding, standards, initiative, local maximums, and more. We finish with some lessons from Billy's favorite people.
This conversation is a field guide for making things, pushing through the messiness of progress, and attuning yourself to the richness of the world that often takes the shape of clues.
Full transcript and all links: https://dialectic.fm/billy-oppenheimer
Timestamps
0:00 - Intro
1:20 - Looking for Clues with Rick Rubin
17:42 - Billy's Own Clue-Seeking
24:26 - Balancing Listening to the Market and Finding Unique Influences
31:17 - Memory, Notecards, and Billy's External Brain
37:13 - Making Notes for an Ignorant Stranger, or Leaving Clues for Your Future Self
45:09 - Lingering and Time as a Filter
52:51 - Billy's Book and Big Idea: "The Work is the Win"
1:00:07 - Be Great Regardless
1:04:31 - Following Up Even When Your Abilities and Standards Don't Match
1:10:10 - Fending Off the Wolf at the Door (The Comfort of Success)
1:15:55 - Unfolding and Planting Seeds
1:18:17 - Taking Initiative and Opening Doors: "He Who Hesitates is Lost"
1:24:58 - Stupid Bravery and Getting Past the Sewage
1:30:16 - Local Maximums and Resisting Personal "Folklore"
1:36:14 - Some of Billy's Favorites: Ryan Holiday, Rick Rubin, Steve Jobs, John Mayer, Greta Gerwig, Jerry Seinfeld, Ralph Waldo Emerson
1:56:45 - Side Quests
2:02:26 - "I Know What We Do Here" and Creative Environments
2:05:28 - Bringing Familiar and Unfamiliar Together
2:09:26 - Mastery and Compounding
2:12:44 - The Real Life of Appearances
2:15:43 - "Ton-goo-ey" and The Gifts We Give Ourselves
The Making of The Prince of Persia: Journals 1985-1993 - Jordan Mechner
I just finished 'The Making of the Prince of Persia' by Jordan Mechner, published by Stripe Press.
I wrote some thoughts about why I loved it, and why it's such a rare, raw look into the creative journey:
It’s great to read about the nitty gritty of creating something new as it is happening, rather than with the revisionist narrativization that so often comes with memoirs and biographies. Jordan Mechner’s journals are full of personality and life, and yet often substantive on the process too. It’s also a case for the wonders of consistent journaling. Just writing for yourself, having a conversation forward and backward in time, and maybe one day for the world too.
I couldn’t help but laugh at the constant neuroses and yearning to be on another path, whether it be game development and screenwriting or San Francisco and New York and Paris or sequels and new games. It’s a lovely intimate look at the messy progress of becoming, and how sometimes we see things with remarkable clarity, and other times with hilarious hyperbole (to the positive or negative).
Toward the end, I appreciated Jordan’s realization that he has rarely if ever regretted his mistakes of commission (taking too much risk), but has plenty of regrets about his mistakes of omission (being too passive). Jordan's reflection rhymes with what Steve Jobs ends his Palo Alto high school speech in 'Make Something Wonderful' with:
"Now, as you live your arc across the sky, you want to have as few regrets as possible. Remember, regrets are different from mistakes. Mistakes are those things that you did and wish you could do over again. In some you were a fool (usually concerning women). In others you were scared. In others you hurt someone else. Some mistakes are deep, others not. But if your intent was pure, they are almost always enriching in some way. So mistakes are things that you did and wish you could do over again.
Regrets are most often things you didn’t do, and wish you did. I still regret not kissing Nancy Kinniman in high school. Who knows what might have happened? Maybe she regrets it too …"
There’s a funny line toward the end where Jordan almost literally writes, “you can just do things.”
This book is, of course, about the long and winding road of doing just that: creating something from nothing—not because you were given explicit permission or because you were confident you could pull it off (although Jordan is often remarkably sure of Prince’s inevitable success)—but because every person has inside them a bottomless well, waiting to be put to page or code or film.
This is a book that peels back the curtain on the magic and says, why not you, too?
Good Will Hunting (1997)’s Park Bench Scene
I recently rewatched Good Will Hunting after David Perell told me he memorized his favorite scene that happens on the park bench. I love the film but I typically think of "Them apples" or "it's not your fault," or even the ending when I think about the best parts. David is right though. The bench scene is the one:
Sean (Williams): Thought about what you said to me the other day, about my painting. Stayed up half the night thinking about it. Something occurred to me… fell into a deep peaceful sleep, and haven’t thought about you since. Do you know what occurred to me?
Will (Damon): No.
Sean: You’re just a kid. You don’t have the faintest idea what you’re talkin’ about.
Will: Why thank you.
Sean: It’s all right. You’ve never been out of Boston.
Will: Nope.
Sean: So if I asked you about art, you’d probably give me the skinny on every art book ever written.
Michelangelo, you know a lot about him: Life’s work, political aspirations, him and the pope, sexual orientation, the whole works, right? But I’ll bet you can’t tell me what it smells like in the Sistine Chapel. You’ve never actually stood there and looked up at that beautiful ceiling; seen that.
If I ask you about women, you’d probably give me a syllabus about your personal favorites. You may have even been laid a few times. But you can’t tell me what it feels like to wake up next to a woman and feel truly happy.
You’re a tough kid. And I’d ask you about war, you’d probably throw Shakespeare at me, right, “once more unto the breach dear friends.” But you’ve never been near one. You’ve never held your best friend’s head in your lap, watch him gasp his last breath looking to you for help.
I’d ask you about love, you’d probably quote me a sonnet. But you’ve never looked at a woman and been totally vulnerable. Known someone that could level you with her eyes, feeling like God put an angel on earth just for you. Who could rescue you from the depths of hell.
And you wouldn’t know what it’s like to be her angel, to have that love for her, be there forever, through anything, through cancer. And you wouldn’t know about sleeping sitting up in the hospital room for two months, holding her hand, because the doctors could see in your eyes, that the terms “visiting hours” don’t apply to you. You don’t know about real loss, ’cause it only occurs when you’ve loved something more than you love yourself. And I doubt you’ve ever dared to love anybody that much.
And I look at you… I don’t see an intelligent, confident man… I see a cocky, scared shitless kid. But you’re a genius Will. No one denies that. No one could possibly understand the depths of you. But you presume to know everything about me because you saw a painting of mine, and you ripped my fucking life apart.
You’re an orphan right?
[Will nods]
Sean: You think I know the first thing about how hard your life has been, how you feel, who you are, because I read Oliver Twist? Does that encapsulate you?
Personally… I don’t give a shit about all that, because you know what, I can’t learn anything from you, I can’t read in some fuckin’ book. Unless you want to talk about you, who you are. Then I’m fascinated. I’m in.
But you don’t want to do that do you sport? You’re terrified of what you might say. Your move, chief.
