Finding the Sweet Spot of Engagement

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
• 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

Links:

• ‎McCartney 3, 2, 1 (2021)
• The Way of the Tracker: The Path of “not this” - Boyd Varty
• Eddie Murphy Is Tracy Morgan's Favorite | Comedians In Cars Getting Coffee
• Poetry Unbound
• When We Cease to Understand the World- Benjamín Labatut
• Fill Up To Pour Out - Billy Oppenheimer

• The Subtle Art of Not Giving a F*ck - Mark Manson
• The Psychology of Money - Morgan Housel
• LeBron James shows off photographic memory
• The Notecard System - Billy Oppenheimer
• Robert Greene
• Mike Nichols: A Life - Mark Harris
• The Journal of Eugene Delacroix - Lucy Norton
• 19. Henrik Karlsson - Cultivating a Life that Fits - Dialectic
• Stadium of selves — Steph Ango
• 8. Steph Ango - Tools for Amplifying Our Light - Dialectic
• The third chair - Henrik Karlsson
• Secrets of the Creative Brain - Nancy Andreasen
• Setting down the snow globe - Jackson Dahl
• Billy on REST
• Face it: you're a crazy person - Adam Mastroianni
• Tennessee Williams – The Catastrophe of Success
• Critique of Pure Reason - Immanuel Kant
• Billy on Constraint, Gide, and Kant's Dove
• ‎There Will Be Blood (2007)
• The War of Art - Steven Pressfield
• Billy on unfolding
• He who hesitates is lost - Joe Rogan & Jordan Peterson
• Unfolding - Henrik Karlsson
• Billy on John Mayer, Huberman
• Steve Jobs on folklore
• The Making of Prince of Persia - Jordan Mechner
• Make Something Wonderful - Steve Jobs
• ‎Lady Bird (2017)
• ‎Frances Ha (2012)
• Billy on Greta Gerwig
• Billy on "I know what we do here"
• The Art Spirit - Robert Henri