#050 - Billy Oppenheimer on Writing, Research, Boredom, & Putting in The Work
Jan 18, 2024
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Billy Oppenheimer, writer and research assistant for Ryan Holiday, Robert Greene, and Rick Rubin, discusses research, naive optimism, working with legendary creatives, boredom, curation, creation, and the importance of putting in the work. They also touch on finding a niche, the evolution of his Six at 6 newsletter, and balancing art with audience feedback. The conversation covers topics like taking the next step, fear of not finding the right stories, working with Rick Rubin, and qualities of a good research and writing assistant.
Finding joy in the work itself leads to success and fulfillment.
Approaching opportunities with naivete and optimism can lead to unexpected and fulfilling outcomes.
Researching widely and combining diverse sources fosters fresh insights and creative thinking.
Deep dives
The Importance of Finding Joy in the Work Itself
The podcast episode explores the idea of finding joy and satisfaction in the work itself rather than relying solely on external rewards or recognition. The speaker emphasizes the importance of stumbling into a profession or project that truly excites and interests you, to the point where you would do it for free. It is highlighted that success often comes as a byproduct of genuine passion and dedication to the work, as opposed to chasing external markers of success. The concept of finding one's own version of stoicism, or a personal approach to dealing with challenges and setbacks, is also discussed.
The Power of Naivete and Optimism in Pursuing Opportunities
The episode delves into the role of naivete and optimism in taking risks and pursuing opportunities. The guest shares their experience of reaching out to a well-known author and researcher, Ryan Holiday, despite knowing that he was well-established and received many emails. Their naivete and genuine enthusiasm propelled them to reach out and offer their assistance, without considering potential rejection or competition. It is suggested that approaching opportunities with an open mind and a willingness to learn can lead to unexpected and fulfilling outcomes.
The Significance of Research and Curiosity
The episode focuses on the importance of research and curiosity, particularly in the creative process. The guest, Billy Oppenheimer, shares their approach to research, which involves reading widely and seeking out lesser-known sources and materials. They discuss the concept of 'differentiated inputs' and how combining diverse and unique sources can lead to fresh insights and innovative connections. The guest also highlights the value of curating and organizing research materials to foster creative thinking and ensure a steady stream of ideas and inspiration.
Balancing Authenticity and Relevance in Content Creation
The episode explores the tension between creating content that is authentic and personally meaningful, while also resonating with an audience. It emphasizes the importance of finding the overlap between one's own interests and what connects with others. The guest shares their experience of balancing between staying true to their own style and incorporating feedback and feedback from their audience. The aim is to create content that both reflects personal beliefs and experiences, while also providing value and resonance to a wider audience.
Importance of Finding the Work
Finding the right work is essential, as awards and success come as byproducts of being passionate about the work. The speaker, deep in research, feels overwhelmed but believes there is something valuable in their concept that can help many people. They express anxiety about finding the right concepts, stories, and ideas for their book but are hopeful that they can execute their well-structured idea effectively.
Working with Rick Rubin
The speaker shares their experience of working with Rick Rubin for over a year, assisting him with research and writing tasks. They describe how their initial interest in Rubin's work led to a Twitter thread that caught his attention and eventually led to a call where they discussed ideas and concepts. They highlight Rubin's innovative approaches in his podcast and other projects, as well as his unique ability to remain authentic and true to himself. The speaker considers the opportunity to work with Rubin as a valuable learning experience, expanding their own knowledge and interests.
Billy Oppenheimer writes the Six at 6 newsletter, and has been a writing and research assistant for Ryan Holiday, Robert Greene, and Rick Rubin. We talk about research, naive optimism, working for legendary writers and creatives, boredom, his newsletter, curation and creation, how “the work is the win”, and his first book.
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(00:52) Naive optimism & turning what you're already doing into a job
(03:31) Researching is where he gets his dopamine
(05:30) Combine timeless works with popular ones; triangulate stories
(10:48) His note taking system (adapted from Ryan Holiday & Robert Greene)
(15:19) The evolution of Six at 6; finding your niche & learning the wrong lessons from role models
(23:10) Reading to find excerpts
(26:01) Curation & creation
(31:03) Seeing a mirror in others’ ideas
(34:10) Living in the present
(37:26) Combining a known and unknown
(39:34) Six at 6 themes: deconstructing creativity & putting in the work
(43:06) Balancing the art & audience feedback
(45:15) Don't “step into the character”
(50:02) Taking the next step & writing his first book
(55:45) The work is the win
(58:13) Fear of not finding the right stories & concepts
(01:00:02) Working with Rick Rubin
(01:07:34) Orson Welles & ignorance; Paul Graham & not putting up with BS; authenticity
(01:13:24) Qualities of a good research & writing assistant; get excited by what others find boring
(01:20:50) Doing it because it’s a compulsion
(01:24:10) Find your boredom dopamine
