IN-DEPTH: Systematic Depth (w/ Ryan Holiday)

Cal Newport introduces his new podcast series, IN-DEPTH, explaining its infrequent release schedule and minimal advertising. He then introduces his guest, Ryan Holiday, a New York Times bestselling author, whose new book, "Right Thing Right Now," focuses on the Stoic virtue of justice. The episode will explore the importance of justice in cultivating a deep life, a concept often overlooked. The conversation will also delve into Ryan's personal journey, from dropping out of college to becoming a prominent figure in the Stoicism movement, analyzing his mindset and decision-making process throughout his career.

The conversation begins with Cal congratulating Ryan on his latest bestseller. They discuss the somewhat arbitrary nature of bestseller lists and the disconnect between list placement and long-term book success. The discussion transitions to Ryan's new book, "Right Thing Right Now," focusing on the Stoic virtue of justice. Ryan explains why he avoided using "justice" in the title, as it can be perceived as judgmental or moralistic. He prefers a more practical definition: living by a personal code of conduct, being honest, treating others well, and striving to make the world a better place. Cal introduces the concept of a personal "code," emphasizing its importance as a guiding principle in life, similar to a boat's keel providing stability. They discuss why defining a personal code is increasingly challenging in today's pluralistic society, where differing values make it difficult to establish universal moral standards.

Cal poses a scenario of a 25-year-old with professional ambitions but lacking a defined moral code. Ryan suggests that without a code, ambition can lead to questionable decisions prioritizing career advancement over ethical considerations. He emphasizes the importance of considering the long-term consequences of actions and aligning them with one's personal values. They discuss the often-overlooked value of making sacrifices that align with one's principles, even if they result in short-term negative consequences. Cal shares a personal example of turning down a lucrative speaking engagement due to ethical concerns, and Ryan relates a similar experience. They agree that these sacrifices, while difficult, are incredibly rewarding and contribute to personal growth and resilience.

The conversation shifts to Ryan's personal story, beginning with his decision to drop out of college. He explains his desire to become a writer and his aversion to a traditional office job. He chose to learn directly from experienced professionals, working in Hollywood and as a research assistant for Robert Greene. Cal explores the dual motivations behind his choices: pursuing his writing aspirations while securing an income source. Ryan discusses his subsequent move into marketing, highlighting his realization that creating and selling are distinct skills, both crucial for success. He explains how his marketing experience, working with various authors and building his own marketing business, provided invaluable experience and connections that proved beneficial later in his writing career.

Cal asks about the factors that led Ryan to publish his first book, "Trust Me, I'm Lying." Ryan attributes it to a combination of disgust with the media system, frustration, and a unique understanding of the industry's inner workings. He emphasizes the importance of having knowledge that others lack, creating a compelling narrative. The discussion then turns to a marketing strategy Ryan employed, involving a deliberately inflated advance figure leaked to industry blogs. He explains that this was a calculated move to generate attention and illustrate the ease with which misinformation spreads in the media, a key theme of his book.

The conversation focuses on the transition in Ryan's career from marketing to writing about Stoicism. He discusses the internal conflict between his marketing success and his critical perspective on the industry, which was reflected in his writing. He explains how his initial foray into writing about Stoicism, with "The Obstacle Is the Way," was a gradual process, initially with modest expectations. The discussion explores his vision for his career during this period, influenced by Robert Greene's success as an independent intellectual figure. Ryan describes his approach as a series of projects, without a fully formed long-term plan, and the slow, steady growth of his author platform.

Cal and Ryan discuss Ryan's move to a 50-acre property in Bastrop, Texas, and the impact on his life. Ryan explains that this move represented a conscious decision to create the life he wanted, independent of his career success. He emphasizes the importance of having the financial runway to pursue creative endeavors without the constraints of high living costs in major cities. The conversation then shifts to the evolution of Ryan's platform, which expanded beyond books to include a newsletter, podcast, and other multimedia content. He explains his strategic approach to leveraging different mediums to reach a wider audience and maximize the impact of his ideas.

Cal and Ryan discuss the concept of ubiquity in building an audience, suggesting that a certain level of recognition is necessary before significant growth can occur. They analyze the growth trajectory of Ryan's platform, highlighting the gradual build-up of audience followed by a period of rapid expansion. Ryan compares his approach to that of the band Iron Maiden, emphasizing the importance of consistent, high-quality work over chasing fleeting trends. He prioritizes sustainable growth and maintaining a balance between expanding his reach and preserving the quality of his work and personal life. The conversation concludes with reflections on the importance of prioritizing personal well-being and aligning one's work with one's values in cultivating a deep life.