Turn the Tables | Ryan Holiday Reflects on 10 Years of The Obstacle Is the Way
Oct 9, 2024
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In this conversation, Ryan Holiday, a renowned author and advocate of Stoicism, is interviewed by his research assistant, Billy Oppenheimer. They discuss celebrating the 10th anniversary of 'The Obstacle Is the Way', touching on the book's updates and the wisdom it imparts. Ryan shares valuable insights on personal growth through obstacles and the evolving perceptions of Stoicism in today's world. Their dialogue also explores the intricate relationship between success and failure, highlighting how both can foster virtue and resilience in life.
Ryan Holiday emphasizes the importance of revisiting and expanding 'The Obstacle Is the Way' to reflect his personal and professional growth over the past decade.
The podcast discusses how Ryan's evolving interpretation of obstacles highlights their role as opportunities for practicing virtues like resilience and forgiveness.
Incorporating contemporary examples, such as Taylor Swift's journey, aims to address past criticisms and connect the book with a younger audience.
Deep dives
The Convenience of Virtual Therapy
Accessing therapy can often be hindered by busy schedules and logistical challenges, which is why virtual therapy has gained traction. Online platforms offer personalized treatment that allows individuals to meet with licensed therapists from anywhere, eliminating the need for in-person visits. This flexibility enables clients to start therapy more easily and communicate with their therapists via text between sessions. Moreover, these services often accommodate quick sign-ups and matching with appropriate mental health professionals within days.
Reflections on Personal Growth
The speaker reflects on a trip to Brazil, comparing his past experiences to his current self a decade later, particularly in relation to the success of 'The Obstacle is the Way.' He discusses how personal and professional turmoil over the years, including the pandemic and family changes, have shaped his perspectives and writings. Revisiting the book after ten years provided him with insights into his growth as a person and a writer. This new understanding led to revising the book to better reflect his evolved thoughts and experiences.
Rethinking Obstacles
The speaker emphasizes a shift in interpreting the phrase 'the obstacle is the way' from a focus on professional challenges to a broader understanding of personal growth through adversity. He believes that obstacles are not merely setbacks but opportunities to practice virtues such as forgiveness and resilience in the face of difficult people and situations. This evolved perspective aims to deepen the message of the book, suggesting that life’s challenges teaches us valuable lessons about our character. Revising the book involved integrating this more comprehensive view into its narrative.
The Writing and Revision Process
The experience of re-recording the audiobook prompted critical self-reflection on the speaker's past writing style and choices. He acknowledges that over time, he has developed a nuanced understanding of complex topics, which has led to longer, more thoughtful works. This reflection allows for significant edits, including the removal or rephrasing of statements that he now views as overly simplistic or judgmental. He considers the process of revisiting his earlier work a valuable opportunity for growth, enabling him to produce a more refined and relatable narrative.
The Influence of Contemporary Figures
In the updated edition of The Obstacle is the Way, the speaker includes contemporary examples, such as the story of Taylor Swift, to address past criticisms about the lack of diverse voices in his work. He illustrates how Swift faced personal and professional challenges and successfully transformed adversity into an empowering opportunity. By drawing on current figures, he aims to connect with a younger audience and diversify the representation within the book. This approach not only acknowledges past criticisms but also broadens the scope of lessons explored in the text.
Today, the tables have turned as Ryan Holiday is interviewed by his research assistant, Billy Oppenheimer, to talk about the 10th Anniversary Edition of The Obstacle Is the Way. They discussed why Ryan felt it was important to update and expand the book, what stories and pieces of wisdom were necessary to add, and the experience as a writer of revisiting material you wrote 10 years ago. Ryan also touched on the evolving reception of Stoicism and how his perspectives and writing style have changed in the process, providing a deeper understanding of how life's obstacles present us an opportunity for virtue as much as victory.
Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.