The Obstacle is the Way | Ryan Holiday | Talks at Google

TL;DR

Ryan Holiday explains that obstacles can become opportunities for growth by applying Stoic philosophy and focusing on what you can control. He also traces his path from writing about Tucker Max to working with Robert Greene and building a marketing department at American Apparel, emphasizing relationships, extensive reading, and overlapping work as engines of development. Read on for his practical views on adversity, mentorship, learning, and writing.

Transcript

MALE SPEAKER: Thank you all for coming today. We have the pleasure of having Ryan Holiday here at Google to talk to us. I'll give you guys a quick intro to who Ryan is. Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at 19 to apprentice under Ryan Green, author of "The 48 Laws of Power... Read More

Key Insights

• 🪛 Ryan Holiday's success is driven by his multi-faceted approach to learning and growth.
• 🏛️ Mentorship is about building relationships rather than formal requests.
• ❓ Reading is a crucial part of Ryan's job and personal development.
• 🍵 Stoic philosophy provides valuable insights on how to handle challenges and setbacks.
• 🗣️ Conferences and speaking engagements can be valuable networking opportunities.
• 🤞 Luck and being well-adjusted are additional factors contributing to success.
• ✍️ The importance of having something interesting to say rather than just focusing on writing skills.
• ✊ The power of intense focus and dedication to personal growth.

Questions & Answers

Q: What is the main idea of The Obstacle Is the Way by Ryan Holiday?

The central idea is to approach obstacles as opportunities for growth and turn trials into triumphs. Holiday draws on Stoic philosophy, especially the practice of focusing on what you can control when facing challenges and setbacks.

Q: How did Ryan Holiday begin his career?

While attending UC Riverside, Holiday wrote a student-newspaper article about blogger Tucker Max, and their resulting friendship led to an internship for Max's first book. He later worked with Robert Greene and joined American Apparel as a consultant around 2007 before building its marketing department.

Q: How did working with Tucker Max shape Ryan Holiday's career?

Holiday interned on Tucker Max's first book after meeting him through a student-newspaper article. The book sold something like 2 million copies worldwide, and the experience showed Holiday how blogging and publishing were changing the book industry.

Q: What was Ryan Holiday's relationship with Robert Greene?

Holiday volunteered when Robert Greene needed a research assistant, and the arrangement gradually developed into a mutually beneficial relationship. Greene, author of The 48 Laws of Power and a board member of American Apparel, also connected Holiday's publishing experience with his later marketing work.

Q: What is Ryan Holiday's approach to mentorship?

Holiday sees mentorship as a relationship that develops over time, not a formal status someone grants upon request. He recommends contributing something useful first, as he did by volunteering to research for Robert Greene, and allowing the relationship to grow naturally.

Q: What does Ryan Holiday attribute his success to?

Holiday says that several related pursuits can reinforce one another: working with authors taught him about books and blogging, while American Apparel taught him about advertising and media. At one point he effectively held three full-time jobs, compressing years of learning into one or two years.

Q: Why is reading important to Ryan Holiday?

Reading is a fundamental part of Holiday's work as a writer and media strategist. He often reads two to three books a week and treats books as a way to learn from other people's experiences.

Q: What writing advice does Ryan Holiday emphasize?

Holiday emphasizes having something interesting to say instead of concentrating only on writing technique. His own books grew from his experiences in publishing, marketing, and working with controversial or unusual people, including an exposé of the media industry.

Summary & Key Takeaways

• Ryan Holiday started his career by writing an article about a famous blogger, which led to an internship and working with bestselling authors.

• He learned about the changing media landscape and became a media strategist and Director of Marketing at American Apparel.

• Ryan's success can be attributed to his multi-faceted approach, learning from mentors, and his intense focus on personal growth and learning.