Unveiling the Stoic Secrets: Ryan Holiday’s Journey to Becoming a Guru in Silicon Valley | Philosophy Literature

What led Ryan Holiday, a former PR man turned lay philosopher, to become a bestseller giant? His writings on stoic philosophy are cherished by a wide range of individuals, including professional athletes, politicians, and tech CEOs. Tim Ferriss, an investor-entrepreneur, refers to stoicism as the “ideal operating system”. Even entrepreneur-fraudster Elizabeth Holmes used to cite Marcus Aurelius’s Meditations before her imprisonment. Sports stars like James McGee and Garrett Gilkey can quote from Holiday’s book “The Obstacle Is the Way”, while celebrities such as Arnold Schwarzenegger and LL Cool J acknowledge Holiday in interviews.

Stoicism, an ancient philosophy, focuses on four virtues: courage, temperance, justice, and wisdom. Practicing these virtues allows one to attain complete self-control, enabling them to respond calmly to external stimuli without complaining. The philosophy emphasizes that material wealth should hold no significance, despite some of the wealthiest individuals claiming to live by stoicism.

The popularity of stoicism as a way of life continues to grow. Holiday’s numerous books, totaling around a million, have sold over 5 million copies. The Daily Stoic, Holiday’s brand, has amassed 3 million followers across its website, newsletter, podcast, and Instagram account.

In 2019, Holiday achieved the No. 1 spot on the New York Times bestseller list with his book “Stillness Is the Key”. This marked his fourth venture into stoicism after “The Obstacle Is the Way” in 2014, followed by “Ego Is the Enemy” and “The Daily Stoic” in 2016.

Holiday recalls the modest beginnings of “The Obstacle Is the Way”, which initially sold only 3,000 copies in its first week. However, its popularity soared within a year, particularly within professional sports teams such as the Miami Heat and Seattle Seahawks, who adopted his books as guiding principles.

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Holiday addresses the criticism surrounding the adoption of stoicism by wealthy individuals, pointing out that the philosophy revolves around virtue. He questions why studying a philosophy built on virtue would be considered negative, even if some individuals may miss the deeper ethical aspects.

The prevailing interest in stoicism reflects a modern-day quest for meaning and purpose. Holiday suggests that ancient philosophies offer valuable insights into how to lead a good life, especially in a world where traditional structures and beliefs are fading.

Despite his early success, Holiday’s journey was not without challenges. He dropped out of college to pursue opportunities that came his way, eventually leading him to roles in marketing and writing. His experiences, including working at American Apparel, shaped his understanding of success and the dangers of ignoring advice.

Holiday’s evolving perspectives on stoicism have influenced his writings, moving beyond resilience and productivity to emphasize ethics and morals. He acknowledges the need for a holistic approach to the philosophy, not just focusing on personal benefits.

In the realm of politics, Holiday has been vocal about his beliefs, urging his father not to vote for certain candidates. His social conscience, shaped by stoicism, guides his political views and personal values.

Looking ahead to the future, Holiday remains optimistic about the direction of society despite its challenges. He believes that stoicism offers valuable principles for navigating turbulent times, emphasizing resilience and ethical behavior.

Holiday’s journey exemplifies the intersection of ancient philosophy and modern life, highlighting the enduring relevance of stoicism in today’s world.