The Obstacle is The Way: Ryan Holiday : Wisdom From The Top with Guy Raz Ryan Holiday is one of his generation's most influential thinkers. Many people - from rappers to NFL quarterbacks to corporate CEOS and entrepreneurs - credit his writing for introducing them to the teachings of the stoic philosophers. Holiday's books like The Obstacle Is The Way, Ego Is The Enemy, and Stillness Is The Key aren't just popular, they're also respected by historians and scholars. But, he wasn't always a successful writer. Holiday started his career as a marketer — which became the topic of his first book.