- This is a wide-ranging conversation between Robert Greene (bestselling author of The 48 Laws of Power, Mastery, The Laws of Human Nature, and The Daily Laws) and Ryan Holiday (author of The Obstacle Is the Way, Ego Is the Enemy, Courage Is Calling, and others) about finding your calling, the creative process, mastery, and the deeper meaning of work and life. Both are prolific modern-day philosophers who practice what they preach, and the discussion touches on creativity, virtue, fortune, fame, and the apprenticeship model.
The Creative Process and Inspiration
- Robert describes the origin of The 48 Laws of Power as almost fateful: in 1995, at age 36, in a low and slightly suicidal moment, he met Joost Elffers in Venice, Italy, and improvised the idea for the book on the spot. He says he still cannot fully explain how the book came out of him — it felt like a revelation or “hierophany.”
- He draws on the Latin etymology of “genius” as a guiding spirit, and suggests the creative process involves removing blocks and subduing the ego, becoming a porous receptacle for ideas — similar to Buddhist concepts of letting go of willful striving.
- Ryan and Robert discuss the neuroscience behind creative breakthroughs: intense focused work builds unconscious neural pathways, but the “aha moment” often comes only after stepping away and letting go. Frustration is a sign you are about to turn a corner — unless you give up.
Mastery and Mentorship
- Ryan’s relationship with Robert mirrors the master-apprentice dynamic described in Mastery. Robert was Ryan’s mentor; Ryan started doing research for Robert at age 19. Robert jokes that Ryan has already surpassed him, but keeps “moving the goalpost further and further.”
- Mastery serves as a blueprint for how Ryan developed — learning through osmosis, then coming into his own. Robert believes their books will still be read a hundred years from now.
Finding Your Calling
- The first two sections of Mastery are especially relevant now: (1) identifying your life’s task — what only you can do — and (2) finding a person who is doing that thing or can teach you to do it. Get those two things right and you can afford to get a lot else wrong.
- Robert shares his own path: he knew at age eight he wanted to be a writer. That overall framework pulled him through journalism, unfinished novels, Hollywood screenplays, and disparate skills that eventually converged.
- Many people lack that internal framework and have no connection to what Maslow calls their “impulse voices” — the inner signals of what naturally draws them. Social media makes this harder by creating a homogenizing, infinite-mirror effect and distracting people with outcomes (fame, reputation) rather than the craft itself.
Fame, Fulfillment, and the Apprenticeship Model
- Fame is “the excrement of creativity” (a Bruce Dickinson quote) — a sludgy byproduct. Social media has made fame itself seem like a goal, detached from the work that produces it.
- Robert argues that people often want to have done the thing rather than do the thing — they want the book, the CEO title, the Instagram following — but the real, deep pleasure comes from the act of creating and building something from nothing. We are homo faber, the animal that makes things.
- Ryan reflects on the pandemic as a “hard reboot”: it stripped away background noise and forced hard conversations about what people actually want. He wrote Courage Is Calling as the easiest and most connected book he has ever written. He sees the pandemic’s silver lining in people waking up to the reality that many jobs are “BS” (referencing David Graeber’s Bullshit Jobs) and that life is too short to live in ways that make you unhappy.
Outsiders, Wilderness, and the Choice of Hercules
- Robert is fascinated by outsiders and people whose brains are wired differently — Philip K. Dick, Kanye West — and the question of whether they are seeing reality more clearly or hallucinating. Culture needs outsiders because they see what insiders cannot.
- Churchill said every prophet must go into the wilderness — a period outside power or convention that transforms how you see things. Ryan’s Courage Is Calling opens with the Choice of Hercules: the decision between the easy way and the hard way. Both men have consistently chosen the hard way.
- Ryan observes that many millennials inherited the Boomers’ optimism without the economic tailwinds, leaving them adrift — renting, traveling, with ephemeral relationships and unlimited options but no rootedness. Meaning comes from scarcity and commitment; without those, you are exposed to every strong wind.
Intellectuals and the Big Picture
- Robert worries about a growing divorce between intellectuals and practical daily life in American culture. Academic writing often turns the most transformative subjects into impenetrable jargon, losing all relevance to real life. He contrasts this with figures like William James, who were intellectuals still grounded in everyday reality.
- He finds it frightening that so many people now live in narrow, specialized zones — the blind man and the elephant — each tugging at one part and mistaking it for the whole. Very few are looking at the big picture or staying grounded in basic reality.