Robert Greene: The Man Who Read Everyone Except His Father

"I like to think of myself as this rigorously independent person... The shadow is your insecurities and your vulnerabilities that you're hiding from the world. And I'm hiding from the world a kind of scared child."

After his father died in 2004, Robert Greene's mother told him something he never knew.

His father had secretly wanted to be a journalist.

For forty years, the man sold cleaning supplies. Got up. Drove to work. Sold chemical products to offices and factories. Came home. Never mentioned it.

Robert Greene has written six books about how to read people — their hidden motives, their unspoken desires, the masks they wear and the reasons they can't take them off. He's sold tens of millions of copies teaching the world to see what others refuse to see.

He never saw his own father.

That blind spot sits at the center of everything Greene has built. The world's most famous analyst of human nature spent his childhood watching people from a distance because he didn't feel seen up close. "My parents kind of left me alone a lot," he told Steven Bartlett on The Diary of a CEO. "I was basically, my sister almost kind of raised me in a way."

The books came later. The 48 Laws of Power. The Art of Seduction. Mastery. The Laws of Human Nature. Six titles. Tens of millions of copies. Translated into dozens of languages. Banned from prisons. But before all of that — before the notecards, the color-coded research systems, the partnership with 50 Cent, the cult following — there was a quiet kid in Baldwin Hills, Los Angeles, watching adults from the margins and cataloging what he saw.

Eighty Jobs and a Revenge Fantasy

Before Robert Greene was Robert Greene, he was nobody. Aggressively, painfully nobody.

After graduating from the University of Wisconsin-Madison with a degree in classical studies — a background that would later make him the only bestselling self-help author who could cite Thucydides from memory — Greene entered the real world and found it incomprehensible. "I had no idea of how things operated in the real world," he said in his Yale speech, "and I was very much shocked by all of the egos and the insecurities."

He drifted. Construction work in Greece. English teaching in Barcelona. Hotel reception in Paris. Tour guiding in Dublin. Skip-tracing debtors in Los Angeles — a job that required lying to people to track them down, which would later inform The Art of Seduction in ways he probably didn't anticipate.

The number varies depending on the interview — fifty, sixty, eighty. The point is the same. Nothing stuck. "By the time you're 37, 38... my parents are starting to worry about me. I'm starting to worry about me," he told Bartlett. Then, quieter: "Suicidal thoughts are floating in my brain."

He ended up in Hollywood, writing screenplays. The pay was good. The environment was poison.

Directors wielded power against him — "doing whatever they wanted with his writing, or cutting his name out completely." One boss tormented him. He reacted emotionally. She destroyed him for it. Years later, he realized the moment contained a lesson: "I had violated a law of power 12 years before I ever wrote the book. Law number one: Never outshine the master."

Then came the resolution that changed everything.

He would watch the power players around him "as if they were mice in a laboratory, with some distance." Every manipulation, every ego display, every betrayal — noted, cataloged, filed.

"That book came from a lot of pain inside of me, of bad experiences," he told Rick Rubin on Tetragrammaton in 2023. "It came from that kind of power of almost wanting revenge on that world."

In 1995, working at an art school outside Venice, Italy, Greene met book packager Joost Elffers and pitched him the idea: a modern Machiavelli. Not an academic exercise. A weapon forged from two decades of being on the wrong side of power.

The 48 Laws of Power was published in 1998. Greene was 38. The Los Angeles Times called him "a cult hero with the hip-hop set, Hollywood elite and prison inmates alike."

The angry, broke, suicidal nobody had found his life's task. He hadn't become powerful. He'd become something more dangerous to the powerful: the person who could explain exactly how their game worked.

3,000 Notecards and a Fountain Pen

Greene's writing process is not a process. It's a compulsion wearing a system's clothing.

For each book, he reads 300 to 400 complete works — biographies, histories, psychological studies, philosophical treatises. He reads with a pen, making notes in the margins. Then, weeks later, he returns to each book and transfers his margin notes onto 4x6 index cards, each card representing a single important idea. A good book generates twenty or thirty cards. After going through several hundred books, he's holding three to four thousand cards.

The cards are color-coded. For The 33 Strategies of War: "Blue cards would be about politics, yellow strictly war, green the arts and entertainment, pink cards on strategy." He sorts them by hand, sifts through them with his fingers, rearranges and recombines until patterns emerge from the chaos.

"Writing things out by hand has a logic to it," he explained. "When I'm taking notes, when I'm scrawling with my fountain pen on a card — I'm thinking more deeply than when typing on a computer."

He writes two to three hours a day. One hour in the morning, two in the afternoon. A nap in between. Thirty-five minutes of Zen meditation before any of it, sitting in lotus position on black cushions by his window. Then black tea, the New York Times in print, and a breakfast his wife prepares.

The research phase alone can take years. The Laws of Human Nature consumed six years of his life. And he knows there's something unhealthy about it:

"I started this book. All right, Robert, this time you're going to make this book shorter... And then I can't help it. It turns into six years. There's something probably negative in my past about that. It's a compulsion to please people, it's supposed to do more than it's necessary."

That admission — from the Young and Profiting podcast — cracks open something. The man whose entire public identity is built on intellectual self-sufficiency admits the work is driven by a compulsion to prove his worth. Three thousand notecards aren't just thorough. They're a wall.

What is Robert Greene's Personality Type?

Robert Greene is an Enneagram Type 5

Before naming the pattern, sit inside the feeling.

You're six years old. Your mother's anxiety fills the room like weather — you can't see it, but your body registers every shift. "My mother's a very anxious person, and she'll admit it," Greene told Rick Rubin on Tetragrammaton. "And so you absorb the energy patterns of people you were around when you're that young." Your father comes home from selling cleaning supplies. He doesn't talk about what he wanted. Your sister makes you dinner. Nobody explains the rules.

That is the world a Type 5 is born into — not necessarily cruel, but incomprehensible. Too much input, not enough explanation. The core fear isn't spiders or heights. It's structural: that you are fundamentally unprepared for the demands of being alive. That the world will overwhelm you, deplete you, catch you without enough. The Five's response is to stockpile. Knowledge. Distance. Routine. Three thousand notecards between yourself and the chaos.

If I understand everything, nothing can touch me.

Greene doesn't just fit this pattern. He is the pattern given a publishing deal.

He watched before he participated — eighty jobs weren't career exploration but reconnaissance. "I was always watching and observing in these jobs, even if I wasn't consciously aware of it at the time." He looked at his parents' friends and wondered what was behind their masks. He watched Hollywood power players destroy each other. Every observation was filed. Every humiliation became a notecard. Every betrayal became a chapter heading. "It's all material" wasn't a philosophy. It was a survival mechanism.

He described routines as "very liberating and soothing" and unstructured time as "like hell, like a nightmare." The anxious mind needs guardrails — walls to keep the chaos at a distance it can study.

"I want to be independent because I had parents that basically never gave me enough attention." He said it on Diary of a CEO like it was an observation about someone else. It was the confession of a man who built an entire architecture of self-sufficiency — the solitary research, the spartan routine, the emotional detachment — over the wound of a child who didn't feel seen.

He meditates every morning, sitting in lotus position on black cushions by his window, tracking the birds and the changing shadows, using the Insight Timer app to keep time. Forty minutes of stillness. And still, beneath the discipline: "During that meditation, I start going deeper into myself and I begin to realise that I'm just this insane, chaotic creature with all these impulses running through me." Then, quieter: "Even after years of meditation, I have no access to the core of my being. I'm still a mystery to myself."

The fortress has no bottom floor. You can build walls forever and still find chaos underneath.

The 48 Laws of Power wasn't written by a powerful man. It was written by a man who felt fundamentally helpless and decided to reverse-engineer the machinery that kept crushing him.

Under stress, Type 5s move toward Type 7 — scattered, restless, seeking stimulation to escape anxiety. Greene's twenty-year drift across eighty jobs, multiple countries, and dozens of dead-end roles maps cleanly onto this pattern. Before finding his calling, he was a Five in constant stress: fleeing from incompetence through novelty and geographic movement.

In growth, Type 5s move toward Type 8 — decisive, assertive, willing to take action. We see this most clearly in two moments: the 50 Cent collaboration, where Greene stepped out of pure observation into the arena, and the post-stroke recovery, where he chose to fight rather than withdraw. "I wasn't going to let this defeat me," he told Lewis Howes. "Every day is like a battle, but I'm not going to give up." That language — battle, defeat, not going to give up — is Five reaching for Eight.

His wing is 4 — the Iconoclast. "I'm quite a strange individual, I'm actually kinda weird... I'm not like other people." His long-term partner is Anna Biller, an auteur filmmaker whose The Love Witch took seven years of obsessive craft — the kind of intensely individualistic creative a 5w4 gravitates toward. "He has a strong feminine side and I have a strong masculine side," Biller told LA Weekly, "so we balance each other out." The 4-wing adds the emotional depth and literary ambition that separate Greene from a purely systematic thinker. His books aren't just informative. They're designed as literature.

The Two Faces of Robert Greene

Here's what doesn't add up.

The man who wrote "Crush Your Enemy Totally" and "Use Selective Honesty and Generosity to Disarm Your Victim" is, by every available account, one of the warmest people his collaborators have ever met.

Holiday, who dropped out of college at 19 to become Greene's research assistant, described him simply: "Anyone who has ever met Robert Greene knows that he is an incredibly kind, generous and principled person." Holiday noted that Greene's house "is nice but I'm sure he could afford a bigger one," that his car had "a total of like 9,000 miles on it," and that if you call him during the day, he won't answer. Because he's working.

The gap between the writing and the writer is where the Five lives. Greene's dark, Machiavellian voice is where his unprocessed emotional material goes — the rage from Hollywood, the frustration of eighty failed jobs, the childhood pain of not being seen. In person, the social filters remain engaged. A gentler, more searching person emerges.

Greene knows this about himself. "I have to be honest," he told Bartlett. "There is a naughty element in there... Damn it, Robert. You have a dark side. You're a narcissist." And then: "I had to come to terms with my irrationality, my grandiosity, my aggressive instincts."

If I put the darkness in the books, maybe I don't have to carry it around.

"No tears in the writer, no tears in the reader," he told Rick Rubin. He wasn't talking about sentimentality. He was talking about the transaction: you pour your actual pain into the work, and the reader feels something real. The books are dark because their author's inner life is darker than his calm exterior suggests. The writing is the pressure valve.

The Hustler's Philosopher

In 2007, people in 50 Cent's camp contacted Greene. The rapper was a fan of The 48 Laws. He wanted to meet.

Greene didn't know what to expect. What he found was a man who defied every assumption.

"There is something about 50 that's different," Greene said. "There is an energy and I think the energy is his realistic outlook." The man who'd been shot nine times and built a business empire from Southside Queens had a "Zen-like calmness" and a strategic eye that startled the bookish author.

They spent extensive time together. "I went to his house in Connecticut, hung out in Manhattan, went to the VMAs together in Vegas," Greene told Vice. "I saw his private life and business life."

The collaboration — The 50th Law, published in 2009, debuting at #5 on the New York Times list — was significant not just commercially but psychologically. For a man who'd spent his entire life watching from the margins, this was a step into the arena. He appeared on The Today Show, CNBC, BBC, and MTV News. The observer was participating.

What made the partnership work was that both men understood power from the outside. 50 Cent had learned the laws on the streets of Queens without knowing the technical terms. Greene had learned them in the libraries of Nietzsche and Machiavelli without ever having to survive a shooting. Each had half of the picture. Together, they had the whole thing.

"I love rappers because of their stories and where they come from and what they've had to overcome," Greene said. Coming from a man who studied Sun Tzu for a living, this wasn't slumming. It was recognition. The rapper and the scholar were both self-taught students of human nature who'd learned the game because the alternative was being destroyed by it.

A Wasp Sting in the Neck

In May 2018, Greene finished writing The Laws of Human Nature — a six-year project, his most ambitious work. He had high blood pressure. In July, he traveled to New York and forgot his medication.

Back in Los Angeles, he was hiking in Griffith Park when a wasp stung him in the neck.

Four or five days later, the sting became massively inflamed. His neurologist later theorized that the wasp sting released cholesterol that formed a blood clot.

On August 17, 2018, Greene was driving with his wife, filmmaker Anna Biller, when his voice changed. His vision distorted. His sense of time collapsed — one minute felt like ten. His wife told him to pull over. He got out of the car. She pulled him back in. Called 911.

Everything went blank.

What filled the blank was stranger than unconsciousness. Greene later described experiencing "multiple competing selves" — as if the brain's seamless construction of a unified identity had been exposed as exactly that: a construction. The sense of being one person, moving through linear time, dissolved. In its place: fragments. And somewhere in the fragments, a vivid hallucination that he had died — which, he told Andrew Huberman, paradoxically brought him a feeling of peace.

He woke on a gurney. The entire left side of his body was barely functional. His left hand. His left leg. "My left side of my body is completely dead," he told Rick Rubin. "And I'm somebody who is very physically oriented." The man who had spent his life building an intellectual fortress against helplessness was suddenly, completely helpless.

"Just learning to lift your pinky, your fingers, on my left hand requires as much effort as it would take to bench press 200 pounds before, and I'm not joking. I'm trying to lift my pinky and I'm sweating, it's so hard."

"I still can't make my own breakfast, so my wife has been making my breakfast, which is quite a burden on her," he told My Morning Routine three years after the stroke. "I also can't wash dishes, so we have a caregiver here who helps me." He watched classic films at night because he couldn't do much else. He noticed butterflies in his garden — beauty he'd walked past for decades.

Read that again. The man who spent his entire life building a fortress of self-sufficiency — the solitary research, the spartan routine, the thirty-five-minute meditations in lotus position — cannot make his own breakfast. The world's foremost analyst of power dynamics depends on someone else to wash his dishes.

For a Type 5, this is not misfortune. It is the nightmare scenario made flesh.

He fought. Three-plus hours of physical therapy daily. A recumbent bike for two hours. The same determination that powered six years of research on a single book was redirected toward regaining use of his own body. "I wasn't going to let this defeat me," he told Lewis Howes, "because the alternative was losing hope and becoming suicidal. And I wasn't gonna let that happen."

But something else happened too. Something quieter than the fight.

"Losing that half of my personality de-stressed me a lot," he told Rick Rubin. The physical limitation paradoxically reduced his anxiety. It forced a kind of acceptance the meditation had been aiming at for decades.

The man who converted every experience into strategic knowledge looked at what remained and found something different. "I've been given a second lease," he said, "and I have to think about that every single day."

The Sublime From a Chair

Greene is writing a new book. It's called Towards the Sublime.

Not The Laws of Power. Not The Art of War. The Sublime — "that expansive feeling of being alive," as his publisher describes it, exploring everything from the cosmos to childhood to consciousness to love. The final chapter is about death. He calls it "the ultimate sublime."

The man who taught the world how to crush their enemies is writing about wonder. And he's doing it from a chair, because a wasp sting in the neck took away the distance he'd spent his entire life building.

Years ago, he told the Daily Stoic that Seneca's letters read "like a father giving you advice — the way my father never would have been." The man who couldn't see his own father found a dead Roman to fill the gap. Three thousand notecards. Six books. Tens of millions of copies. An empire of knowledge built over the wound of a kid in Baldwin Hills who didn't feel seen.

"It's all material," he used to say.

He said it like it was wisdom. It was also a wall.

Disclaimer This analysis of Robert Greene's Enneagram type is speculative, based on publicly available information, and may not reflect the actual personality type of Robert Greene.