The Road to Power: 65 Jobs and No Clear Path

Early Life and Shaping Experiences

Below is the initial stage of my research and notes for the upcoming Robert Greene episode on Club podcast.

*Robert Greene Freshman Year (Source: X Robert Greene)*

"I didn't write The 48 Laws of Power until I was almost 40. Before then, I had lots of failures… I know what it means to not make it in life. I know what it means to suffer. I know what it means to feel bad about yourself, to even feel depressed and suicidal. I know how that feels. And I never want to lose that, no matter how successful I am." — Robert Greene 2024

Born May 14, 1959

Grew up in Los Angeles, in a neighbourhood called Baldwin Hills.

“My parents left me alone. Many times my sister almost raised me in some way and I had a very nice childhood, quite alone”

“I became an avid reader at an early age. I knew I wanted to be a writer.”

“I had an attitude or a way of seeing people from a distance as if always I was obsessed with it. People used masks, so I saw it. Even when I looked at my parents and friends and said, What is really happening behind the masks that they have and all the social jokes that happen? What is behind it?”— Greene, R. (2023) The Diary of a CEO: "How to seduce anyone, build confidence & become powerful E232". [Podcast] 23, March 2023.

For Robert Greene, the key characteristics that contribute to his success are 'Emotional Intelligence,' 'Curiosity,' and 'Anger.'

Emotional Intelligence, a skill sharpened through a lifetime of experiences and setbacks. Having worked in approximately 65 different jobs, Greene was exposed to a vast range of workplaces, power dynamics, and personalities, giving him an unmatched ability to decode human behaviour.

*‘The 48 Laws of Power’* Well, here in the United States, more than 2 million copies have been sold, which is great. The strange thing is that now it is selling more than ever before in other words the percentage of books we are selling here in 2023 is greater than in any period’ *Translated in to 30+ languages”—(Greene.R 2023)* ***HERE***

Greene has spoken extensively in YouTube interviews about the importance of finding your ‘unique purpose’, —what the ancient Greeks called your daemon, an inner voice that guides you toward your true calling.

“The way to recover the meaning of life and the worthwhileness of life is to recover the power of experience, to have impulse voices from within, and to be able to hear these impulse voices from within — and make the point: This can be done.” — Abraham Maslow "Meaning of Life : According to the Great and the Good". Book by Richard T. Kinnier, 2007.

Robert’s own path was anything but clear. His early career was filled with uncertainty, bouncing between over 65 different jobs with no sense of direction. It wasn’t until the age of 40 that he wrote The 48 Laws of Power, finally aligning his experiences, knowledge, and innate instincts into something truly transformative. His journey serves as proof that purpose isn’t always discovered early—it’s shaped through struggle, experience, and relentless curiosity.

These experiences didn’t just shape Greene’s perspective; they became the foundation of his book The 48 Laws of Power and his ability to empathise with those who feel lost or disillusioned, “I know what it means to not make it in life. I know what it means to suffer.”

Unlike traditional self-help authors who preach blind optimism, Greene offers something far more profound—a psychological roadmap that dissects the hidden dynamics of power and influence. His books don’t just inspire; they equip readers with the tools to navigate the unspoken rules of life, master a skill, and become indispensable in a world where everything feels replaceable.

The Sublime

For years, Greene had wanted to write about the sublime, but a near-death experience—a stroke that nearly took his life, the incident occurred on August 17, 2018, while Greene was driving with his wife gave the book a deeply personal dimension; "I came just an inch away from dying," he recalls. "I felt it in my bones, that brush with the ultimate limit. And that experience changed the way I see the world. Now, I can write about the sublime not just intellectually, but from something deeply felt."

"Being human means living within certain social codes and conventions," Greene explains. "These boundaries shift over time, but they always exist. Yet, we are naturally drawn to what lies beyond them. That pull toward the unknown—whether it's an idea, an experience, or even the ultimate limit of death itself—is both thrilling and terrifying. And that’s the essence of the sublime."

Over the years, Greene has meticulously shaped the book, refining its chapters down to twelve core themes. But beyond the academic exploration, there’s also a spark of defiance driving his work. "People’s worlds have become so small, so programmed, so banal. They disappear into their phones, living inside an algorithm. Nothing in our culture provides the kind of awe we instinctively crave."

With The Sublime, Greene wants to rekindle that lost sense of wonder—the kind of awe once found in religious experiences, but without the structure of organised religion. He envisions the book as something almost sacred in its impact, a modern scripture for those seeking meaning beyond the digital void.

Greene has spent decades helping readers decode power and influence. Now, he’s leading them toward something even greater: a rediscovery of the limitless, terrifying, and extraordinary potential of human existence.

"The inside of this book, in a way, resembles the inside of a Bible, the Quran, or the Torah."
Many have noticed a striking coincidence—the inside of some of Greene’s books resemble the layout of holy texts like the Bible, Quran, or Torah. Interestingly, Greene himself has reflected on this, speculating that it may have stemmed from his early experiences with the Torah. As a child in Hebrew school, he recalls studying passages that were accompanied by interpretations, a format that seems to have unconsciously influenced the structure of his own work. Whether intentional or not, this resemblance adds to the almost scriptural weight of his writing, reinforcing its role as a guide to understanding human nature and power.

At the heart of Greene’s work lies a deeper mission: to make reading, studying the classics, and exploring philosophy "hip" again. In an age of constant digital distraction, Greene hopes to inspire young people to step away from the screen and challenge their minds. With the rise of Stoicism and a growing hunger for intellectual depth, perhaps his vision is finally becoming reality.

Ways you too can improve Emotional intelligence:

“Making a name for oneself in any creative industry is notoriously tough, and the road to publication is rarely smooth. More than eight percent of young adult authors reported being rejected one hundred times or more by a publisher before securing their first book sale, and many authors struggle to sell their books even with the help of a literary agent.” (Statista)

I wanted to make history exciting for people, particularly for young people, to kind of make them realise. that it's not just a bunch of dead facts it's exciting and it also teaches you incredible lessons about the present what would you say

“the judging moralistic writer is looking down on the reader. I don't want to tell people what to think. I want to guide them into thinking it on their own. (Greene .R 2024).

I genuinely feel, I don't have a very high opinion of myself, to be honest with you. It goes back to my childhood, whichever. You know, I never did well enough in school, even though I was a straight A student. Parents were, you know, but more and more and more. I never felt comfortable about myself Right? Yeah. And I had a lot of failure when I was younger. This is before you wrote 48 Laws. I didn't write 48 Laws until I was...basically almost 40 when it was published. And before then, I had lots of failure. I mean, I did fairly well, but I never had any.

I never had a job for more than 11 months. So I know what it means to not make it in life. I know what it means to suffer. I know what it means. to feel bad about yourself, to even feel depressed and suicidal. I know how that feels. And I never want to lose that, no matter how successful I am.

So I don't want to talk down to readers, but I actually also feel great empathy for people who have to work in bad jobs. Don't feel Like they've understood their life's task to quote something from mastery. I'm being authentic in that feeling. I really empathise with people and what they're going through in this world.

Personality

Jordan B Peterson:

“You have a very gentle demeanour and a very...soft and kind voice and you don't look like a harsh person.

cardinal personality dimensions:

There's five of them.

extroversion, which is a positive emotion, and it's associated with assertiveness and enthusiasm.
And Trump is extroverted.
Negative emotion, that's neuroticism. And that's the whole panoply of negative emotions. They all clump together and people differ in their sensitivity to them.
Agreeableness, that's compassion and politeness on the high end and more like bluntness and competitiveness on the other end.
and conscientiousness and openness which is creativity you're obviously high in openness you're entrepreneur you're a writer you're interested in ideas you're obviously creative but you strike me as someone who's very high in agreeableness, compassion, that's compassion and politeness. Is that a reasonable? observation?”

Robert Greene replies:”I think that's fairly spot on”

Jordan Peterson: “so is it possible i don't want to push this interpretation beyond its reasonable limits but i'm i'm wondering you're you're, open and creative and entrepreneurial. And so that's not gonna suit you for managerial or bureaucratic jobs. You don't have the temperament for that. And then you're agreeable. And so-Is it possible that you encountered more of that bullying behaviour, or like a disproportionate amount of that bullying behaviour and so forth in the jobs that you had?

Robert “I think that's very possible. And yes, and I'm also very sensitive. So I'm kind of, you know, react a little bit more than most other people might react. But the odd thing is that the book came out in 1998 and it has resonated with lots and lots of readers. I've sold millions of copies of the book.." And so I think a lot of people share the trait that I have.”

Robert Greene believes his books resonate because they offer a level of brutal realism that most self-help and business books avoid. While mainstream culture promotes the idea that success comes purely from cooperation and positivity, his work acknowledges the hidden power struggles and darker human instincts at play. Readers are often shocked at first but also drawn to the honesty—it taps into a “shadow side” of human nature that society tends to suppress. That sense of taboo, almost like holding a forbidden text, adds to the book’s appeal, making it feel both insightful and exhilarating.

Career

Although many cite him having worked over 80 jobs it’s more like worked 60-65 jobs.

“So you quoted me, I had like 80 different jobs, probably more like 60, 65. But I saw all kinds of very… deceptive games being played continually in the various different jobs I had. And I worked in every conceivable field.” (Greene. R 2021)

Job roles in no particular order include:

Magazine editor
lived in New York after college and worked in journalism. And didn't really like journalism.
and then i wandered around europe for many years and i tried to write novels i didn't have discipline didn't work and i was broke
then my fatherwas not well. I'm from Los Angeles. And I had been teaching English in Spain at the time. And I came back here.
through my sister, who was like a typist for a film director, I got a job pretty quickly. In the business, I was an assistant to a director and to his wife, who was a screenwriter. Very nice, very wonderful people.
honed some of my my researching chops there but the main thing was to write screenplays and i wrote screenplay
translator
Journalist
Writer at Fabrica (art and media school in Italy)
construction worker
Teacher
Telesales representative
Hollywood screenwriter

“I came out of college and I wanted to be a writer and I had all kinds of romantic notions of what that meant. And then I entered journalism and I worked in New York.”

“I didn't find that that was a very good fit.”

“Moved to Europe and I wandered around for four or five years writing, trying to write novels and working in hotels, doing construction. kind of the writer's life where the variety of experiences were kind of giving me material. And I couldn't, I never was really...”

“in Nicaragua. I was a journalist. I was covering the civil, the revolution, the civil war going on”

Robert pitched a book packager an idea about power while working at an art school in Italy, and that idea eventually became The 48 Laws of Power, his breakout success.

Networth

He makes money through writing, motivational speaking, and YouTube content creation.

‘unknown.

Partner Anna Biller Guest on Polyester Podcast

New book Sublime:

You know, the ultimate and sublime is to me. So the way I look at it is being a human being and being socialized.

There's a kind of a world, there's a limit, a circle that we have to live inside. Certain codes and conventions that we have to abide by. And we all do that. And the codes and conventions.

For 5th century BC, China are not the same as what we have now, but there's still that limit.

Humans are attracted to what lies beyond that limit. It's just part of our nature. It's the first part of it. And when we explore beyond the social limits and codes and things,

supposed to do and ways we're supposed to act. It's deeply exciting and thrilling. There's also that element of fear involved, right.

It was in the aftermath of that devastating experience that you decided to turn particularly to the sublime.

Yeah. Well, it's because I've been wanting to write the book for a long time, and I knew that it has to do a little bit with the feeling of death.

Well, because that limit and experiencing the limit gives you that sense of... excitement and fear at the same time. Well, death is the ultimate limit. To have gone up to that door and glimpsed to the other side and literally felt it in your bones and literally feel your bones melting away as you...kind of go into a coma you know is like i went up to that door i actually

peered inside of it now other people have had much stronger near-death experiences mine was more of the milder sort but still i peered as far as as far as nearI've been meaning to write this book for 15 years and I got distracted. But then about three years ago, I nearly died myself. I had a stroke.

And I came just an inch away from dying myself. I was driving my car.

And so some of the experience, the near-death experience and what it kind of taught me and how it sort of remained with me three years later and how I kind of feel it in my bones.

and how it's altered how I look at the world and everything around me is to me the kind of the ultimate sublime experience. So now...

Unfortunately, I'm able to write about this in a way that's actually very personal and experiential instead of just purely intellectual.

I know all chapters by now. Yeah. Because when you have the note cards, you organize them into themes and those themes become your chapters. And I started off with maybe...20 some chapters for this book they're now 12 because i whittled them down.

Well, yeah, a lot of the impetus for the book is another little bit of anger as well. So I always have to have some anger in order to...

feel the you know the impulse to write and just discipline myself and

My anger now is about how people's worlds have become so tight and so banal and so limited.

where they're just kind of disappearing into their phones and their world is just sort of programmed for them by..

“I kind of want to spark a sense of almost the religious awe without an organized religion behind it. Because I think...

We have changed a lot in thousands of years, but there's something in our nature that kind of craves those kinds of experiences and nothing in our culture is providing it. It's the definition of crave. I don't think nothing music does.”

The inside of Robert’s book actually do in a way sort of resemble the inside of a bible or Quran or Torah. (See below)

“
I don't know quite where this comes from, but there were like, sometimes there were a couple of things. I'm Jewish, I went to Hebrew school. In Hebrew school, you had passages from the Torah that you had to...learn and that were relevant for your particular bar mitzvah. And I remember in the Torah, there would be like an interpretation of that passage. I don't remember if it was on the margins or not. You know, obviously the Torah you're reading, it's in Hebrew. Right. But... So, and maybe the interpretations were in English.

So I thought maybe comes a little bit from that.