I dislike the culture that glorifies self-made man, because I think far too many self-made men are unethical psychopaths.
I present a long quote from a website below. Understand that the original website praises these books, but I present them with great caution, because I suspect that they teach various unethical approaches to ambition.
The Power Broker by Robert A. Caro. It took me 15 days to read all 1,165 pages of this monstrosity that chronicles the rise of Robert Moses. I was 20 years old. It was one of the most magnificent books I’ve ever read. Moses built just about every other major modern construction project in New York City. The public couldn’t stop him, the mayor couldn’t stop him, the governor couldn’t stop him, and only once could the President of the United States stop him. But ultimately, you know where the cliché must take us. Robert Moses was an asshole. He may have had more brain, more drive, more strategy than other men, but he did not have more compassion. And ultimately power turned him into something monstrous.
Titan: The Life of John D. Rockefeller Sr. by Ron Chernow. I found Rockefeller to be strangely stoic, incredibly resilient, and, despite his reputation as a robber baron, humble and compassionate. Most people get worse as they get successful, many more get worse as they age. In fact, Rockefeller began tithing his money with his first job and gave more of it away as he became successful. He grew more open-minded the older he became, more generous, more pious, more dedicated to making a difference. And what made Rockefeller stand apart as a young man was his ability to remain cool-headed in adversity and grounded in success, always on an even keel, never letting excessive passion and emotion hold sway over him.
The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen. This book tells the incredible story of Sam Zemurray, the penniless Russian immigrant who, through pure hustle and drive, became the CEO of United Fruit, the biggest fruit company in the world. The greatness of Zemurray, as author Rich Cohen puts it, “lies in the fact that he never lost faith in his ability to salvage a situation.” For Zemurray, there was always a countermove, always a way through an obstacle, no matter how dire the situation.
[Editor’s Comment: I think United Fruit was associated with dire human rights violations … probably this CEO was a psychopath… and this book might be more of a cautionary tale of hubris rather than a lesson in achievement.]
The 48 Laws of Power by Robert Greene. It is impossible to describe this book and do it justice. But if you plan on living life on your terms, climbing as high as you’d like to go, and avoid being controlled by others, then you need to read this book. Robert is an amazing researcher and storyteller — he has a profound ability to explain timeless truths through story and example. You can read the classics and not always understand the lessons. But if you read the The 48 Laws, I promise you will leave not just with actionable lessons but an indelible sense of what to do in many trying and confusing situations. As a young person, one of the most important laws to master is to “always say less than necessary.” Always ask yourself: “Am I saying this because I want to prove how smart I am or am I saying this because it needs to be said?” Don’t forget The Prince, The Art of War, and all the other required readings in strategy. And of course, it doesn’t matter how good you are at the game of power, without Mastery it’s worthless.
Steal Like An Artist by Austin Kleon. Part of ambition is modeling yourself after those you’d like to be like. Austin’s philosophy of ruthlessly stealing and remixing the greats might sound appalling at first but it is actually the essence of art. You learn by stealing, you become creative by stealing, you push yourself to be better by working with these materials. Austin is a fantastic artist, but most importantly he communicates the essence of writing and creating art better than anyone else I can think of. It is a manifesto for any young, creative person looking to make his mark. Pair up with Show Your Work which is also excellent.
Status Anxiety by Alain de Botton. Ah yes, the drive that we all have to be better, bigger, have more, be more. Ambition is a good thing, but it’s also a source of great anxiety and frustration. In this book, philosopher Alain de Botton studies the downsides of the desire to “be somebody” in this world. How do you manage ambition? How do you manage envy? How do you avoid the traps that so many other people fall into? This book is a good introduction into the philosophy and psychology of just that.
What I Learned Losing a Million Dollars by Jim Paul and Brendan Moynihan. There are lots of books on aspiring to something. Very little are from actual people who aspired, achieved, and lost it. With each and every successful move that he made, Jim Paul, who made it to Governor of the Chicago Mercantile Exchange, was convinced that he was special, different, and exempt from the rules. Once the markets turned against his trades, he lost it all — his fortune, job, and reputation. That’s what makes this book a critical part in understanding how letting arrogance and pride get to your head is the beginning of your unraveling. Learn from stories like this instead of by your own trial and error. Think about that next time you believe you have it all figured out. (Tim Ferriss recently produced the audiobook version of this, which I recommend.)
Philosophy & Classical Wisdom
Meditations by Marcus Aurelius. I would call this the greatest book ever written. It is the definitive text on self-discipline, personal ethics, humility, self-actualization, and strength. Bill Clinton reads it every year, and so have countless other leaders, statesmen, and soldiers. It is a book written by one of the most powerful men who ever lived on the lessons that power, responsibility, and philosophy teach us. This book will make you a better person and better able to manage the success you desire.
Cyropaedia by Xenophon (a more accessible translation can be found in Xenophon’s Cyrus The Great: The Arts of Leadership and War). Xenophon, like Plato, was a student of Socrates. For whatever reason, his work is not nearly as famous, even though it is far more applicable. This book is the best biography written of Cyrus the Great, one of history’s greatest leaders and conquerors who is considered the “father of human rights.” There are so many great lessons in here and I wish more people would read it. Machiavelli learned them, as this book inspired The Prince.
Lord Chesterfield’s Letters by Lord Chesterfield. Just like Meditations, which was never intended for publication, this is a private correspondence between Lord Chesterfield and his son Philip. We should probably be happy that this guy was not our father — but we can be glad that his wisdom has been passed down. I have not marked as many pages in a book as I have in this one in quite some time. Of course, the classic in this genre of letters is Letters From A Self Made Merchant To His Son. Dating back to 1890, these are preserved letters from John “Old Gorgon” Graham, a self-made millionaire in Chicago, and his son who is coming of age and entering the family business. His letters are an incisive and edifying tutorial in entrepreneurship, responsibility, and leadership.
Plutarch’s Lives (I & II) by Plutarch. There are few books more influential and ubiquitous in Western culture than Plutarch’s histories. Aside from being the basis of much of Shakespeare, he was one of Montaigne’s favorite writers. His biographies and sketches of Pericles, Demosthenes, Themistocles, Cicero, Alexander the Great, Caesar, and Fabius are all excellent — and full of powerful anecdotes. These are moral biographies, intended to teach lessons about power, greed, honor, virtue, fate, duty, and all the important things they forget to mention in school.
The Lives of the Most Excellent Painters, Sculptors, and Architects by Giorgio Vasari. Basically a friend and peer of Michelangelo, Da Vinci, Raphael, Titian, and all the other great minds of the Renaissance, Giorgio Vasari sat down in 1550 and wrote biographical sketches of the people he knew or had influenced him. Unless you have a degree in Art History it’s unlikely that anyone pushed this book at you and that’s a shame. These great men were not just artists, they were masters of the political and social worlds they lived in. There are so many great lessons about craft and psychology within this book. The best part? It was written by someone who actually knew what he was talking about, not some art snob or critic; he was an actual artist and architect of equal stature to the people he was documenting.
The full list is at: