The Classics: The Original Twenty-Five

What is a classic? Here’s Thomas Cleary’s definition:

“On a small scale, a classic yields significantly different meanings when read in different circumstances and moods; on a large scale, a classic conveys wholly different worlds when read in different times of life, at different stages of experience, feeling and understanding of life. Classics may be interesting and even entertaining, but people always find they are not like books used for diversion, which give up all of their content at once; the classics seem to grow wiser as we grow wiser, more useful the more we use them.”

It is no secret to those around me that I enjoy reading, both for the joy and for the practical utility it has yielded me. Below is a selection of books that I deem to be my own classics. I read them in my early twenties and was profoundly influenced by all of them.

As I grow older, they continue to enter my thoughts and shape my actions, I hope that amongst this selection you can find something equally life-altering.


1. Meditations by Marcus Aurelius

Marcus—perhaps the only true philosopher king—had unimaginable responsibility and carried the Roman Empire on his shoulders. Stoicism, as Marcus presents it, is not a stuffy academic philosophy. It is a philosophy for pragmatists. A philosophy which provides armour for the active man against the assaults of life. Thanks to the Meditations, we have access to Marcus’ playbook for handling people, misfortune, death and struggle. It teaches us, as philosophy should, how to live.

2. Letters from a Stoic by Seneca

Another of the great Stoics was Lucius Annaeus Seneca. A man with near-limitless wealth, he was what Nassim Taleb calls an aggressive stoic; he enjoyed all the benefits of success, whilst teaching himself to be impervious to losing it all. Despite this wealth and success (or because of it) Seneca was cast as the tutor to the tyrannical Nero, was banished from Rome in his later life, and was later ordered to take his own life by the same Emperor he once tutored. In his letters to Lucilius, Seneca offers sound advice on dealing with success, confronting grief, learning from others and the true meaning of friendship.

3. Discourses and Selected Writings by Epictetus

Captured in the form of lecture notes by his student Arrian, Epictetus gives a more thorough treatment of the logic of Stoicism. A key theme in all of these lectures is the dichotomy of control. The separation of events into what we can control and what is not in our power to control. He advocates, along with Marcus, limiting good and bad solely to your own actions and thoughts, whilst building an indifference to everything else.

4. Man’s Search for Meaning by Viktor Frankl

Viktor Frankl’s portrayal of his experiences in the concentration camps of World War II is one of the most empowering and sorrowful things you will ever read. Frankl shows us that even under the most degenerate of authority, in the lowliest of conditions, we always have a choice of how to act. Always.

But as we grow older and our culture moves on, the danger of losing touch with the realities and impact of the World Wars becomes more apparent. Books like Man’s Search for Meaning are an invaluable tool to help us re-forge this connection and to remind us of our all too human past.

5. The Complete Essays by Michel de Montaigne

When I think of Montaigne, I think of joy. Of a life lived with gaiety, with vigour, with unquenchable energy. He was an unabashed sceptic, completely aware of his own fallibility, comfortable saying I don’t know. He was a student of the human psyche in conflict and in conduct. His essays radiate and infect you with a desire to question, to explore, to play. They encourage you to exceed your capacities and to open your eyes to the wonders of the people and the environment you live amongst.

6. The Open Society and its Enemies by Karl Popper

Popper’s work is a perfect model of an attitude which is in dire need in the age of experts and gurus. Irreverence. Popper takes on some philosophical giants (Plato and Marx). And he finds them wanting. When he said that “we must break with the habit of deference to great men,” they were not empty words. Popper shows us how with this demonstration of incisive thought, clear communication and his defence of democracy.

7. Antifragile: Things that Gain from Disorder by Nassim Taleb

Nassim’s work changed my mind. I had never considered our response and approach to comfort, order, routine and certainty. I had never thought about what happens when we deprive ourselves of their opposites: variety, volatility, stress, uncertainty. Of all the things I took from Taleb’s Incerto—and there is a lot—it is this shift in mindset and philosophy that has impacted my life the most. The notion of turning into disorder and uncertainty. Embracing it rather than shunning it. Capturing it in my every day life. Learning to love volatility not hate it. This has been the lesson I am most grateful to Nassim for. My quest to become a person that gains from disorder is only starting, but it has already enriched my life.

8. The 48 Laws of Power by Robert Greene

The central idea behind this book is an understanding of the mechanisms of power, influence and social environments. Some cite the malice and immorality of power as their chief reason for avoiding such unashamedly practical texts. But it is for precisely this reason that we must look at the underbelly of human nature. By recognising the structures and strategies of power, we can protect ourselves against those who abuse it, and advance our own interests, whilst eliminating collateral damage to others. As Publius Syrus puts it, “He can best avoid a snare who knows how to set one.”

9. Mastery by Robert Greene

The depth that Greene penetrates into the learning process is such that when you revisit your own work or craft, you see it in a new light. He breaks the learning process down into the following stages: finding your life’s task, completing an apprenticeship, experimenting in the creative-active phase, and assimilating your skills to achieve Mastery.

Of more importance than this breakdown is the formula that Greene observes. Mastery = time x intense focus x self-belief. It seems simple, but once you start to examine it, you begin to see how often we expect mastery from ourselves and others, whilst neglecting one or more of the components. We expect it overnight. We think it can be gained in an hour every day. We mistake our lack of confidence for the presence of humility. Greene neutralises those false conceptions to reveal the time, dedication and sacrifice necessary to attain the highest heights. Mastery is a powerful text. The mastery formula is even more powerful. Apply it.

10. Rules for Radicals by Saul Alinsky

Saul Alinsky was a doer in every sense of the word. His reputation as a hell-raiser is built not on myth, but tangible deeds. Rules for Radicals, completed shortly before Alinsky passed, is the compendium of his experiences organising, motivating, directing and harnessing the power of the people. A man who saw reality as it was, not as he wished it to be, he leveraged the system to his fullest advantage to bring about change. A champion of effective action who we have much to learn from.

11. Strategy by B.H. Liddell Hart

The indirect approach is a game changer. The process of upsetting equilibrium (Hart calls it “dislocating”) before striking, and proceeding to exploit it, seems intuitive now, but in practice is often overlooked. The indirect approach is revealed in the context of war, but it is useful in application to anything that requires strategy. You also learn about the strategy spectrum, the difference and interplay between tactics, strategy and grand strategy, along with Hart’s nine prescriptive aphorisms for effective strategy. A book for anyone who has to make plans, develop a course of action, and implement it in the most effective way.

12. Brave New War by John Robb

The era of state versus state warfare, of conflicts like the World Wars has passed says John Robb. The new warfare is one that utilises what Robb calls systems disruption. Hailing from Lawrence of Arabia and his methods in the First World War, the new style of conflict is one that targets infrastructure instead of casualties, and uses technological advances to exert millions of pounds of economic damages for a trivial cost. An enlightening and scary look at the effects of global interconnection and the dangers it poses.

13. The Art of War by Sun Tzu

The classic manual of conflict. Thomas Cleary’s translation makes this text accessible and displays how relevant it still is. It is no coincidence that the work of great strategists like Liddell Hart, Robert Greene, John Robb, John Boyd, Alinsky and many others all end up at the same principles espoused by Sun Tzu over two millenia ago. The emphasis on fluidity, on adaptation, on timing, and on the importance of winning without fighting, is something we must periodically remind ourselves of.

14. Thinking, Fast and Slow by Daniel Kahnemann & Amos Tversky

The culmination of forty plus years researching, testing, evaluating and solidifying his concepts, this practical guide is the tool to help you make critical decisions, whilst avoiding our innate psychological biases and flaws. But be warned, once you start to dig into the literature behind biases, you will disappear for a long time. I also advise reading the work of Gerd Gigerenzer. He sees some of the same problems and issues with our judgement and understanding of risk, but opposes how Kahneman et al. recommend solving them.

15. Quiet by Susan Cain

Most pop psychology books draw on already over-used and ineffective insights and offer little in the way of practical strategies. Not this one. Quiet is a great medicine for a cultural outlook that favours the brash, the loud and the over-confident. Possibly the biggest perception here is that while extroverts recharge and recuperate around people, introverts need to regain their energy in less stimulating environments.

16. A Few Lessons from Sherlock Holmes by Peter Bevelin

Piecing together the principles and methods that make Sherlock Holmes such an incisive reasoner, this short volume will alter how you look at your own thinking and judgement. Better approached as a collection of statements and aphorisms, rather than a free-flowing narrative, Bevelin simultaneously gives you the tools to be a better thinker, and makes you want to read the Sherlock Holmes stories. This short text is a prime example of the power of deductive reasoning.

17. Never Let Go by Dan John

This book is mostly about lifting and training. But some of the parallels between lifting and life are so blatant that they are unmissable. Discipline, support systems, a healthy social environment, honest and regular assessment – all are paramount. This book also taught me about elegance, grace in performance and infected me with a love of lifting and learning. Dan’s later books Intervention and Can You Go? are more industry-specific, but deal with a worldwide problem; how to make sustainable behavioural change and promote a lifetime of improvement.

18. Musashi: An Epic Novel of the Samurai Era by Eiji Yoshikawa

Takezo starts out as an unruly and typical young male, salivating at the spoils and glory associated with war. He knows defeat and exclusion and is reborn after a period of intense seclusion and study, as Miyamoto Musashi. Actively seeking the Way, he meets cunning enemies, subversive associates and constant opposition. A man at odds with the conventional way of doing things, by necessity, he has to be unconventional, in both his ongoing education and his tactics. By seeking out the major schools of the samurai art and challenging them, he observes their weaknesses, absorbs their strengths and synthesises his new experience with his own skills and knowledge.

Musashi is the perfect example of the wanderer who, by examining all of the extremes and peculiarities of his discipline, proceeds to surpass them. He studies form to leave form. Musashi emphasises the humility and the constant re-mastery that is necessary to become the best. It’s a tale of the twisting path to utter perfection.

19. Zorba the Greek by Nikos Kazantzakis

Life is defined by contrasts, as is this tale. A young English writer setting off to Crete encounters Alexis Zorba. The Englishman is the stereotypical intellectual-philosophiser, pondering and questioning his every action, careful at every junction and paralysed by his rationalising. Zorba stands as a free spirit. He follows his passions. He loves with all his heart and lives with all his energy. Depending on your perception, this can serve as a cautionary tale to reduce the heartache caused by Zorba’s impulsive instincts, or as a call to embrace the reality of your surroundings, and enter into every action with vigour.

20. The Godfather by Mario Puzo

As well as being a complete page turner, Puzo’s tale depicts the influences of power, loyalty and anger upon a family. Tucker Max called it “a guide to modern manhood.” There are lessons in subtlety, strategy, reputation and recognition. And this: the Don “claimed that there was no greater natural advantage in life than having an enemy overestimate your faults, unless it was to have a friend underestimate your virtues.” Read that a few more times.

21. The Collected Works of Kahlil Gibran

Gibran’s ability to capture and evoke unspoken emotions is still one that strikes me every time I come back to his work. After being asked to give a reading at my friend’s wedding, I immediately chose On Marriage and On Children. Another of his poems, The Scholar and the Poet, is one that I find myself coming back to. Whilst The Prophet is the most well-known of his works, his collection of aphorisms in Sand and Foam, along with some of the parables in The Madman and The Forerunner, are equally striking. Joy, sorrow, friendship, love and work are all touched upon.

22. 12 Years a Slave by Solomon Northrup

A testament to the sheer savagery of human beings that can be awakened by an overwhelmingly cruel culture and upbringing. It details atrocities that, with our current cultural mindset, seem unimaginable. We view it as impossible that one man could treat another in such ways. It is not. And the reason may be that the slaves weren’t considered as humans. They were perceived to be animals. Uneducated. Worthless. A mere possession.

While this account highlights the cruelty of man, it is, perhaps more importantly, an ode to the indomitable spirit of an individual who has vowed to keep going, fight back and reverse the injustice so prevalent around him. ​

23. Autobiography of Malcolm X by Malcolm X and Alex Haley

Malcolm X’s descent into a life of poverty and crime, into robbery and a skittish, paranoid existence eventually lands him behind bars. Through a rigorous re-education, a total reinvention of self, he comes out the other side as a leading catalyst in the civil rights movement. Refusing to be censored. Refusing to silenced. Refusing to be caged in. He fought for what he believed in and paid for the struggle with his life.

We often think that our circumstances paralyse us, making it impossible for us to move on or change. Malcolm shows us that if you have the audacity to change your mind and follow through, your circumstances are a non-issue.

24. Ender’s Game by Scott Orson Card

This is a raw and insightful tale of what it feels like to be thrown into an alien environment with no friends, little direction and no respect. And for that reason, if you’re starting out in a new job or a new environment, I highly recommend it. Ender, after being bullied and targeted, realises that he must attain two things to survive. He must gain the respect of his peers, and that respect must be based upon his capabilities, his excellence. He has to become really fucking good.

The way he does this will be familiar to anyone who understands the process of learning. He studies his environment – who matters, what makes people act and react, who has the influence. He studies his peers – his enemies, his instructors, his teammates. And he studies himself – his weaknesses, his talents, his knowledge. By acknowledging no authority except excellence, and endeavouring to become so good they couldn’t ignore him, Ender not only survives, he thrives.

25. Master of the Senate: The Years of LBJ III by Robert Caro

Learning and education is not just about ideas, conceptual models and abstract frameworks. It is about an understanding of human nature, an understanding of men. I’ve read no better demonstration of just how to go about attaining this understanding than Caro’s books. LBJ arrives in the Senate and watches. He observes. He pays close attention to the relationships between Senators, to who has stature and power. He reads men, determines what makes each individual tick, what makes each person vulnerable and how he can use that to his advantage.

Yes, LBJ was ruthless and amoral. Yes he used the men around him as instruments of his ambition and desires. But just because you don’t condone his methods, doesn’t mean you can’t learn from them. LBJ was one of the keenest observers of men, social pressures and power. Whether we like it or not, these are forces that are still prominent in our own environment. There is a reason that Robert Greene called this series the greatest self-help books he’d ever read.


 A Final Note On Reading

“To this day I still have the instinct that the treasure, what one needs to know for a profession, is necessarily what lies outside the corpus, as far away from the centre as possible. But there is something central in following one’s own direction in the selection of readings: what I was given to study in school I have forgotten; what I decided to read on my own I still remember.”

Nassim Nicholas Taleb, Antifragile