Six Old Books About How People Work

Earlier this year, I had ACL surgery. For a while, that changed how I spent both my working and non-working hours. I did a lot of my work by dictation, and because there were only so many comfortable positions I could sit in to watch television, read, or otherwise relax, I started listening to a lot of audiobooks.

I worked my way through a strange collection of very old books. I didn’t have much of a plan. I’ve always been interested in persuasion, strategy, negotiation, and human behavior, and my work has probably reinforced that curiosity. Gun.io operates across roughly 200 countries and territories, so I regularly interact with people working across very different cultures and contexts. One of the things I enjoy about that is trying to understand those differences, including the intellectual traditions and writers that emerged from different parts of the world.

That led me backward. Rather than reading only contemporary books about strategy or persuasion, I became increasingly interested in what people living in very different societies had written about the same underlying questions. The books I found most interesting were, by a considerable margin, the oldest.

The six I would recommend are The Art of War by Sun Tzu, Arthaśāstra by Kauṭilya, Rhetoric by Aristotle, The Prince by Niccolò Machiavelli, The Book of Five Rings by Miyamoto Musashi, and The Art of Worldly Wisdom by Baltasar Gracián. They aren’t really about the same thing, which is part of what makes reading them together interesting.

The Art of War

The Art of War (~5th century BC, China) is nominally a book about warfare, but relatively little of what makes it interesting requires a combative army. Sun Tzu is concerned with position, information, timing, deception, and the relative costs of different kinds of conflict. One recurring idea is that the outcome of a contest can often be determined before the overt contest begins. If you have positioned yourself correctly, gathered better information, understood the other side, and chosen the circumstances under which you will engage, the eventual confrontation becomes considerably less uncertain or risky.

I found that particularly useful because a common strategic error is accepting a contest exactly as it has been presented to you and then trying very hard to win it. Sun Tzu repeatedly invites you to ask a different question: why are you competing on these terms in the first place? Sometimes the most consequential strategic decision happens well before anyone recognizes that a contest has begun.

Arthaśāstra

Kauṭilya’s Arthaśāstra (~3rd century BC to ~3rd century CE, present-day India) is an enormous work of ancient Indian statecraft on government, economics, diplomacy, intelligence, administration, law, war, and just about everything else required to manage a state. Of all the books on this list, it probably has the widest scope, and what I found most interesting was how seriously it takes incentives.

People have interests, as do ministers, allies, adversaries, and institutions. Good intentions do not make those interests disappear. The resulting worldview can feel startlingly like modern organizational theory because it recognizes that systems work better when you understand and account for the incentives of the people operating inside them. Complex systems become fragile when they depend entirely on everyone behaving as they are theoretically supposed to behave.

You obviously should not run a modern company like an ancient Indian kingdom, and quite a lot of the book belongs firmly to the society that produced it. Still, there is something remarkable about reading a work written roughly two millennia ago and repeatedly recognizing organizational problems that remain familiar today.

Rhetoric

Aristotle’s Rhetoric (~4th century BC, Greece) comes closest to being explicitly about persuasion. Most people have encountered ethos, pathos, and logos somewhere along the way: roughly translating as the credibility of the speaker, the emotional disposition of the audience, and the argument itself. Common themes for anyone who has studied public speaking or sales. What I found more interesting was what that framework implies about communication generally.

People aren’t persuaded by propositions floating independently in space. They evaluate an argument partly based on who is making it, receive it differently depending on their existing beliefs and emotional state, and can find the same underlying idea more or less persuasive depending on how it is presented. That sounds obvious once stated, but so many people still assume that giving someone enough information should lead them to the desired conclusion.

Aristotle was thinking systematically about this problem roughly 2,300 years ago. The channels through which we communicate have changed almost beyond recognition, but the people involved remain recognizably human.

The Prince

Machiavelli’s The Prince (1532 CE, present-day Italy) has acquired a reputation that is almost larger than the book itself. It is frequently treated as a handbook for ruthlessness, but I found it more interesting as an attempt to describe political behavior without assuming that people will behave according to an idealized model of how they ought to behave.

That observation applies well outside politics. There is value in separating how a system is supposed to operate from how the people inside it actually behave. Understanding the latter does not require approving of everything you observe. It simply gives you a better description of the environment in which decisions are being made.

Machiavelli writes about reputation, loyalty, fear, incentives, fortune, competence, and the unstable relationships between leaders and the people around them. Many of his prescriptions belong firmly to Renaissance Italy, but the underlying habit of observing human behavior as it exists, rather than beginning with how we wish it existed, remains useful.

The Book of Five Rings

Miyamoto Musashi’s The Book of Five Rings (1645 CE, Japan) is perhaps the most personal of these books. Musashi was a swordsman, and the book is fundamentally about combat and mastery, but its recurring subjects are broader: timing, initiative, rhythm, perception, adaptability, discipline, and the difference between understanding a technique intellectually and being able to execute it without hesitation.

That distinction stayed with me. There are things you know intellectually, and then there are things you have practiced sufficiently that they become part of how you instinctively operate. Musashi is relentlessly interested in the latter, while also resisting rigid attachment to any particular technique. A method is useful because it works under particular circumstances, not because you have invested years in it or become emotionally attached to it.

That combination of mastery and adaptability is what makes the book interesting outside its original context. You practice until execution becomes natural, but you remain willing to abandon the technique when the situation requires something else. For a book about sword fighting written in seventeenth-century Japan, quite a lot of it travels surprisingly well.

The Art of Worldly Wisdom

Baltasar Gracián’s The Art of Worldly Wisdom (1647 CE, Spain) is difficult to describe because it consists of hundreds of short observations about judgment, reputation, restraint, timing, relationships, ambition, and dealing with other people. It is essentially a seventeenth-century manual for navigating a world populated by complicated human beings.

Gracián places enormous value on knowing when to speak and when not to, understanding how others perceive you, avoiding unnecessary conflict, maintaining independence of judgment, and recognizing that reputation has practical consequences. He is also unusually attentive to restraint. Not every thought needs to be expressed, not every disagreement needs to become a confrontation, and not every opportunity requires immediate action.

Some passages feel distinctly seventeenth-century, while others could have been written about an executive meeting last Tuesday. It is probably the book on this list that I most enjoy returning to in small doses because its structure lends itself to reading a few observations, thinking about them, and putting it back down.

Why Read Old Books?

Nassim Nicholas Taleb has popularized an idea he calls the Lindy Effect: for certain nonperishable things, survival itself provides some information about future survival. A book that has remained in circulation for hundreds of years has already survived enormous changes in technology, institutions, culture, and taste.

That doesn’t mean an old idea is correct because it is old. Plenty of ancient ideas were wrong, plenty of terrible books have survived, and plenty of excellent ideas were written recently. Age isn’t evidence of truth, but I do think it provides an interesting filter, especially when the subject is human behavior. Our technological environment changes extremely quickly, while the people using the technology seem to change much more slowly.

That was also part of what I enjoyed about the geographic range of these books. Sun Tzu wrote in ancient China, Kauṭilya’s work emerged from ancient India, Aristotle thought about persuasion in Greece, Machiavelli observed Renaissance Italy, Musashi developed his ideas in Japan, and Gracián wrote in seventeenth-century Spain. They were separated not only by centuries but by languages, institutions, religions, technologies, and assumptions about how society should be organized.

I don’t think six books can tell you what those six civilizations thought, and I would be wary of treating any individual writer as a representative of an entire culture. What they can provide is a window into how unusually perceptive people in very different places thought about problems that remain recognizable.

Maybe the thing I found most interesting when reading these books together: They don’t offer one unified theory, and I wouldn’t try to construct one from them. They are six people, writing in radically different places and periods, thinking seriously about different dimensions of human behavior. Some of their conclusions have aged badly, while others haven’t aged much at all.

But across all those differences, certain themes keep appearing. Position. Incentives. Credibility. Timing. Reputation. People have competing interests and incomplete information. They respond emotionally as well as rationally. They become irrationally attached to strategies that no longer work, misunderstand other people’s motivations, reveal things they should have kept to themselves, and occasionally enter conflicts they never needed to have or were unlikely to win.

Perhaps that shouldn’t be surprising. We have invented global communications networks, airplanes, multinational corporations, smartphones, and software that can translate between languages almost instantly. I can now work with someone on the other side of the planet under circumstances that would have been incomprehensible to every writer on this list.

The people on either side of that interaction, however, would probably be considerably more familiar to them.