6 Things Cicero Can Teach You About Writing

Cicero is believed to be the greatest speaker that ever lived. So eloquent that Caesar–often the victim of the man’s words and redresses–considered Cicero‘s achievements to be greater than his own; once remarking that it was nobler to “extend the frontiers of the mind” than it was to the “boundaries of the empire.” As I read his work over the weekend I was struck by the clarity of his teachings–that moral goodness is the only source of happiness and that can happiness prevail even as you’re being drawn and quartered. From that I jotted down his principles for becoming the perfect speaker from his discussion “On the Orator” and translated them into the principles for becoming the perfect writer. You can take the passion and eloquence that carried him from humble origins to two millenniums of posterity and tweak them to apply them to your writing. So here are 6 (of the many) Things that Cicero Can Teach You About Writing and hopefully, life too:


Master the Subject: All of It

There is no way around this. He writes that unless a speaker truly “grasps and understands what he is talking about, his speech will be worthless.” That is clever word play or eloquence never trumps the material. In Rome the finest speakers were at an age that today we consider elderly–because they’d spent a lifetime acquiring knowledge. Cicero likens the study of a subject to a lawyer taking on a case for a client. They must know everything. They must be acutely aware of the nuances of the material, the theory and its precedents. Vincent Bugliosi as he tried Charlie Manson would approach witnesses with literally dozens of legal pads filled with questions. And he did the interrogations himself so he could absorb not just the victim’s words but their feelings, emotions and tone.

This is what separates a rhetorician from an orator according to Cicero. The former knows language and the latter knows the truth. It is what separates a newspaper reporter who plugs quotes into the story format and the author who has dedicated years to the material at hand. And I think you need to ask yourself, who do we remember and who do we respect? The transient compilation of information of a text book or the holistic study of a book like Moneyball or Liar’s Poker that makes you feel like you lived it?

Understand Human Nature: Psychological Warfare

It’s very easy to think that knowledge of the details of the discussion at hand is enough. They are not. Cicero wrote that the speaker will never find the right words without a “thorough understanding of human nature and psychology.” Through that alone can they derive what is appropriate and most effective for the audience. Not to mention, their opinions lack a foundation of reality if they are not solidly based on the human tendencies and beliefs. People respond to symbols, alliteration, and allusions. You know this, use them. We’re self-interested–appeal to it. We’re proud–capitalize on it.

If his first rule was details, this is the philosophy. You must know the canon.You can’t debate politics without The Republic or military affairs without Von Clausewitz and an intricate study of history. Or discuss love and romance without poetry, observance and first hand-experience. You can’t advocate policy or gives advice unless you’ve sat down and truly watched people–not as you’d like them to be but as they are. Writing is the same way. Your characters feel like cardboard if they were created shut up in your house or your wisdom falls flat without an understanding of what people want to hear about. For this reason the books of most professor’s fail to sell: the writer spent all their time teaching about life instead of living it.

Focus on What Matters: Be Concrete

Cicero said that the difference between a philosopher and an orator is that a philosopher speaks generally in empty classrooms while an orator debates matters of national importance on the floor of the Senate. A writer of value, according Cicero, would be someone who takes the broad strokes of the thinker and translates them into the specific, applicable language of the doer. Without concreteness we have audible masturbation–onanism. What we need is someone who combines theory with practicality and a laser-focus on the stuff that matters. How else, he says, are you qualified to attack the actions of a general without knowledge of military theory? And conversely, what good is that theory if you cannot tie it to his actions?

Use Fear: Be Human to Reach Humans

Shamelessness is the fastest way to alienate your audience. So even if you feel no fear in front of a crowd, Cicero thinks you ought to at least keep up the pretense–to show that you are human. He claims that Crassus, another great speaker, feigned diffidence each time he approached the podium so he could connect with the audience instead being foreign or above them. Writers who show no shame, he said will be “rebuked” and “heavily penalized” by the reader. So that garbage about seeing the audience naked to calm your nerves is all wrong–you have the nerves for a reason, acknowledge them, embrace them even. If you’re unsure of something, admit it and make it an asset instead of a weak spot in your message. This is the psychology that Cicero knew you needed to master.

Enthusiasm: Passion

The only way to navigate the difficulties of the other obstacles is to actually love what you do. That means, you’d do it for free or if no one was reading. He said “You need just one thing: enthusiasm–a passion little short of love.” If you don’t have that, why bother? People certainly aren’t going to want to read what you could barely drag yourself to write. That means working hard, like Demosthenes who would fill his mouth with pebbles and recite verses to strengthen his tongue, who through practice alone broke himself of a stutter. A lot of writers don’t have this and it shows; they write about what they think you want instead of what they care about. And that is just sad.

Ask the Experts: Learn from Others

It is the writer’s job to know a lot but not everything. So when you don’t know, consult the people who do. And with your ability to translate, amplify and support, he said, you ought to be able to make a more powerful argument on the subject then even they are able to. Often the “experts” have spent all their time on the first rule and none on the second, making it opportune for you to navigate a merger. Cicero listed the people he knew who he would turn to when he needed help or advice on a subject outside his expertise. Like him, you should try and cultivate these relationships and have them On Demand. If the Forum was the battlefield he said it was, then this is your armory, a stockade of knowledge for when you need it. Marcus Aurelius said that like a “soldier storming a wall,” when you find trouble, it’s perfectly fine to have a “comrade to pull you up.”

Do the Opposite: Speak to Write Better

Cicero felt that the best way for a speaker to attain eloquence was to write extensively–that practice in the more meticulous and thought-out medium would help in extemporaneous discussions. In writing, the converse is true. Getting better at speaking, developing the ability for words to roll off your tongue will translate into a more fluid prose. As you raise your threshold on the state or at the podium, you ought to see your writing improve as well. He also recommends (as do I) to re-write (speak) the great works that have come before you. As you transition to original creation you can take that momentum with you. It’s like getting a massive head start. In fact, it was in translating classic Greek to Latin that Cicero invented and gifted us the words “quality” “individual” “vacuum” “infinity” “moral” “notion” and “comprehension.”


Just as Sun Tzu said that if you know yourself and the enemy you will win every time, if you know the material and people you will do the same. If you are concrete, work hard and rely on experts for specialized knowledge, that victory will be a landslide. Cicero could put down rebellions with impassioned speeches, so surely you can convince the reader of the merits of your arguments with the same tactics. Unfortunately, these are not the lessons taught in school–we learned to write on things we didn’t know much about, were told to divorce ourselves from how people normally think, to be theoretical and quote only from certain sources. That’s not what I want to get in the habit of doing. And I absolutely hate it when I can tell that other writers are. We’ll probably never be as eloquent as Cicero (at least I won’t) but even if you make it halfway, you’ll be clearer, more inspiring and have more passion.

If you liked this, then try this: On the Spartans and the Perfect Paper

Source: On the Good Life is the collection of Cicero’s essays that I used for this post. The translation is excellent. You should buy this book.

Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.