Archives For October 2007

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.

There is this town next to the one I grew up in called Orangevale. It’s come to symbolize everything I don’t want my life to lead up to. I remember as a kid just getting this choking feeling in my throat whenever I would visit friends there. I remember realizing “I’d rather put a gun in my mouth than end up living here.”

Not because it was poor–it wasn’t–but because it was just sad. You could just feel the toll that getting up everyday and working 40 hours a week as mediocre insurance salesman or secretary took on people. I drove through it a while back and from the cocoon of my car remember hearing those piercing screams of desperation rattling off chain link fences and dry, brown lawns. People just waiting for the weekend so they can sit and eat dinner on tv trays or yell at their kids. Alinsky called this “living in illusions of partial escape.”

I still feel that choking–that fear. I just cannot end up there. To work your whole life at the governmentally mandated limit for what? At something you’re ok at but would quit if you could get a few more dollars doing something else, for what? To have the white picket fence that needs so desperately to be repaired but you just don’t care enough to do it, for what? To be so angry, and confused, and wonder why your kids act out in violence, for what?

And for some reason, kids I went to college with are just counting the days before they graduate and move back. No wonder it’s all about indulgence, artifice, delusion and those “if I don’t travel abroad now, I’ll never get to do it again” trips they have the state pay for. It’s a last gasp before they voluntarily go under. Worse, most of my friends never even left.

That’s not me. I won’t let it be. I’d rather be dirt-fucking-poor and doing exactly what I want then take the sucker’s payoff of that life. Or, better yet, have both–the money that comes with rarity and value and the passion of a life of meaning. But you’ll hear a lot of excuses for why that’s not possible or not worth it or too hard–ask yourself, as I try to, “according to who?” And then you’ll see them as the tinny, self-serving rationalizations from people scared to death of life and effort that they are.

“Can I get a cup of water?”

“We don’t have water here.”

I was at a Pinkberry in LA earlier in the week overpaying for desert and I got thirsty and assumed they’d give me a drink for free. But they didn’t. And I guess I should have gotten mad–it’s pretty awful customer service–but I couldn’t. I respect the balls that that took. Somewhere along the line, someone made the conscious choice not to serve water. IKEA did it too. Someone said “Why do we pay to give everyone bags that they just throw away when they get home?” and they stopped doing it.

You can see countless examples of industries that have decided to die with whatever practices they were born with. The album, regardless of whatever musicians cry, is not a collective artistic statement. It’s just a packaging device designed to deal with fixed costs. Otherwise, iTunes would show that songs in “classic” albums were downloaded equally. Nope, 3 or 4 songs are almost always significantly more popular than others while others are almost actively disliked. But bands keep cranking out albums even though they could sell the songs online as they make them. Why isn’t the mail delivered on Sunday? Why do the newspapers still publish stock tables? Why do cars still have cigarette lighters instead of electrical outlets? And why does the penny even exist anymore?

Because no one has bothered to stop and questioned “the way things have always been.”

The United States Constitution of the isn’t a suicide-pact. Should anything else be? Things are changing at a phenomenal rate of speed. You cannot get in the habit of traditional or emulative thinking. If the data doesn’t support your position, you’re probably being generous when you call it a position. Business have at least some excuse: Bureaucracy. What excuse do we [people] have?