You are currently viewing The Greatest Orator in World History Began as a Failure. Here’s How He Changed.

The Greatest Orator in World History Began as a Failure. Here’s How He Changed.

Part I: The Fall and Rise of Demosthenes

I like stories of failure. I like to read about people who lose everything, who end up completely alone, and who are then forced to reinvent themselves from the bottom up, not because I enjoy other people’s misery, but because I would like to believe I could do the same if I had to.  

D.H. Lawrence wrote, “the brightest light throws also the darkest shadow.” When we see the great luminaries of humankind, we often forget that their successes may hide dark pasts, filled with failure and embarrassment. 

That’s why I love the story of Demosthenes. 

I don’t think I’ve ever learned of someone who started out so dejected and ended up so successful. Demosthenes is considered by many historians to be one of the greatest public speakers and politicians who ever lived. He lived during the waning golden age of Athens, the fourth century BCE, when the city was still the cradle of democracy, philosophy, science, and the arts. 

And let’s not forget rhetoric. 

In a democracy, rhetoric is a necessary skill. Without a tyrant to make all of the decisions, citizens have to persuade each other to take a course of action. In Athens, if you were a citizen, you couldn’t even hire a lawyer to give your arguments for you. You had to defend yourself in court. But there was a small loophole. You could hire someone to write your arguments for you.

That’s where someone like Demosthenes came in. He was one of these writers. In fact, he was so good at it that famous Atheneians sought him out and paid him lots of money. They knew a written argument by Demosthenes would be full of legal knowledge, wise arguments, and compelling language.   

 But here’s where the story takes its first turn. One day, Demosthenes found himself embroiled in a legal dispute of his own. At stake was his family inheritance, which consisted of a significant amount of money – millions of dollars by today’s standards. Suddenly it did not matter that he was one of the most knowledgeable citizens in Athens. It did not matter that he was a gifted writer and legal thinker, or that he was more industrious, or that he worked harder than his peers. It did not even matter that he came from a wealthy family. None of that mattered – at least, not when he had to stand and speak to the assembly himself.  

It did not go well. 

The ancient historian Plutarch writes that when Demosthenes addressed the assembly, he had a “strange and uncouth style, which was cumbered with long sentences and tortured with formal arguments to a most harsh and disagreeable excess.” It gets worse. These problems were compounded by “a weakness in his voice, a perplexed and indistinct utterance and a shortness of breath” (Plutarch 5-6). 

Demosthenes was so bad that, rather than listen to what he had to say, members of the assembly derided him. When he went back a second time to try to plead his case, they refused even to hear him! What angered Demosthenes the most was that people of lesser wisdom and experience could get full hearings, and even win cases. “Illiterate” fools and “drunken sots” he called them. The system worked for them. Why not for him? 

Humiliated and enraged, Demosthenes pulled his robe over his head and tried to skulk away from the assembly unseen. 

But here is where the story takes its second turn. In one of the great, unheralded moments in the history of rhetoric, an actor named Satyrus noticed Demosthenes sneaking off. Satyrus stopped Demosthenes and asked him what was the matter. Demosthenes vented about the injustice of his experience with the assembly. Satyrus patiently listened. 

When Demosthenes finished talking, Satyrus assured him that the skills he lacked were readily available and easy to learn. Satyrus promised that, with a few pointers, the disgraced speechwriter could transform himself into an effective speech giver (5-6). Satyrus then asked Demosthenes to repeat some lines from a famous play. Demosthenes did so – poorly. Then Satyrus repeated the same lines, only with powerful and graceful delivery. Demosthenes was amazed. I imagine that for a moment he felt he could never communicate with such eloquence. 

But then Satyrus showed Demosthenes that the difference between himself and his new pupil was not that big. It was only a matter of a few changes in “mien and gesture” and “enunciation and delivery,” and that a little exercise and practice would do the trick. Demosthenes’ confidence surged. Suddenly, the mystery of great oratory seemed to him to be “a small matter.”

He became obsessive in his practice. He built an underground study, where he could work on his newly acquired skills in private. He descended to this space daily, constantly, for months, to work on his speaking skills. Legend has it, he even shaved half of his head so he wouldn’t be tempted to go back into public until he had mastered the skills. He practiced with pebbles in his mouth to improve his enunciation and reduce his speech impediment. He recited poetry while taking long runs to improve his breathing. He gave speeches next to the crashing waves to improve his volume. In short, he worked at it. 

One of my favorite lines from Plutarch’s history of Demosthenes: “Hence it was that he was looked upon as a person of no great natural genius, but one who owed all the power and ability he had in speaking to labor and industry.” In a relatively short period of time, Demosthenes’ reputation did not merely improve; it transformed. Not only were the people willing to hear him; they frequently sought him out to speak on matters of great national importance.   

Demosthenes’ career was celebrated for the innumerable speeches he gave defending Athens against the attacks of Philip of Macdeon and Alexander the Great. Over time, he became a national hero. The people of Athens honored him with a golden crown at the height of his career. At his death, they memorialized him with a brass statue. His speech “On the Crown” is still revered as a world masterpiece. 

Part II: 5 Key Lessons from the Success of Demosthenes 

The story of Demosthenes is gripping. It’s worth reading even if you’re not trying to get anything out of it. But I am a teacher, and I cannot help but notice the crucial lessons we learn from it. Did you ever think you were pretty good at something? Then, when you actually tried it out, it turned out you were awful? Have you ever been in a situation where you think other people who are far less qualified than you have far more influence, just because they look or sound a certain way? Have you ever felt hopeless about learning a new skill or taking your professional skill set to the next level? Here are what I believe to be the five most important lessons a student can learn from the story of Demosthenes: 

  1. Embrace embarrassment, openly.

Famous failures are now a commonplace in popular media. Walt Disney was told he lacked creativity. Michael Jordan didn’t make his varsity high school basketball team. Bill Gates’ first product and company was a total disaster. Oprah was fired from her first job as a local news anchor. The list is endless. What I like to point out about these stories, as with the story of Demosthenes, is that these failures did not take place privately, without anyone’s knowledge. They were out in the open. In other words, they were not just failures; they were embarrassments. 

Most people think failure is a door closing, but it is a door opening. It sounds cliche, but researchers have become so interested in the power of failure that Columbia University recently launched a research center dedicated to studying the educational benefits of learning about and, more importantly, experiencing failure. Imagine what would have become of Demosthenes if he had not failed so miserably. He would have gone about his life as a speechwriter, making a good living quietly in the shadows of people much less intelligent and qualified than he. His life would not have been “bad,” but it would have been dull and trivial compared to what it became.

When I decided to take a public speaking workshop myself, I had already been teaching public speaking at the college level for more than a decade. I had won major awards as a college debater. I had coached speakers, given talks at conferences, and convinced myself I knew what I was doing. I had decided to take the workshop as more of a curiosity than anything else. All it took was a couple of days before I realized I was not the star I thought I was. Not even close. It was a valuable lesson, and a humbling one, which I learned out in the open, in front of many other people. If you are not prepared to fail in front of other people, you are not prepared to learn. Which leads to the second takeaway.    

  1. Embrace instruction, humbly.

The key turning point in Demosthenes’ career was not the failure itself, but that quiet moment in the street, when rather than keeping his head covered and running away from all society, he allowed Satyrus to talk to him. He allowed himself to feel the pain of his failure, and he gave himself the license to do some venting, but when he was done venting, he listened and watched. 

The way Satyrus instructed Demosthenes is a micro-masterclass in the art of teaching. First, Satyrus was no hack. He was a well known and accomplished thespian, someone Demosthenes could trust. Second, Satyrus recognized that anyone could learn this trade. He was not put off by the fact that Demosthenes was by then a notorious failure. He recognized that everyone has potential. Third, Satyrus did not beat Demosthenes over the head with lecturing. He patiently listened to Demosthenes’ frustrations and hopes; then he got Demosthenes involved in the learning process by inviting him to speak and observing his technique before offering any instruction. In other words, Satyrus did not regard the act of teaching as a one size fits all proposition. 

Additionally, Satyrus modeled the principles he taught. We’ve all heard the pejorative expression that “those who can’t do, teach.” Not so with Satyrus. He could walk the walk, so that when he demonstrated the skills he wanted to teach, it was like a revelation to Demosthenes. Finally, Satyrus broke his teaching down into easily learnable categories and skills: “mien and gesture,” “enunciation and delivery,” so that after just a few minutes, his pupil felt like the whole subject had been demystified and was ready to embrace a rigorous program of practice. Demosthenes’ transformation from hopelessness to confidence is a credit to Satyrus’ blend of empathy and clarity in his teaching. He was teaching more than 2300 years ago, and yet research today only confirms what he practiced. Empathy opens dialogue, reduces anxiety and stress, and builds trust so that students can face challenges with confidence and commitment. Which leads to the next takeaway. 

  1. Embrace practice, rigorously.

As exemplary as Satyrus was at teaching, so was Demosthenes at learning. I won’t repeat the extremes to which Demosthenes went in order to enforce his program of study. I will just point out that he did practice. I would never tell my students to shave half of their heads or put pebbles in their mouths to enforce practice. What I do require, however, is that they stop thinking about it and start doing it. Stand up. Look in a mirror. Record yourself. Do it repeatedly. Here is the best part. Public speaking is one of those skills that comes much faster than you think it will. Unlike other technical skills – and public speaking is a technical skill – the art of speaking comes naturally to us if we just give it a chance. We all already communicate every day. So, most of the work is already done. Students are often amazed at how easy it is to practice the habits. They can do it on dates, ordering meals at restaurants, talking to bank tellers, or even just standing at the bus stop. Most of us have heard the 10,000-hour principle, discussed by Malcolm Gladwell in his book Outliers. That may be what it takes to become a first-rate expert. When it comes to public speaking, if you can just become pretty good, you’ll be way ahead of most of the competition. That’s why Josh Kaufmann in his book The Personal MBA calculated a different figure: 20 hours. That’s it. 20 hours will take you from a level of total ignorance to a level of competence. As Jennifer Long points out, that’s a mere 45 minutes per day for a month. I promise you: If you were to learn the basic skills of speaking from a trained expert (see my 3-hour online course), then spend 20 hours practicing those skills, you would notice a vast difference in your competency level, and it would expand your professional opportunities in measurable ways. In future blogs, I will be exploring these skills and how to practice them. For now, it is enough to know that they can be easily learned and easily practiced.

  1. Embrace silence, judiciously. 

Despite his new-found fame, Demosthenes never forgot his roots. Even at the height of his fame and talent, Demosthenes regularly refused to speak unless he had reliable knowledge of the subject. Frequently, when he was pestered to add his thoughts to a debate, he held his tongue. His years as a speechwriter and legal thinker had taught him that any subject worth speaking about in public should be studied beforehand, “such preparation being a kind of respect to the people” (7). We do no favors for our audience if we show up unprepared and turn into blowhards. Eventually, people will find us out. Think of Stephen Hawking. He has none of the privileges associated with traditional delivery skills, but his mindful presentation style and capacious knowledge make him one of the most persuasive people in the world. Learn the skills of delivery, but do not forget: the best speakers have done their research first. This leads to the final takeaway.  

  1.  Embrace knowledge AND delivery. 

Demosthenes had learned that a showy delivery without knowledge was bad for the audience. But he had also learned that a great deal of knowledge without the ability to deliver would ensure there was no audience to begin with. The balance that needs to be struck is timeless. It was an issue in Demosthenes’ time, and it remains so today. Survey after survey and study after study show the same thing: Professionals and public leaders who actually know something AND can communicate well are in extremely high demand. Corporate executives; the U.S. Department of Labor; the Pew Research Foundation; even the Los Alamos National Laboratory – they all come to the same or very similar conclusions: technical knowledge gets you in the door, but the ability to communicate gets you to the upper floors. Quintilian, a famous Roman orator who lived a couple centuries after Demosthenes, famously reported that Demosthenes once declared the three most important elements of public speaking to be “Delivery! Delivery! Delivery!” (Quintilian 11. 3-6). 


Hopefully, the story of Demosthenes reveals the importance of overcoming fear and failure and learning good communication habits. What I also hope it reveals is that the project of learning is not that mysterious. It can be broken down into easy to understand and easy to practice skills, and that ANYONE can learn and apply them.  The Weekly Sophist will be your place to learn these skills. Stay tuned for weekly posts on what these skills are, and how you can practice them. 

And sign up for our weekly newsletter, which contains blog posts, along with the research (both ancient and recent) in grammar, logic, and rhetoric, designed for the modern professional. 


Ben Crosby is a professor of rhetoric and a communication skills consultant. He teaches courses in public speaking and presenting, argumentation and debate, technical and professional communication, persuasion and selling, and the history of rhetoric.

His work is regularly published in his field’s top academic journals and conferences. He is also the author of Presentations as Performance: A Professional’s Guide to Better Speaking.

In his free time, he spends time with his wife, Rebecca, their four kids, and their cat, Arza. He is an avid Utah Jazz fan.  

Leave a Reply