7 Lessons From Diogenes That Will Change The Way You Look At Life

Learn from the notorious philosopher-troll.

Alvin Ang
Alvin Ang
Mar 3 · 12 min read
Bronze sculpture of Alexander the Great and Diogenes. Source: Wikipedia Commons

Diogenes was one of the most controversial philosophers of all time. Here he is pictured above on the left, telling Alexander the Great to politely screw himself.

The man who would become one of the founding fathers of Cynic philosophy was exiled from his hometown of Sinope for debasing the currency. At a loss at what to do next, Diogenes consulted the Oracle, who told him that he should — wait for it, proceed to debase the currency in none other than Athens.

Wisely taking this to mean political rather than financial debasement, Diogenes became a vocal critic of many cultural conventions of the city, speaking out against hypocrisy and moral corruption.

Diogenes believed that there is great virtue in a simple life of poverty and that this virtue is better extolled in action than in theory. He went to extreme lengths to exemplify his ideals and became notorious for his philosophical stunts. Some of them include:

  • Living in a jar in the Athenian marketplace
  • Eating, defecating and masturbating freely in public
  • Crashing Aristotle’s lectures with a plucked chicken
  • Carrying around a lamp in the day, telling curious onlookers that he was just looking for an honest man
  • Rebuffing Alexander the Great (more on that later)

These antics prompted Plato to call him “Socrates gone mad” — which is quite possibly the best-backhanded compliment I’ve ever read. In this article, we’ll take a look at seven lessons gleaned from the life and larks of Diogenes the philosopher troll.

These lessons will, at the very least, give you a chuckle; but if fully absorbed, will help open your eyes to a different, less serious way of living.

Let us begin!

Painting: Jean-Léon Gérôme, Diogenes of Sinope, 1860. Source: Creative Commons

Possessions Do Not Maketh Man

Diogenes only possessions were his jar, some rags for clothes, and a bowl. However, when he saw another beggar drink from his cupped hands, Diogenes exclaimed, “I have been a fool, burdened all these years by the weight of a bowl when a perfectly good vessel lay at the end of my wrist.”

He proceeded to smash his bowl to smithereens, reducing his count of possessions from three to two. As you can see from the story above, Diogenes couldn’t care less about worldly possessions. He thought that,

“It is the privilege of the gods to want nothing, and of godlike men to want little.”

This idea is echoed by Epicurus, the premier philosophy of pleasure, who taught that “It is better for you to be free of fear lying upon a pallet than to have a golden couch and a rich table and be full of trouble…Not what we have, but what we enjoy, constitutes our abundance.”

This level of abandonment may seem extreme, but keep in mind that many great spiritual figures also preach the renouncement of worldly belongings. They range from the likes of Buddha to Gandhi to Christ himself, who told a wealthy man, “If you want to be perfect, go, sell your possessions and give to the poor, and you will have treasure in heaven.”

I’m not saying that the only way to live a virtuous life is to live the life of a wandering ascetic. I’m saying that worldly possessions aren’t as important as we give them credit for.

Keep in mind that it doesn’t matter if you’re an undefeated conqueror or a poor beggar, you enter this world empty-handed, and it is with empty hands you will depart.

It is not what we own, but what we love, that defines us.

You Don’t Have To Own What Gives You Joy

Continuing the thought of eschewing possessions, Diogenes said,

“What I like to drink most is wine that belongs to others.”

This little tongue-in-cheek quote reminds me of a saying from Kevin Kelly: “Friends are better than money. Almost anything money can do, friends can do better. In so many ways a friend with a boat is better than owning a boat.

I’m not saying that you should be a parasite forever living with your family and leeching off your friends. I’m saying that possession does not necessarily constitute enjoyment. Here are some examples:

  • You don’t have to own the skyscraper you’re standing on to enjoy the great view it affords
  • Renting an apartment instead of owning it frees you from the stress of maintenance and upkeep
  • Renting a suit for a grand one-off occasion instead of buying it will not only save you money but also save you from the hassle of tailoring, ironing and dry-cleaning
  • Hiring an Uber instead of owning a car means you can enjoy being driven around without the worry of car payments, damage, ticketing, oil prices and a little something known as staying awake while you drive so you don’t die
  • Playing with a dog owned by a close friend or family member means you get all the love and affection sans the vet trips and poop scooping
  • And more

Granted, I’m exaggerating a little. I myself would like to own a nice house and maybe a dog or three someday. But the fact remains, it is not the things we own that make us happy, it is the experience that comes with things that do.

This is a fine but important distinction to make.

Too many times, the things we own end up owning us. The next time you find yourself wanting to impulse purchase something thinking it’ll bring you joy, ask yourself, “Is there some other way to experience the feelings the object in question will give me without actually buying it?” If the answer is yes, refrain.

This is how you live a fuller life with less.

“Alexander and Diogenes” Painting by Gaspare Dizian (1689–1787) Source: Creative Commons

Don’t Cow To Great Men

Alexander the Great, the greatest conqueror the ancient world has ever seen, was travelling through Corinth when he had a hankering to visit Diogenes, a philosopher whom he had long admired from afar.

Upon arriving at the philosopher’s home-jar, the young king found the old philosopher sleeping. It is said that Alexander, who was a lifelong fan of the Illiad, then borrowed a line from Homer, saying, “To sleep the whole night through ill befits a man of counsel.” Diogenes, awakening, countered by quoting the very next line, “Who has people to watch over and a multitude of cares.”

Alexander was impressed, and asked Diogenes if there was anything he could do for him, promising to grant any boon he might desire. Diogenes then famously replied:

“Yes, move a little to the side; you are blocking the sun.”

Alexander’s companions bristled at this, but Alexander’s esteem of the philosopher only deepened. He laughed and said, “If I were not Alexander, I would wish to be Diogenes!” Diogenes, ever cunningly cutting, replied, “If I were not Diogenes, I too would wish to be Diogenes.” Instead of punishing the philosopher, Alexander left an even bigger fanboy than he came.

So many of us think that might makes right. Of course, it is normal, even prudent, to want to get on the good side of those with more power and clout than us. But this does not mean that you should be a pale willow bending in the wind.

Diogenes was faced with a choice when Alexander granted him a boon: Accept one from the Macedonian king, and leave the encounter safe and enrichened, or stick to his ideals and risk offending he who is the most powerful man in Greece. Diogenes chose the latter.

Don’t seek needless confrontation, but when your Alexander shows up at your doorstep with an army by his side and temptation on his lips, know that this is one of the rare times in life where you only have two choices.

You can tell him what he wants to hear and thereby betray your ideals — or you can be brave; brave through actions such as not giving up your seat, refusing to salute Hitler and asking Alexander to get out of your sun, a choice that Rosa Parks, August Landmesser and Diogenes the Cynic made, all those years ago.

You may think that I’m making a big deal out of nothing, but a quick glance at history will tell you that unspeakable atrocities are rarely committed by a single despot. They are instead usually carried out by ordinary men and women just following orders.

It takes real strength of character to speak your truth when confronted with immense power. But as the saying goes, all it takes for evil to triumph is for good men to do nothing.

Remember, might doesn’t make right. Right makes right.

The World Is One

Diogenes was the first person to use the word “cosmopolitan”, calling himself a citizen of the world.

This was a revolutionary idea back in the day. There were no smartphones, no round-world flights, no globalisation. Greece was still a bunch of squabbling city-states ever at war. To describe yourself as having no affiliation to your country is to risk being labelled a traitor, an executable offence.

But Diogenes, as he did throughout his life, stuck to his guns. It was only after his death that the rest of the world caught on, coming to the slow-dawning realisation that every individual belongs to two communities; the local community of one’s birth, and to a larger extent the wider community of the human race to which we all belong.

The idea that we ought to share the same rights was revolutionary. It gave rise to movements as impactful and diverse as the introduction of human rights, women empowerment and the battle against racism; all the things we believe in and take for granted now.

And it was good old Diogenes, the so-called madman, who called it first.

You Don’t Have To Do Things You Despise If You Live A Simple Life

“A philosopher named Aristippus, who had quite willingly sucked up to Dionysus and won himself a spot at his court, saw Diogenes cooking lentils for a meal. “If you would only learn to compliment Dionysus, you wouldn’t have to live on lentils.”

Diogenes replied, “But if you would only learn to live on lentils, you wouldn’t have to flatter Dionysus.”

This is something that resonates deeply with me.

Despite having starred in The Apprentice, I have never once held a corporate job. Much of that has to do with the bad experience I had in the Army. There I, for the first time, encountered toadies sucking up to their superiors for benefits. It left a bad taste in my mouth.

Obviously, not every worker is a sycophant. Yet so many of us do things we innately despise in order to get ahead. To get money, fame, to get a higher position on the social ladder of life. The unspoken consensus seems to be the faint hope that there will come a time where we will finally have enough to feel satisfied.

But here’s the thing: Enough is an imaginary construct that varies from person to person. What will bring tears of joy to a humble labourer will barely register in the eyes of a king. Happiness can be an ever-moving goalpost. This is a concept known as the hedonic treadmill.

Thus, to engage blindly in the rat race is to be a rodent forever on the wheel, trapped in a loop of your own construction. The only way to escape this rut is to do the opposite of what everyone else is doing; instead of lusting after more, seek to minimise your desires instead. Like Epicurus said,

“Do not spoil what you have by desiring what you have not; remember that what you now have was once among the things you only hoped for…

Nothing is enough to the man for whom enough is too little.”

Think about it; do you really need a million-dollar watch, an Armani shirt or a cherry red Ferrari to be happy? Or are you seeking validation through accomplishment, contentment through spending, your 15-minutes of fame through your flashy exploits? If so, take care, for no amount of luxury can fill the abyss of a greedy human heart.

Far better for you to find out what really makes you, and you alone, happy, then focus on that. Ruthlessly cut out all unnecessary distractions and expenditures.

This is how you live a life full of things you love instead of deeds you despise.

“Diogenes Searching for an Honest Man.” Paniting by J. H. W. Tischbein (1780). Source: Wikipedia Commons

Speak Your Truth — Even If It Means Going Against The Crowd

“A report that Philip II (Alexander’s father) was marching on the town had thrown all Corinth into a bustle; one was furbishing his arms, another wheeling stones, a third patching the wall, a fourth strengthening a battlement, every one making himself useful somehow or other. Diogenes having nothing to do — of course, no one thought of giving him a job — was moved by the sight to gather up his philosopher’s cloak and begin rolling his tub-dwelling energetically up and down the Craneum; an acquaintance asked, and got, the explanation: “I do not want to be thought the only idler in such a busy multitude; I am rolling my tub to be like the rest.”

Diogenes’s unconventional ways meant many dismissed him as a madman. To this he replies,

“It is not that I am mad, it is only that my head (thinking) is different from yours…

Of what use is a philosopher who doesn’t hurt anyone’s feelings?”

Too many times, we opt to go with the flow because we are afraid of offending others, of standing out, of making ourselves a target. But as the saying goes, “There is only one way to avoid criticism, and that is to do nothing, say nothing, and be nothing.”

The surest way to find critics is to do things differently. After all, the most heinous sin a crab in a bucket can commit is to make a run for the rim. His fellow crabs will be the first to tear him down, thus keeping him — and all of them, stuck and very much doomed.

This is not to say that you should be a pariah for the sake of it. This is to say that if there is one thing you truly believe in that others don’t, then you owe it to yourself — and to whoever your ideals will help, to defy the crowd.

Remember, many conventions that we take for granted now were unpopular back in the day. Not too long ago, slavery was widespread and accepted. The Wright Brothers were laughed at when they tried to build planes. The same thing happened to Louis Pasteur when he posited that diseases were caused by invisible entities called “germs.”

Abolition, aeroplanes and antibiotics; these things didn’t happen by themselves. They took men with the courage to defy the mockery of the crowd to bring into reality. So seek to be among the company of these lonesome stalwarts.

For it is the man brave enough to defy the mockery of the crowd who serve to propel the human race ever forward.

Embody Your Ideals

This last point, to me, is what makes Diogenes stand out among his contemporaries, and is likely the very reason why he is still remembered with reverence today, more than two thousand years after his passing.

Diogenes didn’t just speak his truth — he embodied it. Living in a jar, begging for scraps and telling conquerors off; these feats couldn’t have been easy or comfortable. Yet Diogenes did it anyway because it was what he believed in.

We can preach ideals, sing hymns and talk theory until the cows come home, but to quote Benjamin Franklin, “Well done is better than well said.” Many will boast, praise and promise, but when trouble shows up at your doorstep and the time comes to put up or shut up, the sad truth is that very few will live up to their words.

Be among the few.

The world doesn’t need any more preachers, speakers, priests and influencers. What we need are doers. What we need are less weak willows swaying in the wind and more strong oaks who stand against it, deep-rooted and everlasting, faithful like hound-like Diogenes. What we need are strong men who are willing to exemplify their ideals until the very end.

So live your truth. Don’t just speak it.

That is how you earn the respect of commoner and kings alike. That is how you change the world; not one word at a time, but one deed at a time. And above all, that is how you best remember the teachings of Diogenes the Cynic, long-dead, but due to the exemplification of his ideals, never forgotten.

Living your truth will help you see life in a different light — and seeing life differently?

It’s a skill that will set you free.

Mind Cafe

Relaxed, inspiring essays about happiness.

Alvin Ang

Written by

Alvin Ang

👑 Contestant on “The Apprentice.” Top Writer. For ghostwriting/copywriting enquiries, email: sgbjjopen@gmail.com

Mind Cafe

Mind Cafe

Relaxed, inspiring essays about happiness.

Alvin Ang

Written by

Alvin Ang

👑 Contestant on “The Apprentice.” Top Writer. For ghostwriting/copywriting enquiries, email: sgbjjopen@gmail.com

Mind Cafe

Mind Cafe

Relaxed, inspiring essays about happiness.

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