06:00

Stoic Superhero #2: Diogenes On Mental Preparation

by Jon Brooks

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Diogenes is the most famous of the Cynics, a branch of philosophy that served as the precursor for traditional Stoicism. Diogenes was a bizarre fellow for a number of reasons. He lived inside a barrel and shunned any form of luxurious living. Diogenes only ate when he was starving hungry and drank when he was gaspingly thirsty. This allowed him to enjoy a simple cup of water as if it was the world’s most expensive wine.

StoicismDiogenesCynicismPhilosophyMinimalismGratitudeSimple LivingEquanimityHistorical FiguresAcceptanceStoic PhilosophyRadical AcceptanceDesires

Transcript

So we are exploring stoic superheroes and today we're going to be looking at Diogenes.

Diogenes the Cynic as some people called him.

He is the most famous of the Cynics and the Cynics were a school or a branch of philosophy that served as the precursor for Stoicism.

Diogenes was a very strange fellow by our standards and also by ancient standards for a number of reasons.

He lived in a barrel,

Yes a empty barrel like the kind of barrel that you would put beer or water in and he shunned any form of luxury.

Diogenes for example only ate when he was starving hungry and drank when he was gaspingly thirsty.

Why did he do this?

Well by following this protocol he was able to enjoy a simple cup of water as if it was the world's most expensive wine.

This goes back to the gap theory of happiness as William B.

Irvine calls it.

There are two ways we can be happy either by trying to get something on the other side of a gap between where we are and where the external object is.

So if I want luxurious wine I can try and get money and then acquire it and then drink it.

I close a gap that is only closed temporarily before a new shiny object appears or we can learn to want the things we already have.

And one way that we can learn to want the things that we already have is by meditating or experiencing abstinence or deprivation or loss.

And so when Diogenes only drank when he was thirsty he was able to reconnect to the amazing experience of drinking the thing that was easily available to him but the thing that most people had become jaded by and stopped appreciating and that is water.

The core of Diogenes' thought was based on his observation that quote bad men obey their lusts as servants obey their masters end quote.

And because we are so bad at controlling our desires we never find contentment.

This is why Diogenes was so intent on being the master of his own lusts and attachments.

Side question,

Do you consider yourself to be a master of your lusts and attachments?

It's a pretty epic goal and if you aren't a master of your lusts and attachments that's okay we're working on that we don't have to be perfect.

It's a big ambitious goal that we can have but it's still something that is noble to aim at.

Perhaps Diogenes' greatest and most memorable display of stoic superhero strength was in meeting with Alexander the Great.

Alexander was taught by Aristotle and had brilliant admiration for great thinkers.

One day when riding through Greece Alexander encountered Diogenes,

A philosopher he had heard many great things about.

The legend states that upon meeting Diogenes Alexander asked the philosopher if there was anything he could give him,

A gift.

Alexander at this point in time was the most powerful man in the entire world and he was also extremely hot tempered.

There were stories of Alexander having his best friends executed for disrespecting him.

So when he offered Diogenes a gift nobody would have expected the words that came out of this strange philosopher's mouth.

Yes,

Said Diogenes,

Stand a little out of my sun.

Diogenes was so steadfast in his cynic or stoic way of living he even risked the wrath of Alexander the Great to demonstrate it.

Diogenes was not someone who just lived his philosophy,

He was continuously on the lookout for opportunities to teach it and his meeting with Alexander presented one.

And it's one that we can continue to learn from now thousands of years later.

And it actually worked.

Alexander was so taken aback by this reply and was in so much admiration for the courage and the wit of Diogenes he said to his followers laughing,

But truly if I were not Alexander I would be Diogenes.

On a personal level the thing that inspires me most about Diogenes is his reply to a student who asked him what is the point of philosophy and Diogenes said to be prepared for every fortune and this is something that I try to practice with each day and when Diogenes is saying to be prepared for every fortune he's not saying to try and predict the billion different things that might happen and to be ready to counter those things like a chest grand master at life.

What Diogenes is saying is that he wants to develop so much equanimity,

So much acceptance,

So much radical gratitude that if the big tragedies in life befall him or the big wins so we're talking about illness,

Death,

Betrayal,

Exile,

Great wealth,

Fame,

Whatever the case,

Whatever the ups or the downs that fortune brings when they do come we will be prepared for them in our spirit,

In our mind.

We will be able to handle them with wisdom and that is the goal of philosophy and that is something that I think we can all strive for.

So take a brief moment now and ask yourself what could come today,

What could come tomorrow,

What could come in one week,

One month,

One year,

One decade.

Think of the possible great things,

Think of the possible misfortunate things that could come tomorrow.

Meet your Teacher

Jon BrooksCardiff, United Kingdom

4.7 (117)

Recent Reviews

Donna

January 10, 2026

Hi, Jon, On listening to your talk on Diogenes again (last time was 2 years ago, according to the date of the review I am writing over), I have to thank you for your entertaining and insightful discussion of Diogenes, obviously a unique and nearly incredible historical character! I laughed so much, and was inspired by Diogenes’s grit in bringing his message to the world. He is truly a fantastic phenomenon. I have unburdened myself of most of my accumulated possessions and appreciate the lightness of living without unnecessary things, but how the hell can anyone live in a barrel? Thanks, Jon, and I look forward to listening to more of your Superhero talks! Happy 2026, by the way! Donna Donna

TED

March 30, 2025

Great ! ...as usual.

Luis

May 9, 2024

Thanks

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© 2026 Jon Brooks. All rights reserved. All copyright in this work remains with the original creator. No part of this material may be reproduced, distributed, or transmitted in any form or by any means, without the prior written permission of the copyright owner.

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