Stoicism – The Most Antifragile Mental Operating System (Stoicism Explained with Antifragility)

Siim Land

The nature of the world is that change is inevitable and that we can never be sure what’s going to happen to us. Excuse my French, but, sh*t is going to hit the fan sooner or later. When it does, we will either perish or succeed. That depends on whether or not you have an antifragile mental operating system.

Is there a way to not be as negatively influenced by this? Can we still face challenges, life’s turmoil and emerge from the fray better than before? The answer to that is yes.


The term was coined by Nassim Nicholas Taleb in his bestselling book Antifragile: Things That Gain from Disorder. It’s a step beyond robustness because it actually benefits from chaos and adversity. So it is with stoicism.

Taleb introduces the book as: “Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.”


Antifragility is the ability to emerge as a victor from adverse circumstances stronger than ever before. No matter what happens to you, you’ll benefit from the situation. Think of the Greek mythical monster hydra, that had several heads and grew each of them back once you cut one off.

Meet Stoicism

Stoicism is a school of Hellenistic philosophy founded in Athens by Zeno in the early 3rd century BC. It’s one of the best mental operating systems to have because of its antifragility.

The Stoics considered destructive emotions to be the result of errors in judgment, the active relationship between cosmic determinism and human freedom, and the belief of acting virtuously in accord with nature. For a good life, one had to understand the natural order of things because everything was rooted in it.

Stoicism the Most Antifragile Mental Operating Systems
Stoicism the Most Antifragile Mental Operating Systems

Stoicism became more dominant later in Rome than in its birthplace Greece. Writers like Seneca and Epictetus considered the sage (the one who knows virtue and acts according to it) immune to misfortune because virtue is sufficient for happiness. Marcus Aurelius is also one of the most important stoic philosophers.

How does it work?

Basically, stoic thought enables you to understand that “sh*t happens” and you can’t really do much about it. You’re inevitably going to miss busses, lose your wallet, face challenges, have to do hard work to succeed and get your heart broken many times. It’s a way to pre-emptively come to terms with the fact that adversity is going to happen and you can actually benefit from it.

The Urban Dictionary defines the word “stoic” as such.


Someone who does not give a shit about the stupid things in this world that most people care so much about. Stoics do have emotions, but only for the things in this world that really matter. They are the most real people alive.

Group of kids are sitting on a porch. Stoic walks by.

Kid – ‘Hey man, yur a fuckin faggot an you suck cock!’

Stoic – ‘Good for you.’

Keeps going.

Challenges Augment You

In Marcus Aurelius’ book Meditations, there is a phrase which goes like this:

“The impediment to action advances action. What stands in the way becomes the way.”

This quote is also what Ryan Holidays bestselling book The Obstacle is the Way is based upon. He’s one of the leading modern day stoics.

Have you ever had a negative experience which later turned out a lot better than you expected? During the actual event we’re cursing and struggling, but in retrospect, we realize that we’ve gained a lot of wisdom from that challenge and actually emerged as a better person. A person stranded on an island in the middle of the ocean will have to fight for their survival. Talk about another bestselling book or blockbuster movie, if they survive, that is.

Whatever the case might, there is still so much to learn from challenges and obstacles. As in the case with resistance training, once overcome, we’ll get stronger and better. Without the stimulus for growth, we won’t be able to improve.

Why You Should Want it to Be Tough

I like to say that: “Adversity is to be expected and yearned for.”

It’s not the challenge per se that makes us better but the overcoming aspect of it that does so. In difficult situations and in adverse conditions we’re forced to adapt to novel stimuli. As a result, we bulletproof ourselves to whatever might happen to us.

I’ve used stoic techniques to come to terms with the fact that sh*t will hit the fan sooner or later. Having pre-emptively conditioned myself, I’m able to suck it up and deal with it. Like the saying goes: “When the going gets tough, the tough get going,” and “Tough times don’t last, tough people do.”

If you keep the worst case scenario constantly in the back of your head, the Stoics tell us, we become immune to the dangers of too much positive thinking, which isn’t a realistic account of the world. If you were to only expect the good, then you’ll lead yourself to despair because anything less than ideal will become unbearable. That’s why someone who has never had to work hard a day in their lives will be remorseful once they’ve lost their riches. Only by envisioning and experiencing the bad can we truly appreciate the good. Marcus Aurelius started each day telling himself: “I shall meet with meddling, ungrateful, violent, treacherous, envious, and unsociable people.”

Antifragile by Thought

That’s why stoicism is the best mental operating system to have. You’re antifragile and bulletproof to external events. Whatever happens, you can only gain from them. The reference experienced you’ll gather will give you knowledge about the nature of change and teaches you how to overcome obstacles, in spite of their seemingly insurmountable size.

What makes stoicism work is also the concept of memento mori, the remembrance of death. It’s a meditative exercise that’s supposed to remind the person that everything in the world – the body, career, reputation, even family – should not be the primary focus of our minds, nor the source of our happiness because these things can be swept away by death in an instant.

Instead, what Socrates also declared, the purpose of philosophy, was to teach humans to free the divine part of themselves – their soul, the spirit – from the body and the passions. As a result, we would become less like animals, and more like gods thanks to our heightened consciousness. One way to do that was to remind oneself that the organic body is just a vehicle that will soon meet its expiration date.

Reminding ourselves that one day we’re going to die is almost enlightening and will definitely benefit our happiness. It prevents us from getting distracted by things that don’t serve us nor contribute to our existence. We attain a new perspective and desire to follow our calling and pursue becoming more conscious.


Stoicism isn’t dark or dreadful. It might seem that by focusing on the negative aspect of events we’re being overly pessimistic or full of apathy. That’s not the actual case. It’s actually a way to make yourself happier. If you’ve already expecting your experiences to be less than ideal, then anything beyond that is already an immense improvement. You’re being more grateful for what you have and can understand how fortunate you really are.

Seneca would habitually condition himself with poverty: “Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: “Is this the condition that I feared?””

He was the richest banker in Rome, yet deliberately conditioned himself like a slave, every once in a while. He achieved 2 things:

  1. The difficult experience was constantly etched into his mind, which made him not to take his fortune for granted, and
  2. he was capable of surviving in adverse conditions, which made him bulletproof against anything that might have happened. His happiness actually improved because his state of mind was satisfied with virtue, not material belongings, and his actual affluence was exponentially higher than he was expecting to have.

The Antifragile Mental Operating System Takeaway

We should first understand that change is inevitable. Negative events are part of the unexpected conduct of the cosmos. The desire to have our own way comes from fear. Our mind wants to preserve energy not expend it on adapting to novel stimuli. It’s an evolutionary predisposition, which makes us want to stay in our comfort zone. However, that implies to stagnation and isn’t where growth happens.

Secondly, we should yearn for adversity, as it will condition us to become better. What stands in the way becomes the way. If we get used to difficulties, then we improve our ability to deal with them. Overcoming resistance enhances our strength and muscles. Climbing over obstacles augments our mind and mental toughness.

Thirdly, don’t take things for granted. Condition yourself to be happy with less, not more. Too high demands will make it more difficult for you to maintain your happiness. If you’re used to less ideal conditions, then anything beyond that is already an immense improvement. On the flip side, if you’re constantly having it easy and well off, then you’ll fall face down on the ground once something unpredictable makes you lose all your riches.

Join the Body Mind Agoge, so that you could learn more about empowering your performance both physically and mentally, as well as spiritually.

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I’ve written several blog posts about this, in which I go into further derail on how to use different stoic techniques to become antifragile.

The Art of Overcoming Negative Events Before They Happen.

How to Make Our Life Less Comfortable.

How to Turn a Negative Experience into a Positive One.

  • Dean

    wow so powerful post, keep more (I came from reddit so keep post there more on stocism sub and on others as well!)

    • Siim Land

      Thanks! Glad you liked it. More stuff coming.