Cultivating Stoic Antifragility

Stoicism and Emotional Resilience

Caleb Ontiveros
Sep 20, 2019 · 6 min read
The resilient Phoenix

A previous article spent a lot of time discussing whether voluntary discomfort helps one become resilient. Resilience is a valuable trait, but it’s not nearly as valuable as becoming antifragile. What’s the difference? The resilient withstands stress, the antifragile becomes better because of it. In this article, I’ll focus on mental antifragility.

First, what is antifragility? The trader and philosopher Nassim Taleb explains the concept with three mythical figures: Damocles, The Phoenix, and The Hydra. The sword of Damocles represents fragility. In this myth, Damocles covets the king’s throne. The king notices this jealousy and opts to switch places with Damocles. Damocles is overjoyed and leaps over to the throne — only to find that there’s a sword tied to single strand of horses hair string above it. As kings throughout history have experienced, power is fragile. The Phoenix arises from the ashes every day. In this way it is beautifully resilient. It survives. The hydra, the many headed monster is resilient. When Hercules cuts off one of its heads, two more grow in its place. Stress empowers it.

This value of antifragility is also evident in many domains of life from business to performance, recall the quip:

Bad business are destroyed by failure, good businesses survive it, great businesses get better because of it.

Josh Waitzkin includes similar idea in his book, The Art of Learning. The chess prodigy and consultant, notes that there are three kinds of concentration:

  1. Distraction
  2. Hard Zone
  3. Soft Zone

The first kind is not concentration at all, it is Distraction. It is the sword of Damocles of focus. Any internal or external event can capture our attention when we’re completely distracted. The Hard Zone is a clenching and strong focus. When describing The Hard Zone, Josh talks about zooming into chess, shutting out the rest of his world and forcing the game to be the only thing there. The problem with this focus is that it can break. Though it may be resilient to most outside distractions, once a distraction is obnoxious enough, concentration is broken. When this happens it is immensely difficult to become concentrated again.

What Josh realized is that he wanted to be in the Soft Zone.

The Soft Zone is gentler and more open. Instead of zooming into the single aspect of the world it is broad. In this state, one focuses on the game, the game is the ultimate object of attention, but can let other sensations and thoughts go by. When this happens, one uses what would otherwise be a distraction in one’s favor. In Waitzkin’s words:

The nature of your state of concentration will determine the first phase of your reaction- if you are tense, with your fingers jammed in your ears and your whole body straining to fight off distraction, then you are in a Hard Zone that demands a cooperative world for you to function. Like a dry twig, you are brittle, ready to snap under pressure. The alternative is for you to be quietly, intensely focused, apparently relaxed with a serene look on your face, but inside all the mental juices are churning. You flow with whatever comes, integrating every ripple of life into your creative moment. This Soft Zone is resilient, like a flexible blade of grass that can move with and survive hurricane force winds.

We don’t have control of the external or internal environments. There will be stressors that arise from the external and internal worlds. This is why hard focus isn’t the best strategy. We can’t control our environment well enough. Hence, one needs to move to an antifragile mindset, Soft Zone. A mindset that is able to take advantage of aberrations in the environment and use them to our advantage.

This isn’t to say that one should always seek to become antifragile or that resilience is bad. In many cases, it makes sense to focus on becoming resilient first. Be sure that you can survive or live with the stressor, before you try to transform it into an advantage. But adopting an antifragile mindset is often exceptionally powerful. Consider this suggestive line from Nassim Taleb:

For life to be really fun, what you fear should line up with what you desire.

The antifragile Hydra

Cultivating an Antifragile Mind

How can one cultivate this mindset? Recalling the post on Stoicism and meditation, there are two kinds of practices, the cognitive and non-cognitive. During a non-cognitive exercise one trains the mind to act implicitly and automatically in the right ways. During a cognitive exercise one utilizes reasoning capacities to think through a given issue in an explicit and rational way. Exercises of both these kinds are legitimate and can be used to increase our mental antifragility.

A simple cognitive exercise one can do to practice antifragility is to pick a goal of yours. Remind yourself why it is something you value. Remind yourself of your explicit plan to achieve it — if you don’t have a plan, make one!

Now bring to mind actual or potential stressors. Ask, how can I use this to make me stronger? How can I use this to my advantage? How can I move with it? How can I ensure that the obstacle is the way?

For example, consider a stressor like an insult. One can be resilient to insults, merely ignoring them. Or one can use them to your advantage. This can look like using the insult as fuel. Using it to motivate you. An example of this, I have a friend who received advice from a mentor that he would never be able to raise funding for his idea. This was discouraging, but instead of giving up here he kept the email and would return to it now and again. He used it as a source of motivation. He eventually received funding.

If you’re familiar with Stoicism, you’ll know that planning for stressors like failure is a way to practice praemeditatio malorum, the premeditation of evils. In this variant we aren’t just preparing how to survive the worst, we’re determining how to use the worst case to our advantage.

One can train antifragility in a non-cognitive way through mindfulness meditation. In mindfulness meditation, one holds your attention on a meditation object such as the breath. While doing this one will inevitably become distracted. It’s easy to become frustrated when this happens. Instead of this, return to the present. Practicing the mental movement of noticing that one has become distracted and returning to the breath is key to meditation practice. One one hand, while meditating, you’re building the resiliency of your concentration: you’ll be able to resist distraction for longer periods of time. However, you’re also able to become antifragile and let distractions feed your focus. Distractions become triggers to return your attention to the meditation object.

A similar phenomenon occurs in exercise. As you exercise, you first learn to push past uncomfortable feelings of fatigue and pain. As you continue, you’re able to pick out the interesting and enjoyable parts of your sensation. What was at first a reason to quit, is now a reason to continue. What we are initially averse to can become desired — if we choose to apply our attention the right way.

In the words of Marcus Aurelius:

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

Stoicism — Philosophy as a Way of Life

Articles about Stoic Philosophy for modern living

Sign up for Stoicism – Philosophy as a Way of Life

By Stoicism — Philosophy as a Way of Life

What do you want to know about Stoicism? Learn about this ancient philosophy of life and how it's still relevant in the 21st century. Take a look

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Caleb Ontiveros

Written by

Founder of Stoa http://stoameditation.com/. Philosophy PhD dropout.

Stoicism — Philosophy as a Way of Life

Articles about Stoic Philosophy for modern living

Caleb Ontiveros

Written by

Founder of Stoa http://stoameditation.com/. Philosophy PhD dropout.

Stoicism — Philosophy as a Way of Life

Articles about Stoic Philosophy for modern living