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Mental Models

Stoicism’s Emotional Robustification

Stoicism teaches mental exercises to write off possessions and outcomes, countering the asymmetry of gains and losses. This makes one less fragile and emotionally independent from circumstances.

THE IDEA

Stoicism’s Emotional Robustification

Success brings an asymmetry: you now have a lot more to lose than to gain. You are hence fragile. Think of Damocles’ sword. There is no good news in store, just plenty of bad news in the pipeline. When you become rich, the pain of losing your fortune exceeds the emotional gain of getting additional wealth, so you start living under continuous emotional threat. A rich person becomes trapped by belongings that take control of him, degrading his sleep at night, raising the serum concentration of his stress hormones, diminishing his sense of humor, perhaps even causing hair to grow on the tip of his nose and similar ailments. Seneca fathomed that possessions make us worry about downside, thus acting as a punishment as we depend on them. All downside, no upside. Even more: dependence on circumstances—rather, the emotions that arise from circumstances—induces a form of slavery.

This asymmetry between the effects of good and bad, benefit and harm, had to be familiar to the ancients—I found an earlier exposition in Livy: “Men feel the good less intensely than the bad” (segnius homines bona quam mala sentiunt), he wrote half a generation before Seneca. Ancients—mostly thanks to Seneca—stay way ahead of modern psychologists and Triffat-style decision theorists who have developed theories around the notion of “risk (or loss) aversion,” the ancients remain deeper, more practical, while transcending vulgar therapy.

Let me rephrase it in modern terms. Take the situation in which you have a lot to lose and little to gain. If an additional quantity of wealth, say, a thousand Phoenician shekels, would not benefit you, but you would feel great harm from the loss of an equivalent amount, you have an asymmetry. And it is not a good asymmetry: you are fragile.

Seneca’s practical method to counter such fragility was to go through mental exercises to write off possessions, so when losses occurred he would not feel the sting—a way to wrest one’s freedom from circumstances. It is similar to buying an insurance contract against losses. For instance, Seneca often started his journeys with almost the same belongings he would have if he were shipwrecked, which included a blanket to sleep on the ground, as inns were sparse at the time (though I need to qualify, to set things in the context of the day, that he had accompanying him “only one or two slaves”).

I have applied this brand of Stoicism to regain some psychological control over the randomness of life. I have always hated employment and the associated dependence on someone else’s arbitrary opinion, particularly when much of what’s done inside large corporations violates my sense of ethics. So I have, accordingly, except for eight years, been self-employed. But, before that, for my last job, I wrote my resignation letter before starting the new position, locked it up in a drawer, and felt free while I was there. Likewise, when I was a trader, a profession rife with a high dose of randomness, with continuous psychological harm that drills deep into one’s soul, I would go through the mental exercise of assuming every morning that the worst possible thing had actually happened—the rest of the day would be a bonus. Actually the method of mentally adjusting “to the worst” had advantages way beyond the therapeutic, as it made me take a certain class of risks for which the worst case is clear and unambiguous, with limited and known downside. It is hard to stick to a good discipline of mental write-off when things are going well, yet that’s when one needs the discipline the most. Moreover, once in a while, I travel, Seneca-style, in uncomfortable circumstances (though unlike him I am not accompanied by “one or two” slaves).

The aim of mentally writing off belongings is to reduce the hold that possible losses have over daily life.

When to use it

  • Before a high-stakes meeting or negotiation, mentally prepare for the worst outcome to reduce fear and perform more freely.

  • When acquiring a new material possession, immediately imagine losing it to decrease its emotional hold over you.

  • When starting a new job or project, accept the possibility of failure while continuing to work toward success.

  • When making a risky decision with clear downside, use the worst-case mental exercise to evaluate if the risk is acceptable.

FROM THEORY TO EVERYDAY LIFE

In practice

01

Seneca’s Travel Preparation

Seneca started journeys with minimal belongings, as if shipwrecked, to reduce attachment to possessions and avoid the sting of loss.

02

Resignation Letter in Drawer

Before starting a job, the author wrote a resignation letter and locked it away, feeling free and less dependent on the employer's opinion.

03

Morning Worst-Case Exercise

As a trader, the author mentally assumed every morning that the worst had already happened, treating the rest of the day as a bonus to reduce anxiety from randomness.

✳

A MOMENT TO REFLECT

Put it to work.

  1. What possessions or circumstances do you depend on that make you emotionally fragile? How could you mentally write them off?

  2. How would your emotional state change if you assumed the worst possible outcome had already occurred today?

  3. In what areas of your life do you experience asymmetry between potential gain and loss? How can Stoic exercises help balance this?

Connected ideas

Another lens can bring the same problem into focus.

CONTINUE THE CONVERSATION

Source texts

  • Antifragile (Nassim Nicholas Taleb)
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