Why Stoicism Is All About Optionality and Having Skin in the Game
By: Mahmoud Rasmi
Tags: Entrepreneurship, Stoicism, Life, Business, Startup

1. What Stoicism is NOT: (doers vs talkers)

No, Stoicism is neither centered around the virtue of pain and suffering for pain’s sake, nor about the unjustifiable containment of those.

Stoicism is not limited to the confines of academia either. Because what many ‘scholars’ overlook is that stoicism was a way of life, and not merely a subject for academic entertainment and endless mind games.

It should, thus, come as no surprise that instead of being a hot-topic in classrooms, stoicism has been adopted as Silicon Valley’s preferred school of thought for over two decades now.

I think that the reason why stoicism has been largely misunderstood, mainly by academics, is because its underlying principles are by and large derived from a practical rather than a theoretical understanding of the world around us.

To borrow from Nassim Taleb, stoicism is a philosophy for doers and not ‘tawkers’.

There’s a crucial difference between the academic sphere and industry that aggravates the disparities in how each of them approaches this particular school of thought. Namely, talkers (academics) are driven by a self-proclamation to moral superiority, while doers (industry) are driven by results and wealth management. This is the reason why I think Nassim Taleb, and The Daily Stoic are the best references on the topic in a contemporary sense.

Allow me to explain: one cannot really have a proper grasp of stoicism unless their downside (or the risk they’re taking) is significant. At the end of the day, stoics are mainly concerned with cultivating a mindset to confront any possible mishap, and adapting to it accordingly.

In the entrepreneurial world, the risks as well as the returns are very high. Entrepreneurs and enterprises alike find themselves continuously forced to make decisions to navigate their way through competition, streamline their daily operations, and improve their products. Surviving in the free market is a tricky business indeed.

The same applies to startups, which can either fail drastically, or hit through the roof overnight.

The best plan of action lies in endeavoring to protect oneself from any volatility that could potentially result in unfavorable asymmetries (aka, more losses than gains), by either making oneself robust (indifferent to the results), or antifragile (gaining from disorder). These concepts are explained in detail in Taleb’s work, and in Josh Hochschild delightful article Taleb the Philosopher.

Amidst such highly unpredictable environment and abundant volatility, stoicism comes out to the rescue as one of the best philosophies to hedge one’s downside. It is not the material downside we are talking about here, which is highly dependent on the savviness and risk-hedging skills of the stakeholder, but about a mental attitude towards the wide array of any possibly ensuing problems from one’s decisions.

When the stakes are that high, and involve likely scenarios of wealth accumulation or loss thereof, it takes a lot of effort to stay on track, and not lose one’s wits in the split of a second.

Unlike industry, though, academia’s downside is limited to a couple of scenarios, the worst of which — academically speaking — entails not being promoted or given tenure. The stakes are too low for professors, or senior administrators to become really aware of the importance, and relevance, of the principles promulgated by those who adopt stoicism as a way of life in the business world.

In other words, in order to apprehend the real worth of the stoic attitude, one ought to have skin in the game. That is to say, one ought to be willing to take responsibility for the downside as well as the upside of one’s ventures.

2. Stoicism as a cure

You might be wondering why choose stoicism of the myriad ancient philosophies concerned with how to live a good life including those of Socrates (and his disciple Plato) and Aristotle among others.

To begin with, the focal point of Ancient Greek ethics revolves around cultivating good character. This is true for many of the central figures of the time, including Socrates, Plato, Aristotle, Seneca, and Marcus Aurelius.

However, the difference lies in the conceptual underpinnings of the two camps these philosophers defended, namely, one theoretically oriented, the other practically so.

As Nassim Taleb perceptively points out in Antifragile, Socrates’ solicitation to examine oneself is a double-edged sword, more specifically in the area of moral philosophy.

This is because one would be prone to easily fall prisoner to a dialectic (argumentative) process that focused more on merely a theoretical pursuit of knowledge than its practical applications (praxis). This notwithstanding, examining oneself is an essential prerequisite to shake-off one’s dogmatism, and prejudiced preconceptions.

Aware of the potential problems arising within a Socratic or Platonic framework, Aristotle justifiably criticized Plato’s theory of forms.

Alas, Aristotle’s alternative account which offered a practical account of virtue ethics (the set of values and character traits highly praised in a society) fell short due to the complexity arising from the vagueness of a virtue that was to be only found in a balanced approach; in other words, in maintaining a mean between two extremes.

This viewpoint is wanting, precisely because it does not offer a clear set of criteria to act as a compass in determining one’s mean. Striving to keep a balance in a life governed by continuous flux and uncertainty is virtually an impossible feat.

Stoic ethics addressed the gaps in the accounts of their forerunners, and offered a better practical alternative concerned not so much with defining and maintaining some sort of balanced approach, as much as one that focused on cultivating a mindset against one’s possible downside.

The central thesis of Stoic moral philosophy resides in its promulgation of an argument the tenets of which comprise optionality, and hedging one’s downside.

“Seen this way, Stoicism is about the domestication, not necessarily the elimination, of emotions. It is not about turning humans into vegetables. My idea of the modern Stoic sage is someone who transforms fear into prudence, pain into information, mistakes into initiation, and desire into undertaking.” — Nassim Taleb, Antifragile

Unlike Aristotle’s average, stoic ethics provides a hands on attitude that is ultimately preoccupied with controlling one’s affections.

Such a state is achieved by cultivating an ascetic attitude towards life that seeks to live in accordance with nature (katà phusin.) This is primarily pursued by envisioning a life without possessions, and subsequently adopting an indifferent attitude towards wealth. The key point of such an exercise is not to rid oneself from wealth, but to learn how to cope with it in periods of riches and in privation.

Stoicism, thus, provides us with all the necessary practical tools to confront a frenetic, materially-driven life and lifestyles. Stoicism is neither about actively seeking pain in a masochist-like attitude, nor about “endur[ing] pain and pleasure without complaint.” It is also not about learning how to fend off our moral anger against an ‘unjust’ life.

Rather, stoicism is an ongoing quest for 1) increasing one’s optionality on all fronts of life, 2) cultivating a practical attitude to decision making (Taleb, 2012), 3) adopting a stance of indifference towards wealth, not by renouncing it, but by “continuously degrading the value of earthly possession” (Taleb, 2012).