Why Stoic?


hhAncient philosophy stands the test of time because it works


The ancient Greek philosophy of Stoicism has enjoyed a resurgence in recent years, particularly among entrepreneurs, that’s only increased in the wake of a global pandemic. (The Times reports that sales spiked recently for works of two of the great Stoic philosophers, Seneca and Marcus Aurelius.)

While “influencers” like my friend Ryan Holiday, who’s written several books on the subject, have helped stoke renewed interest in these ancient teachings, they have stood the test of time because they work.

Stoicism is particularly attractive because it’s a practical philosophy created and taught by emperors, former slaves, and others who interacted in the “real” world.

The best possible life

The primary goal of the philosophy is to live as well as one possible can. Epictetus said the goal of a Stoic education was to create excellent people, not excellent philosophers.

Stoicism teaches us that rationality and knowledge are the highest virtues and will lead to a happy life. Modern-day philosopher Nasim Taleb defines a Stoic as someone “who transforms fear into prudence, pain into information, mistakes into initiation, and desire into undertaking.”

To do this, we must train ourselves as observers of the world; understand the things that are in and out of our control; and act on the things we can control.

Correct use of impressions

It starts with understanding what things are in your control. You must constantly monitor your thoughts and responses to understand your own programming and then intentionally program them differently. 

The “correct use of impressions” was the cornerstone of Epictetus’s teachings.

An impression is anything that pops into your perception, either from an external event or your own internal thinking. (If you’re driving and have to react to someone standing in the road, your perception of that person crossing the road creates an impression in your mind. If you get an email with unwelcomed news, your mind creates an impression and labels this information as “bad.”)

Anything outside of your control cannot be “bad,” because it’s part of a natural order of things. Even when a pandemic happens, killing hundreds of thousands of people all around the world, Stoics view it as a natural part of an interconnected world—not something to consider “bad.”

Rather than immediately labeling things in your head and reacting, ask yourself: “What if this weren’t bad?”

We all do this in retrospect. We see the good in a “bad” situation after the fact and end up thankful it happened. The trick to Stoicism is doing that in the moment

Negative visualization

For a Stoic, thinking only about the positive things you hope will happen leaves you woefully unprepared to deal with negative things that could happen—and, in fact, are destined to happen (more on this in a moment).

The Stoic practice of negative visualization helps you prepare for external events outside of your control.

Epictetus suggests that, when kissing your child goodnight, imagine they will die in their sleep. As horrible as this thought process is, this would put you in a better position to respond if it really did happen. You wouldn’t be totally blindsided. And the act of thinking the scenario through will make you more appreciative of the time you have.

Imagine the things that you’re afraid of and what you avoid thinking about: What will happen if you lose your job, or if people discover you’re not as smart as they think? Whatever your fears are, imagine them to the furthest extent, in detail.


The Stoics took this thinking a step farther. They believed all events are part of a destiny that’s laid out in advance. You might call it “God’s plan.” 

Marcus Eralius would say it’s nature, of which you are an appendage. Seneca taught that the world is connected. The universe is a tree, and we’re all branches on it. We exist for the purpose of the tree, not for ourselves.

If you believe in predestination, you believe you were put in whatever role you find yourself in for a reason. So, you must do that role well.

This sets up a paradox: Stoics believe in predestination (that you can’t change external events because they are meant to happen) and they feel a radical sense of responsibility to act when they are confronted by things that are in their control.

Responsibility to act

One of the major misconceptions about Stoics is that they are devoid of emotion or passion. While Stoicism teaches you to create emotional distance between the things you can’t control, it also teaches that you are duty-bound to act on things you can control. You have responsibility to act.

If you’re given the ball in a game, the thing that matters is what you do with the ball. That’s what’s in your control. Nothing else matters, not the game itself or the outcome.

Stoicism teaches that you have an obligation to strive for excellence, if nothing else.

There’s an idea in Stoicism that we’re all bartering for something throughout our lives and that the meaning of life comes from that barter. We’re bartering our life’s energy, trading it for things throughout our lives without even knowing it. For example, I consciously recognize the sacrifice and discomfort that comes with parenting; I intentionally trade my life’s energy so that my child can go do something in the world.

Stoics recognize that the point of life is to trade their life for something meaningful.