A deep dive into the practical side of Stoicism

Over the past 5 years I’ve read at least 24 books a year. In 2023, I surpassed previous years by reading 64 books over a large, number of genres.

My main reading focus for 2023 wes personal efficiencies, software development, and Stoicism. Today, I’ll focus on the lessons from the stoic philosoply and its practical applications.

After reading ‘The Obstacle is the Way’, in 2022 I became intrigued by Stoic philosophy and read 10 different books on Stoicism in the year.

Below are the key insights I gained from the 10 books on Stoicism. Of note, many of the books below are written by Ryan Holiday who wrote ‘The Obstacle is the Way’, including ‘Life of the Stoics’, ‘Ego is the Enemy’, ‘Stillness is the Key’, ‘Courage is Calling’, ‘Discipline is Destiny’, and ‘The Daily Stoic’.

Next week, I’ll dive into the key learnings from my other 2023 books.

Life of the Stoics

Written by Ryan Holiday, author of ‘The Obstacle is the Way’, this book tells the history of Stoicism through the people who founded it, influenced it, taught it, and shaped it to the school of philosophy that we now associate the word ‘stoic’ with someone who is emotionless.

The book starts with Zeno the founder of Stoicism in Athens. It follows several generations of leaders of the school of Stoicism and how it spread to Rome, where many of the later stoics like Cato the Younger, Seneca, and Epictetus would extend and build on the philosophy. The book concludes with Marcus Aurelius, described as the Philosopher King, as we was both well versed and strongly practiced Stoicism and served as the Emperor of Rome during the height of the Empire.

Ego is the Enemy

Another book by Ryan Holiday, ‘Ego is the Enemy’ explains how our ego sabotages us and how to overcome our ego to succeed. Ego can masquerade as many things. Often it shows up as arrogance. It’s the “need to be better than, more then, recognized for”. But ego can show up in other, more subtle ways, such as telling ourselves that we’re special, that we deserve to succeed or that we were wronged by others.

Ego is at the root of most challenges. And it can be managed and overcome. To do so, we must

• Be Humble in our aspirations
• Gracious in our success
• Resilient in our Failvers

Stillness is the Key

Yet another Ryan Holiday book, Stillness is the Key dives into how to instill and nurture a sense of calm in the mind, body, and spirit.

This calm or stillness is the key to seeing clearly, being strategic, building good habits, and following the example of the Stoics.

Stoic Challenge

Everyday life presents an opportunity to practice being Stoic. Whether its being stuck in traffic, waiting in line at the grocery store, or dealing with an upset child, each moment offers us an opportunity to practice a stoic mindset. Viewing these moments as ‘Stoic challenges’ offer a way for us to set the proper mindset to approach these situations and remind ourselves to remain in control of our emotions.

Enchiridion & Teachings of Epictetus

After reading many modern books on Stoicism, I decided to spend some time reading ancient stoic texts including the ‘Enchiridion’ by Epictetus and the ‘Teachings of Epictetus’. The writings are dense and contain a few useful muggets including:

“You will be hurt when you consent to be hurt.”

“If you wish someone to be without faults, you are foolish.”

Discipline is Destiny

The Stoics valued 4 virtues: courage, temperance, justice, and wisdom. Temperance, or discipline as the author choose to call it, is about having command over one’s mind, body, and soul. “Most powerful is he who has himself in his own power.” - Seneca

We must exhibit discipline in all areas of life. Each area strengthens the discipline of other areas and conversely, a weakness in one area results in a weakness in other areas. “Once you compromise, you’ve been compromised.”

Courage is Calling

“There is nothing worth doing that is not scary.” It is up to us on how we respond to fear. Courage is about overcoming this fear and taking action anyway.

There are many aspects of courage, but one that resonated with me is the idea that our training and our preparation enables us to overcome our fear and push forward anyway.

The Daily Stoic

There’s no one single lesson that jumped out at me from this book. Instead, it was the experience as a whole of a daily reminder on some aspect of Stoicism that made this book a great read that I am continuing into 2024.

Anti Fragile

While not a book strictly on Stoicism I’m including it in this list as it references Stoic philosophy while also referenced in Ryan Holiday’s ‘Obstacle is the Way’. The concept of Antifragility is that there are things that get stronger by being exposed to stressors. The opposite of fragile, an item that breaks when exposed to stress is not robust. Something robust, at best, is unharmed by stress. The true opposite of fragile is something that improves by being exposed to stress. Conceptually, one can apply this idea to development teams. Such an application may be intentionally exposing the team to stress instead of protecting them like a ‘Scrum Mom’ would.