Stoicism for Leaders and Entrepreneurs

Stoic Philosophy and Psychology in Business

Stoic Philosophy and Psychology in Business

Every day, it seems, more entrepreneurs and leaders in the business community are becoming interested in Stoic philosophy. Stoicism offers a whole philosophy of life, which promises to help us attain not only greater emotional resilience in the face of adversity, but also a deeper sense of purpose and meaning in life, and in our work.

The Wall Street Journal published a review of my book How to Think Like a Roman Emperor: The Stoic Philosophy of Marcus Aurelius, which perhaps sums up Stoicism’s contemporary appeal.

Marcus is remembered not merely for his long reign but for his practice of Stoicism — a school of philosophy founded in Athens by Zeno of Citium around 300 B.C. Stoicism counsels its adherents not to place too much importance on things outside their control. Rather than fret about the frustrations of our daily lives, the Stoics advise, it is better to bring one’s will in accord with nature and approach the present moment with composure. […] Marcus’ worldview was not an idle intellectual exercise […] but a form of wisdom forged by real-world experiences of friendship, loss and crisis. — The Wall Street Journal

The transcript of an interview about Stoicism that I did recently for Wharton business school’s radio station was published on the World Economic Forum’s website. I was asked how Stoicism works in the business community…

It’s a strange thing. I didn’t anticipate this, but one of the biggest groups of people interested in it seems to be millennials who work in the tech industry. I feel like it [kind of took] root in Silicon Valley. Where I live in Toronto, I meet a lot of young people working in software development or the tech industry in general who are particularly drawn to this philosophy.

Tim Ferriss & Ryan Holiday

Most of the younger people I meet who are into Stoicism actually say they were introduced to the philosophy through references made to it by Tim Ferriss or Ryan Holiday.

Ferriss has a whole section of his website devoted to Stoic resources, including the free PDF and (paid) audiobook versions of his own Tao of Seneca book. Tao of Seneca consists of the famous “moral letters” of Seneca to his friend and fellow-Stoic Lucilius, alongside which Ferriss has included thoughts from various “modern Stoics”. (One of the chapters in Tao of Seneca contains an interview I gave for Ryan Holiday’s The Daily Stoic website.) Ferriss says that his own life was transformed in 2004 when he discovered the writings of Seneca.

[Stoicism] can be thought of as an operating system for thriving in high-stress environments. At its core, it teaches you how to separate what you can control from what you cannot, and it trains you to focus exclusively on the former. — Tim Ferriss, The Tao of Seneca

However, Ferriss says that in addition to building emotional resilience for coping with negative experiences in life, “Stoicism can also be used to maximize the positive”.

For this reason, Stoicism has spread like wildfire throughout Silicon Valley and the NFL in the last five years, becoming a mental toughness training system for CEOs, founders, coaches, and players alike. Super Bowl champions like the Patriots and Seahawks have embraced Stoicism to make them better competitors. In my own life, the results have been incredible. — Tim Ferriss, The Tao of Seneca

Ferriss actually says that looking back on the preceding two decades of his life, he credits “nearly all of the biggest successes — and biggest disasters averted — to my study of Stoicism and, specifically, the writing of Seneca.”

Tim Ferriss also recommends the works of Ryan Holiday, author of The Obstacle is the Way and co-author (with Stephen Hanselman) of The Daily Stoic. In his article Stoicism 101: A Practical Guide for Entrepreneurs, Holiday writes:

For those of us who live our lives in the real world, there is one branch of philosophy created just for us: Stoicism. It doesn’t concern itself with complicated theories about the world, but with helping us overcome destructive emotions and act on what can be acted upon. Just like an entrepreneur, it’s built for action, not endless debate. — Ryan Holiday, Stoicism 101

Holiday’s bestselling books have introduced countless people to Stoicism, especially younger generations of readers. Whenever I speak to people who are into Stoicism and work in the tech industry, in particular, I can guess that they’ve probably read The Obstacle is the Way.

Business Leaders on Stoicism

Several prominent CEOs have likewise spoken about the influence of Stoic philosophy on their lives. For example, in a recent interview, Jules Evans asked Jonathan Newhouse, the CEO of Condé Nast, how he got into Stoicism.

It was 1999. I ran into Alain de Botton in a restaurant. He was having dinner with a friend of mine. He said he was working on a book of philosophy, and mentioned Seneca, who I’d never read. I went out and brought Seneca’s Letters From a Stoic. And it just blew me away. I found it impeccably logical. That led me on to Marcus Aurelius and Epictetus. I read just about everything I could. Now I usually take one of the Stoic books with me when I travel. I incorporated it into my thinking and it’s shaped the way I think and interact with the world in a very positive way.

He explains very succinctly how Stoic philosophy influences his worldview:

People devote a lot of time and emotional effort to things that are beyond their control — what other people do, how other people react to them, even the weather. And they set themselves up for pain, anxiety, disappointment and fear. The Stoics recognised that it was foolish, or counterproductive, to attach oneself to things that are beyond one’s control, when there are things within one’s control — one’s thoughts, attitudes and moral purpose.

I loved the idea that you could make your goal to live a life of moral purpose. I was very taken with the ethical and moral point-of-view of Stoicism. When you read the Stoics, you often come across the word ‘virtue’. They saw the goal of the wise person as to lead a virtuous life. Today, the word ‘virtue’ is almost never heard, except ironically. If you asked 100 people what their goal was in life, hardly any would say leading a virtuous life.

Eugenio Pace, the CEO and co-founder of Auth0, likewise writes in a Forbes article titled Can Philosophy Influence Business? Here’s What The Stoics Have Taught Me,

Being an entrepreneur in the tech world means creating new experiences, opening untapped markets, and forging new paths. Starting a business is risky and involves charting foreign territory. That’s why I find the teachings of the Stoics important for remaining grounded through tumultuous endeavors. — Eugenio Pace in Forbes

Pace adds the following Stoic advice for coping with stress at work,

Epictetus said, “Some things are up to us, and some are not up to us.” As a fellow technology entrepreneur, founder and CEO, the best advice I have for liberating yourself from anxieties that make you less happy and productive is simple: Stop worrying about what you can’t control.

Some More Articles on Stoicism

Forbes magazine have actually covered Stoicism several times in recent years. Chris Myers, the co-founder and CEO of BodeTree, writes in How One Struggling Entrepreneur Found Solace in the Ancient Philosophy of Stoicism,

Stoicism, at its core, reminds us that life and everything in it, is impermanent. Focusing on our circumstances or pinning our happiness on the attainment of possessions is a surefire recipe for disappointment. The Stoics, such as Roman Emperor Marcus Aurelius, instead encourage us to free ourselves from the control such pursuits exert over us and focus on the things that are in our direct control: our thoughts, feelings, and desires. In this sense, Stoicism is uniquely suited to serve the needs of entrepreneurs. — Chris Myers in Forbes

He concludes, “In helping us to identify what we can control in our lives and to find happiness in what we already have, Stoic philosophy allows us to mute the terrible emotional roller coaster that is entrepreneurship.”

Stoicism has also been applied to quite specific challenges in the modern workplace. Adam Piercey, an engineering technologist, wrote a recent Medium article on Stoicism in Tech for Better Programming, which explores specific ways Stoicism can be used to handle stressful situations like peer review. He applies wisdom from Marcus Aurelius to the challenge of receiving critical feedback a software engineer.

As Marcus said, you should “immediately consider on the basis of what opinion about good or evil he did wrong.” If you choose to view the feedback as constructive and positive, you can learn and proceed. The Stoics believed that we should welcome criticism in this spirit and that our role is to make the best use of criticism. If you begin any feedback experience with the mindset that it comes from a place of good intentions, there is a significant opportunity to learn and grow. — Adam Piercey in Better Programming

In another Forbes article, titled Five Reasons Why Stoicism Matters Today, Rob Goodman and Jimmy Soni, authors of Rome’s Last Citizen, argue that Stoicism is “a philosophy for leadership”.

Stoicism teaches us that, before we try to control events, we have to control ourselves first. Our attempts to exert influence on the world are subject to chance, disappointment, and failure — but control of the self is the only kind that can succeed 100% of the time. From emperor Marcus Aurelius on, leaders have found that a Stoic attitude earns them respect in the face of failure, and guards against arrogance in the face of success. — Goodman and Soni in Forbes

In an article titled Why Today’s Best Business Leaders Look to Stoicism, Aytekin Tank, the founder and CEO of Jotform, writes:

[W]hat if I told you that there’s a school of philosophy dating back to ancient Greece that can help you handle all of these obstacles on a daily basis and, as a bonus, may even enrich your quality of life? And better still, you don’t have to be a scholar to figure out how to use it. It’s called Stoicism, and it’s a practical philosophy that’s used by some of today’s greatest thinkers and business minds, including Tim Ferriss, Ryan Holiday, Arianna Huffington and Jack Dorsey. — Tank in Entrepreneur

He lists the main ways in which Stoicism can help entrepreneurs as:

  1. Setting priorities, by focusing on what’s essential

  2. Curbing stress, by distinguishing what is up to us from what is not

  3. Stopping procrastinating, by being aware of our own mortality and the precious nature of time

  4. Managing fear, by premeditatio malorum or the systematic anticipation of future misfortunes

A few years ago now, Carrie Sheffield, founder of the digital media startup Bold TV, interviewed me for a Forbes article titled Want An Unconquerable Mind? Try Stoic Philosophy. She opens by stating that the ideas of ancient Stoics “hold fascinating promise for business and government leaders tackling global problems in a turbulent, post-recession slump.”

Prominent business thinker Nassim Nicholas Taleb praises Stoic philosophy in his Antifragile: Things That Gain from Disorder, a book that Stoic Week organizer Donald Robertson says nudged many curious readers toward Stoicism. Robertson, a Scottish-born therapist and classics enthusiast, led workshops on psychological resilience for managers at oil giant Shell called “How to think like a Roman Emperor,” based on the life of stoic philosopher-king Marcus Aurelius. — Sheffield in Forbes

Taleb’s bestselling book, Antifragile, mentioned above, contains a whole chapter dedicated to his Stoic hero, Seneca. Indeed, Taleb actually says that Seneca “solved the problem of antifragility […] using Stoic philosophy”. Taleb rightly emphasized that Stoic philosophy is not about being totally unemotional, rather it’s about replacing unhealthy emotions with healthy ones.

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. — Taleb, Antifragile

We went on to discuss the famous Stoic “Dichotomy of Control” and how it might be related to the psychology of leadership.

“Anyone in a leadership role must come to terms quickly with the paradox of their position: that leaders must wield power but that often so much that happens lies outside of their control,” Robertson told Forbes. “How do we accept the limits of our power without slumping into passivity?” — Sheffield in Forbes

She also asked me about common misconceptions of Stoicism.

Robertson said people sometimes confuse stoicism with submissiveness, but calls this “a very superficial misunderstanding.” Students of ancient stoicism tended to be sons from wealthy, cosmopolitan families. Many went on to rule empires or advise great leaders in commerce and war. “Can you point to a single historical stoic who sat on his hands?” quips Robertson… “It’s just not in the nature of their philosophy to be doormats or stay-at-home types.”

The Economist’s 1843 Magazine ran an article recently on “Stoicism’s revival” called Life Lessons from Ancient Greece, which quoted me on the links between Stoicism and modern cognitive-behavioural therapy.

Many modern stoics argue that this doctrine has already been partially revived in the form of cognitive behavioural therapy (CBT), the “problem-focused” therapy now widely seen as psychology’s best weapon against depression, anxiety and every kind of unhelpful thinking. Like stoicism, CBT encourages practitioners to distinguish between events and perceptions, and nearly every CBT textbook contains some version of Epictetus’s dictum: “Men are disturbed not by things, but the views they take of them.” Yet although the founders of CBT openly acknowledged the influence of stoicism, they tended to adopt the techniques without reference to the wider moral framework. “Stoicism transcends most modern self-help and therapy by offering the view that much of our emotional suffering is caused by false values, such as egotism, materialism or hedonism,” says Donald Robertson, a cognitive-behavioural psychotherapist who is one of the organisers of Stoic Week. — Rowland Manthorpe in The Economist

Another good source of information is Modern Stoicism, a nonprofit organization run by a multi-disciplinary team of volunteers who carry out research on Stoicism and disseminate information on its application to modern-day living. Modern Stoicism run the annual Stoicon conference and multiple Stoicon-x mini conferences in different cities around the world. They also run the annual Stoic Week online course, in which over eight thousand people took part last year. The figures from these events show that Stoicism is continuing to experience a revival and it’s often among entrepreneurs and leaders in business that it’s catching on the most.

The Leadership Qualities of a Stoic Emperor

Many of the articles above discuss ways in which the basic concepts and practices of ancient Stoicism can be of benefit in the work environment today. However, I’ve also tried exploring the relevance of Stoicism from a rather different perspective by looking at the qualities of a good ruler which Marcus Aurelius sought to learn from his adoptive father and predecessor the Roman emperor Antoninus Pius.

We can summarize advice based on the leadership qualities Marcus admired as follows:

  1. Get along with other people

  2. Be hardworking and conscientious

  3. Don’t seek praise or flatter others

  4. Don’t be afraid of criticism

  5. Be content with the simple things in life

You can read more about how Marcus defined those qualities as exemplified by the Roman emperor Antoninus Pius in my previous Medium article on the subject. They’re all consistent with the teachings of Stoicism, although Antoninus Pius himself doesn’t appear to have been a Stoic.

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