Stoic Philosophy for Entrepreneurs

Stoicism is a school of Greek philosophy that’s been copied by religions, other philosophies and “fix-yourself” experts for over 4,000 years.
The Stoics were philosophers, mostly Greek, who sought a practical path to happiness. Readers of early Stoics, such as Epictetus, will find commonalities with Christianity and Buddhism, religions that were formed centuries later.
The philosophy has several central tenets, but this one matters most for me: Things could always be worse.
I’m going to tell you why this attitude is critical in business, how it’s helped me overcome fear and why Stoic principles are influencing the fastest-growing trend among business founders.

“Do This Thing Now”

Most philosophers—especially the modern ones—fail to give actionable advice. They discuss reasons and norms. They talk around a subject.
For example, if you asked most modern philosophers, “What should I be when I grow up?” they might answer:
“Well, it depends on your definition of ‘I.'”
Or, “It depends on your definition of ‘be.'”
Or, “It depends on your definition of ‘grow up.'”
Stoic philosophers gave directives: “You should do this.”
Ask a Stoic philosopher “what should I be when I grow up?” and he or she would have told you the answer.
Stoic philosophy has risen in popularity recently, mostly in the form of daily admonitions to expect the worst and celebrate the best. That’s useful. But that’s not the real value of Stoic philosophy. The real value is its advice is directive. “Do this one thing now.”
I built our mentorship practice—and wrote each of my four books—with that principle in mind.
Early in my writing career, a reader pointed out that I often said “don’t do this” or “this is wrong” without providing the right answer. I immediately realized that I’d been taking the easy path: Any idiot can take shots at a strategy, and that’s what I’d been doing. But a great mentor can take that complex topic, teach it in an understandable way and then have the courage to say, “Do exactly this.”
That’s not easy because giving directives means accepting responsibility for the outcome. But direction is the only thing that has value.
Critics get attention on Instagram. Authors fill entire books with arguments about one topic or another. Low politicians attack others’ platforms. Speakers deliver long summaries of research. Some of those things are even true. But none it has value unless someone can say, “Do exactly this.”
In a world overflowing with ideas, arguments and noise, the principles of Stoic philosophy are clear. They’re not opinion; they’re directives. The value of “do exactly this” is so big that it’s usually the difference between success and failure.
Ryan Holiday wrote “The Daily Stoic” to provide clear daily directives for life.
I wrote “Founder, Farmer, Tinker, Thief” to provide clear directives for business.
Then I built the Two-Brain Growth ToolKit to make business directives easy to understand.


How to Use Stoicism in Your Life—And Your Business

Think of Stoicism as an operating system for your behaviors. Beneath the business tactics and strategies, Stoicism can be a platform on which you form long-term visions, deal with failure and “stay level” during the good times.

“The man who has anticipated the coming of troubles takes away their power when they arrive.” —Seneca

First, when making a key decision or facing a problem, consider the worst-case scenario.
For example, when an important staff member leaves, it can cause a ton of stress. To overcome the stress, you have to pick it apart. What’s so scary about the staff person’s leaving? Maybe you’re really worried he or she will take all your clients or criticize you in public. So ask yourself, “What’s the worst-case scenario?”
Will the person really take all your clients or just half of them? What if he or she did take half? Would those clients leave all at once or over the next few months? Which clients would leave first? How would they tell you? Put yourself in the frame and really imagine that conversation.
Then, take action: What can you do today to keep those clients?
If the person criticized you in public, what would happen? How would he or she do it—a post on Facebook? Comments to your colleagues in person? What would be said? What’s the worst-case effect it would have?
Then, decide: In the long run, are you better to acknowledge that this might happen and take no action? Are you better to respond? Can you write blog posts now explaining why you do things the way you do? In other words, can you eliminate criticism by reporting your flaws first?

“When you first rise in the morning, tell yourself: I will encounter busybodies, ingrates, egomaniacs, liars, the jealous and cranks. They are all stricken with these afflictions because they don’t know the difference between good and evil.” —Marcus Aurelius, “Meditations,” 2.1

People act in their own self-interest. You do it, and so do I. That means everyone is the central character in his or her own play; it also means that no one really pays much attention to you.
But we project knowledge: We think everyone knows what we know. We assume intent: We read negativity into a text when there really isn’t any. And we self-center: We think everyone considers the effect of his or her actions on us. They don’t. But it’s natural to think this way.
When you rise in the morning, you don’t need to assume that everyone you encounter will be a jerk. But you need to realize that you will encounter jealousy, crankiness and ingratitude. Accept it, and you’ll handle it when it comes.
You might also consider the difference between a person and his or her actions. You’re probably familiar with the commercial slogan, “You’re not you when you’re hungry.” Low blood sugar is a modifier of mood and attitude. So is fatigue, stress, exercise and distraction. You can like a person and still dislike his or her actions at times.

“Set aside a certain number of days during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: “Is this the condition that I feared?” … If you would not have a man flinch when the crisis comes, train him before it comes.” —Seneca

Prepare yourself for the worst, even while you hope for the best. Train yourself to deal with emotional stress by practicing physical stress in the gym. Visualize your worst-case scenario at every opportunity.
Take one day out of every month and fast. Wear the same clothes three days in a row. Place yourself in controlled situations of loss as practice for when the real situation arrives.
What would you do if you were fired today? What would you do if a new technology replaced yours next month? Immerse yourself in those scenarios. Our minds have an enormous potential to pretend. But the key isn’t to stay in a state of pessimism: It’s to solve problems before they happen. The real value of the Stoic mindset is the training opportunity: You can practice defeat and failure before they actually happen. Then, when they do, you’ll be ready.
Considering the worst-case scenario gives you the opportunity to do two things:

  • Break the problem down into its component parts without the lens of emotion. This makes the situation solvable.
  • Realize that even the worst case really isn’t that bad. In our society, entrepreneurs don’t starve.

Reading about the Stoics was life changing for me. I went from a high-stress micromanager to a focused mentor who can zoom out from the day-to-day stuff and see the big picture. My favorite is Epictetus, and here’s a shortcut: Read Tom Wolfe’s book “A Man in Full” to understand Stoic philosophy as it’s wrapped in a great story.

Other Media in This Series

The Four Fears of Entrepreneurship
The Beauty of the Bottom


One more thing!

Did you know gym owners can earn $100,000 a year with no more than 150 clients? We wrote a guide showing you exactly how.