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A Guide to Stoicism for Creatives, Entrepreneurs, and Freelancers

Photo: Unsplash

I’ve been “let go” several times.

I started a business that consumed five years of my life and well over six figures of investment money and failed. Anxiety and depression have been a post-college issue that I’ve had to learn how to manage. I’ve worked multiple jobs doing 12-plus-hour days, six days a week, as a freelancer and independent worker with perpetual instability for the past three years.

I grew up in a privileged family and subconsciously assumed life would always be that way. I was wrong.

I chose this life. I chose to build a portfolio career compiled from a collection of entrepreneurial, freelance, and independent work. So a lot of the challenges of adulthood are of my own making.

Therefore, it’s my responsibility to learn resilience. This led me to Stoicism.

You may have heard a bit about Stoicism recently. It’s making a comeback in personal development circles; notably, Tim Ferriss is a big fan. But the philosophy has been around for ages. Literally.

Zeno of Citium founded Stoicism in Athens during the early 3rd century BC.

It just so happens that the principles of Stoicism are dead-on relevant to people in the creative professional realm (entrepreneurs, intrapreneurs, freelancers, and independent workers). I think the increased interest is tied to a rise in both entrepreneurship and freelancing.

The Stoics focused on a few things:

  1. How can we lead the best life possible?
  2. How can we become better human beings in our everyday life?
  3. How can we manage our mood effectively and not allow emotion to cloud our judgement, decisions, and thinking?
  4. How can we digest failure, turn it into good, and adapt when necessary?

This philosophy is geared to equip its advocates to remain levelheaded in the midst of life’s natural twists and turns. We don’t have control over what happens to us, only how we respond.

The main Stoic philosophers were Marcus Aurelius, Seneca, and Epictetus.

The Roman emperor Marcus Aurelius wrote about restraint, compassion, and humility. Seneca, a statesman and adviser to the emperor Nero, documented his perspective on things like friendship, moral obligation, gratitude, the importance of daily walks, reviewing your day’s work, and rest. Epictetus was born a slave; with permission from his owner, he studied Stoic philosophy and went on be a founder of a philosophical school teaching Stoicism. Epictetus left simple but remarkable teachings, like the importance of mental contrasting, valuing forgiveness, and continually editing our lives to make sure our energy is focused only on the essentials.

These three men became mentors for me by way of their work preserved in essays, books, and letters.

What I appreciate most about the Stoic tradition is that it’s a philosophy built for the practicalities of life, not for academic debate. It’s not some impossible dialogue that only a few lifelong trained philosophers can digest. Instead, Stoicism is accessible.

What follows are lessons from the Stoics that have helped me and other creatives, entrepreneurs, and freelancers from my coaching practice.

Level Down to the Essentials

There’s buzz around 10x-ing your life. The paradox, however, is that doing so requires you to do less — less of the nonessential. The through-line among peak performers is repeated bouts of focus over a long period of time. I believe being focused is a form of tranquility, popularly known as “flow,” which also happens to be the nectar of deep work. Marcus Aurelius advocated leveling down to achieve tranquility:

If you seek tranquility, do less. Or (more accurately) do what’s essential. Do less, better. Because most of what we do or say is not essential. If you can eliminate it, you’ll have more tranquility. But to eliminate the necessary actions, we need to eliminate unnecessary assumptions as well. — Marcus Aurelius, Meditations

Level down and do less of the nonessential to experience tranquility more often. Our focus depends on it.

Cultivate an Attitude of Gratitude

That headline runs on the border of being an eye-rolling platitude.

However, the evidence supporting a daily gratitude practice is substantial. A daily gratitude practice has been show to improve sleep quality, reduce snooze time, and increase the likeliness of consistent exercise and healthy eating. Lastly and perhaps most significant, routinely giving thanks is correlated with emotional stability, reduced stress, and lowered anxiety. These modern-day discoveries are backed by the primitive wisdom of Seneca:

In all things we should try to make ourselves be as grateful as possible. —A letter from Seneca to his friend Lucilius

A gratitude exercise doesn’t need to be grandiose. Being thankful that you have internet connection to read this article is a good place to start.

A simple practice I follow is listing one thing I’m thankful for each day. The key is to list something different every day. Here’s my entry from July 27, 2017:

Give Your Mind Regular Breaks

Back in 2010, I started a business built on naive enthusiasm. It was all passion and no skill.

The business was fine for a while, but toward the end, I flamed out and became miserable. I burned out.

Since then, I’ve taken a deep dive into peak performance to avoid another miserable failure like that.

The mind must be given relaxation — it will rise improved and sharper after a good break. —Seneca, “On Tranquility of Mind

This flies in the face of conventional Western wisdom that more is better.

My curiosity then led me to ask, “How do you take good breaks?” It turns out that we are wired with a biorhythm that supports emotional and mental labor.

When we orient ourselves around this concept, we are more likely to avoid burnout. Jim Loehr, author of The Power of Full Engagement, tells us to look for signals of fatigue every 90 to 120 minutes: a yawn, a stretch, hunger pangs, increased tension, difficulty concentrating, an inclination to procrastinate or fantasize, or a higher incidence of mistakes.

These fatigue signals tell us that it’s time to step away and engage in renewal.

Your renewal tactic does not need to be complex. In fact, the more familiar your choice, the better. Choose simple exercise like walking, guided meditation (so you don’t have to think about what to do), or talking to a friend about non-work-related stuff. The aim is to step away from the work while using minimal willpower or mental energy to preserve those resources when you return to work.

Giving your mind regular, intentional breaks is a solid approach to avoiding burnout. I wish I would have known about this approach back in 2010.

Brace Yourself for Uncertainty

In his Meditations, Marcus Aurelius wrote, “The art of living is more like wrestling than dancing, because an artful life requires being prepared to meet and withstand sudden and unexpected attacks.”

In her book, The Positive Power of Negative Thinking, Julie K. Norem unpacks the concept of defensive pessimism — considering the worst-case scenario so you can plan how you’d handle it.

This doesn’t erase the possibility of uncertainly. Rather, it shifts your response from frantic and surprised to calmly prepared. This provides peace of mind. Research shows that, on average, people who never worry have lower job performance than those who use their anxiety to prepare for uncertainty.

Recognize That Life Goes On After Failure

I spent five years of my life on that one failed business, and I had nothing to show for it. Or so I thought.

At first, the disaster was an open wound.

With time, the wound turned into a scar. And slowly, I became curious about why things turned out the way they did. One thing I discovered is that life goes on after a failure — even the big ones.

It’ll hurt like hell, but you can come back from it. The key is to mentally return to what is true day after day, and sometimes hour after hour. Reminding myself of the things I had agency over helped me recover from the failure.

Does what’s happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness, and all other qualities that allow a person’s nature to fulfill itself? So remember this principle when something threatens to cause you pain: the thing itself was no misfortune at all; to endure it and prevail is great good fortune. —Marcus Aurelius

This entire process of healing wasn’t pleasurable for me, but it taught me how to be resilient. Because of that, it brings me joy to know that I can bounce back after taking a hit to the chin.

Before You Say Yes, Survey the Decision

When you get enough practice under your belt as a creative professional, it’s likely that you will start getting more opportunities than you can handle.

It’s tempting to say yes as a knee-jerk reaction, but Epictetus teaches us the key to sound decisions:

Cultivate the habit of surveying and testing a prospective action before undertaking it. Before you proceed, step back and look at the big picture, lest you act rashly on raw impulse. Determine what happens first, consider what that leads to, and then act in accordance with what you’ve learned.

I’ve found that being slow to decide on big decisions (taking on new projects, making a career pivot, starting a business, investing large amounts of resources or energy) is generally sound. If I could do it again, I probably would have waited three to six more months before starting my first business to survey the opportunity before going all in.

Not all bad decisions lead to failure. Some just lead to an addiction to small successes that lead to nowhere. Jim Harrison said, “A man can wear a corporate mask until he’s 55, retire early, then he finds that either he can’t take off the mask, or if he does, there’s no face under it.”

So, with every decision, slow down and ask, “Is this leading me where I want to go?”

Learn and Apply Your Knowledge

Applied knowledge is better than learning the textbook. Or, put another way, don’t settle for having only read the textbook.

Reading books on self-improvement, strategy, marketing, and peak performance helped me climb out of the mental ditch I’d fallen into after my business failed.

But at some point, I had to apply what I had learned in a manner that fit my work. Reading is an art that I deem as one of the most valuable things a human can do—but if we stop at reading, then we rob ourselves of the potential wisdom from applied knowledge.

Epictetus help me learn this when he said:

Don’t just say you have read books. Show that through them you have learned to think better, to be a more discriminating and reflective person. Books are the training weights of the mind. They are very helpful, but it would be a bad mistake to suppose that one has made progress simply by having internalized their contents.

Review Your Day (And My Suggested Review System)

In a letter to his older brother Novatus, Seneca describes a method he used to measure himself objectively. At the end of each day, he’d ask himself questions like: How am I better today? What did I do with my time? What were my outcomes?

I’ve iterated on this method and use a 5/3/1 system for review and planning.

I list the five must-dos for the next day, three things that went really well today, and one thing I am grateful for.

Here again is my entry from July 27, 2017:

This no-frills technique is a simple closing ritual for me at the end of each day. It leverages gratitude, productivity, and effective goal-setting.

The Solution Lies Within

If you really want to escape the things that harass you, what you’re needing is not to be in a different place but to be a different person. —Seneca

So many times, we want to run away, with hopes that the adversity will somehow disappear. I can report to you that this method is weak. It doesn’t work. And the Stoics knew that thousands of years ago.

There’s a time and place for divergence and escapism — vacation is the ultimate mental break. But resting is not the same as hiding. Avoiding your challenges often only intensifies the anxiety of facing up to the issue.

When my business failed, I fantasized about moving to another country.

Luckily, I had my wife to level me out. I had to learn so many things, like marketing, the growth mindset, branding, emotional intelligence, copywriting, deliberate practice, email etiquette, and the art of simply showing up. Moving wasn’t going to help with any of those.

The Importance of a Few Good Friends

We live in a time of scaled human connection — think Facebook, Twitter, even Medium. But how deep are these connections?

When something awful happens in your life, do you want an army of acquaintances, or would you rather have a friend in your corner who you’d trust to look after your kids?

The depth of a few good friendships is more important than a large quantity of acquaintances.

Here’s Seneca on friendship:

Think for a long time whether or not you should admit a given person to your friendship. But when you have decided to do so, welcome him heart and soul, and speak as unreservedly with him as you would with yourself. You should, I need hardly say, live in such a way that there is nothing which you could not as easily tell your enemy as keep to yourself; but seeing that certain matters do arise on which convention decrees silence, the things you should share with your friend are all your worries and deliberations.

and

Anyone thinking of his own interests and seeking out friendship with this in view is making a great mistake. Things will end as they began; he has secured a friend who is going to come to his aid if captivity threatens: at the first clank of a chain that friend will disappear. These are what are commonly called fair-weather friendships. A person adopted as a friend for the sake of his usefulness will be cultivated only for so long as he is useful.

I leaned heavily on my wife, two friends, my brother, and my sister when I was wounded. Interestingly enough, none of them shouted at me with strategies or solutions. Rather, they just hung in there with me and didn’t leave when I had nothing.

In the Stoic view, bad things happen, and you need to be prepared. The good things in my life are very much a result of being able to deal with the bad things. I hope that building your own resilience will have the same result for you.