I didn’t find Stoicism during a crisis.

I found it during a slow pile-up. My mom had passed away about a year before, and I’d internalized the grief — pushed it down, kept moving. Before that, I’d come out of a long-term relationship. Moved countries. Started a new role. I was trying to learn a new language. None of it was falling apart. Everything was just… heavy.

I’d been following Ryan Holiday for a few years already. As a marketer, I naturally landed on his stuff. And then he wrote The Obstacle Is the Way. That book landed me directly into Marcus Aurelius and Meditations.

One line from Holiday helped rewire how I was processing all of the “heavy”:

“There is no good or bad without us; there is only perception. There is the event itself and the story we tell ourselves about what it means.”

The grief, the transition, the uncertainty — those were events. The weight I was carrying? That came from the story I was telling myself about them.

(* just a side note that Viktor Frankl says something almost identical in his classic Man’s Search for Meaning.)

The Obstacle Is the Way is probably the book I’ve gifted the most. And I think the reason is simple: most people don’t find Stoicism through a philosophy class. They find it sideways — through a podcast, a book recommendation, someone they already follow. And they almost always find it when they need it.

If you’re leading right now, you’re in a pile-up too.

Economic uncertainty. AI reshaping entire industries overnight. Political instability. Market shifts that nobody saw coming. The volume of decisions you’re making has compounded, and the clarity you have for making them hasn’t kept pace. You’re not leading in calm waters. You’re leading in chaos — and the chaos (unfortunately) isn’t temporary.

That’s exactly when this 2,000-year-old operating system becomes the most useful tool you own.

Why Stoic Leadership Is Misunderstood (And Why CBT Proves It Works)

Say “Stoic” and most people picture someone cold, emotionless, white-knuckling through life. Suppressing feelings. Toughing it out.

That’s a big misread.

In reality, the philosophy is about seeing clearly so you can act decisively. The Stoics weren’t interested in suppression. They were obsessed with perception — understanding the difference between what’s happening and the story you’re layering on top of it. (I’ve written before about why clarity beats confidence for leaders — this is the same principle at a deeper level.)

A fun and surprising fact for you. The most effective therapeutic framework in modern psychology was built directly on Stoic philosophy. Cognitive Behavioral Therapy — the gold standard for treating anxiety and depression — traces its roots straight back to the Stoics. Albert Ellis, who developed Rational Emotive Behavior Therapy in the 1950s, credited Epictetus as his direct inspiration. Aaron Beck, the founder of cognitive therapy, basically says the same thing. Every time a therapist teaches you to examine your thoughts, reframe your beliefs, or focus on what you can control — that’s Stoicism with a clinical wrapper.

Psychologist Julian Rotter’s research on locus of control reinforces the same idea from a different angle. People with an internal locus of control — those who believe their actions shape outcomes rather than external forces — consistently show better coping, lower perceived stress, and greater psychological adjustment. So what does that internal focus actually look like in practice? The Stoics had a name for it 2,000 years ago: the dichotomy of control.

So the practices work. There are 2,000 years of philosophical tradition and decades of clinical data saying so. The question is: why aren’t more leaders using them deliberately?

The Research Behind Stoic Leadership Practices

In 2024, Modern Stoicism ran its annual Stoic Week program — nearly 5,000 people signed up to practice structured Stoic exercises for about 40 minutes a day over seven days. They’ve reported results of vulnerability to depression decreased by 13.3%. Vulnerability to anxiety dropped 12.5%. Earlier years showed double-digit improvements in life satisfaction and flourishing. That’s one week of structured practice. No meds.

I’ve also personally done a few daily Stoic challenges that Ryan Holiday hosts, and I’ve always found them amazing resets.

And the people using these principles at the highest levels read like a leadership hall of fame. James Mattis, former Secretary of Defense, carried a tattered copy of Meditations on combat deployments — using it for perspective and emotional distance when the stakes couldn’t be higher. Tim Ferriss calls Stoicism his “operating system for decision-making” and popularized fear-setting, which is essentially a structured premeditatio malorum exercise. When Sports Illustrated profiled a number of NFL coaches, including Pete Carroll and Bill Belichick, they found that The Obstacle Is the Way had become a shared framework across professional sport.

And then there’s the original case study. Marcus Aurelius ran the Roman Empire for 19 years during a plague, frontier wars, and political instability. Historians still regard him as the paradigmatic philosopher-king. Edward Gibbon wrote that Marcus exercised “absolute power, under the guidance of wisdom and virtue.” His daily reflective writing became what we now call the book Meditations. These were the personal writings and thoughts of a man and were never intended for publication. It was his way of processing the world, his personal operating system for leading himself before leading anyone else.

The question isn’t whether Stoic practices work for leaders. It’s whether you have a system for using them.

The Stoic Leader’s Operating System: 5 Practices to Start This Week

Five practices to get started. Three are daily. One is weekly. One is on-demand.

Framing this as “five daily practices” undersells what actually happens. Starting will be the most difficult part of this. To get going, you might have to set a morning alarm, carry a notebook, or put a weekly review in your calendar. But at some point, maybe in a few weeks or a few months, you realize you’re not doing the exercises anymore. Because the ones that stick are ingrained, and you start thinking this way, you start operating with these lenses. And voila! You’ve built yourself a new default operating mode.

So here’s how to get started:

1. Morning Clarity Check

When you wake up and before the day starts, and the chaos of life slaps you in the face, ask yourself three questions: What’s in my control today? What isn’t? What’s the one action that matters most?

This comes from Marcus Aurelius’s morning journal practice, described in Meditations Book 2. He’d preview the day’s challenges and pre-decide his response before the chaos could dictate it for him.

You don’t have to believe the 2,000-year-old text, though; there’s modern evidence for why this works. Researchers Giada Di Stefano, Francesca Gino, Gary Pisano, and Bradley Staats ran a field experiment at Harvard Business School where employees who spent just 15 minutes reflecting at the end of each day improved their performance by 20–25% compared to those who spent the same time practicing. That simply translates to: thinking about your work beats doing more work. The morning version of this takes it one step further — you’re setting the frame before the day has a chance to set it for you.

2. Premeditatio Malorum: Rehearse the Worst to Lead Through It

Once a week, visualize the worst-case scenario for your biggest decision or project. Walk through it. How would you respond? What would you actually do?

Seneca, in his Letters from a Stoic, recommended this as deliberate mental rehearsal. The purpose isn’t pessimism — it’s preparedness. You don’t fear what you’ve already rehearsed.

And the psychology backs it up. Julie Norem and Nancy Cantor’s research on defensive pessimism found that anxious individuals who mentally rehearsed worst-case scenarios before a high-stakes task performed as well as or even better than their non-anxious peers. Meanwhile, those told to “think positive” actually performed worse. Gabriele Oettingen’s mental contrasting studies reinforced this from another angle — imagining a negative future and then grounding it in present capabilities produced significantly lower anxiety than either worry alone or baseless optimism.

Tim Ferriss on the other hand, turned this into a practical worksheet he calls fear-setting. Basically the same Stoic practice with modern packaging. The point is the same: walk through the worst so that if it arrives, you’ve already met it.

3. The Evening Audit: Three Questions to Close Every Day

At the end of each day, three questions: Where did I react instead of respond? Where did I waste energy on something I couldn’t control? What would I do differently?

This comes from Seneca’s evening practice. As he wrote in Moral Letters: “I will keep constant watch over myself and — most usefully — will put each day up for review.”

James Pennebaker’s expressive writing research found that this kind of reflection works at a physiological level. When people write about emotionally significant experiences for 15–20 minutes across several days, it reduces distress and improves both mental and physical health. The key finding from follow-up meta-analyses: the largest effects come from writing that combines emotion expression with meaning-making. That’s exactly what the evening audit does — you name the reaction, then reframe it. Process and learn in the same five minutes. (If you want to go deeper on how gratitude and reflection work together, I wrote about the gratitude paradox and why success without reflection feels hollow.)

4. Voluntary Discomfort: Choose the Hard Thing Before It Chooses You

Choose one hard thing this week that you’re avoiding. Ship the post. Have the conversation. Make the decision you’ve been sitting on.

Seneca recommended practicing poverty, going without, deliberately exposing yourself to what you fear — so that when real hardship arrives, you’ve already met it on your own terms.

The science behind this is called hormesis: the principle that exposure to mild stressors triggers adaptive responses that build resilience to bigger ones. A randomized controlled trial in the Netherlands (N=3,018 adults) found that finishing daily showers with 30–90 seconds of cold water reduced sickness absence by 29% over 3 months. (I’ve actually been finishing my showers cold for more than ten years. Before it became a thing. Did it reduce my sick time? I have no clue, but I do feel as if I’ve done a hard thing at the start of the day.) Military stress inoculation training uses the same principle at a higher intensity — progressive exposure to controlled stressors builds the capacity to perform under real pressure.

But cold showers aren’t really the point here. What matters is that leaders who practice discomfort by choice — hard conversations, shipping imperfect work, saying no when it’s easier to say yes — handle discomfort by circumstance better. Steven Pressfield calls the thing you’re avoiding Resistance. And Resistance is almost always the signal pointing toward growth.

5. Amor Fati Reset: Turn Setbacks Into Starting Lines

When things go wrong — and they will — ask one question: “This happened. What am I going to do with it?”

That’s amor fati in practice. The concept is ancient (Nietzsche named it, but the Stoics lived it), and Marcus Aurelius captured the essence in Meditations: “The impediment to action advances action. What stands in the way becomes the way.”

And Viktor Frankl, who survived Auschwitz and went on to write Man’s Search for Meaning, said that: “Forces beyond your control can take away everything you possess except one thing — your freedom to choose how you will respond to the situation.”

This isn’t positive thinking or denial. It’s using acceptance as the starting line for action. The event already happened, and your response is where your power lives. (I explored a similar idea through the lens of kintsugi in The Golden Repair Method — the Japanese art of repairing broken pottery with gold. Same principle: what breaks you can become what defines you.)

The Real Edge: From Practice to Operating System

The whole point of this is that stoicism tends to be a way of life. It might start off as a set of exercises after you read this article. You do the morning clarity check until you start simply asking yourself, “What’s in my control?” all the time. All without the prompt. Over time, the evening audit becomes part of your way of thinking and your life. Eventually, for every situation that pops up, you already run through the worst-case scenarios so that nothing surprises you, because you’ve already rehearsed them in your head.

That’s the real edge you gain here: not a morning or evening routine, but a change in your operating system that runs beneath every decision you make.

The Obstacle Is the Way didn’t give me answers during that pile-up of grief and transition. It gave me a framework for finding them. Every transition since, every hard decision, every moment where the ground shifted underneath me — the system holds. Not because it prevents problems. Because it changes how I see them. And life is very much about perspective.

That’s why it’s the book I’ve gifted the most. Not because it’s the smartest thing I’ve read. Because it’s been one of the most useful.

If you’re leading through uncertainty right now — and I’d bet you are — the question isn’t whether you need this. It’s whether you’ll start.

What’s one Stoic idea that’s already changed how you lead — even if you didn’t know it was Stoic when you found it?