Stepping Into Possibility
Ancient Stoic Wisdom for Modern Life, Work, & Relationships
This is a companion piece to my 30-minute presentation on Stoic philosophy.
CSA: This article is the inspiration for today’s 30-minute Monday on Purpose call at 11 a.m. ET. Click here for details, and hope to see you there!
stoicism is stupid
I mean it.
Lowercase-s stoicism — the common-usage version, the “keep a stiff upper lip,” the “push through and don’t feel anything” version — is a terrible strategy for building a life worth living.
Life is full of challenges, setbacks, and invitations for suffering. Grimly enduring them will bring you no peace, no prosperity, and no well-being. It just makes you tired and brittle.
But capital-S Stoicism? The ancient philosophy of life? That’s a different thing entirely.
Stoicism doesn’t ask you to stop feeling. It teaches you to stop allowing yourself to be hijacked by your feelings. It doesn’t ask you to endure life. It asks you to flourish in and through it in any circumstances.
For the past four decades, Stoic philosophy has been quietly running in the background of my life — shaping how I navigated a music career, how I run a business, how I handle failure, and how I try to show up as a husband, father, and grandfather.
I didn’t set out to become a student of Stoicism. It found me in a seventh-grade Latin class, and it never let go.
Here’s what I’ve learned.
How Marcus Aurelius Inspired a 12-Year-Old Kid
Beginning in the seventh grade, I started studying Latin with an extraordinary teacher named Don Kelly. In Don’s class, we translated passages from Meditations, written by Marcus Aurelius — the Roman Emperor — nearly two thousand years ago.
Marcus didn’t write Meditations for publication. They were private notes — reminders to himself about how to handle difficult people, how to stay focused on what matters, how not to let power or praise or fear corrupt him.
Meditations read less like a philosophy textbook and more like the journal of someone trying very hard to be a decent human being under extraordinary pressure.
Something about that grabbed me. I asked Don for more passages to translate. Instead, he lent me his personal copy of the book. I read it cover to cover, then read it again. I read it annually throughout high school, college, and beyond. At graduation, Don gave me the book as a gift.
Here’s the thing — I didn’t know I was reading Stoic philosophy. I didn’t know there was a name for what Marcus was doing. I just knew that this Roman emperor talked to himself the way I talked to myself. He pushed himself to become a better human being in the very way I wrote in my own journal.
It wasn’t until decades later that I understood what Marcus was drawing on — and how powerful it becomes when you use it with intention.
What Stoicism Actually Is (The Short Version)
Every ancient philosophy was trying to answer the same question: What does it mean to live a good life?
The Stoics had an answer, and they had a word for it: eudaimonia. It’s Greek, often translated as “happiness,” but that’s misleading. It doesn’t mean pleasure. It doesn’t mean comfort. It doesn’t mean getting everything you want.
It means flourishing. A consistent sense of well-being — not because everything is going your way, but because you’ve developed the character to navigate whatever comes.
How do you get there? The Stoics said: through excellence of character. They called it arete — virtue. Not virtue in the moralistic sense. Virtue as in becoming the best version of what a human being can be: clear-thinking, fair, brave, and self-governed.
They also said we should “live in accord with nature.” This doesn’t mean passivity or tree-hugging. It means living in line with what a human being actually is. We’re rational — we can think. We’re social — we need each other. We’re finite — our time runs out. And we’re responsible — we get to choose how we respond to what happens.
This philosophy was practiced by Marcus Aurelius, the emperor of Rome; Epictetus, a formerly enslaved man who became one of the great teachers of the ancient world; and Seneca, a statesman and writer who advised emperors. A philosophy that worked for slaves and emperors alike. That tells you something about Stoicism’s range.
Like what you’re reading? Please share it. People like us do things like this!
The One Sentence That Changes Everything
The most practically useful idea in all of Stoicism fits in one sentence.
Epictetus opened his Handbook with this:
“Some things are within our control, and some things are not.”
We don’t control events, outcomes, other people’s opinions, the economy, the weather, or the past. We do control how we see what’s happening, what we choose to do about it, and who we’re going to be in the process.
If you’ve heard the Serenity Prayer — “Grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference” — you’ve heard Epictetus in different clothes.
This sounds simple. It is simple. But it is not easy — because most of us spend enormous energy trying to control things that aren’t ours to control while neglecting the things that are.
Your Operating System: The Three Disciplines
Marcus Aurelius kept coming back to three practices — three disciplines — that the Stoics developed for putting the dichotomy of control to work in daily life. Think of these as an operating system for navigating anything life throws at you.
The Discipline of Perception
How you see what’s happening.
Not just what happened — but the story you tell yourself about it. Most of our suffering comes from the narrative, not the event. Someone cuts you off in traffic and suddenly you’re furious — not because of the car, but because of the story: “They don’t respect me. People are terrible. The world is getting worse.”
The discipline of perception asks you to strip the story away. See what’s actually happening. Then decide — deliberately, rationally — what it means.
The Discipline of Action
What you do next.
Not reacting from emotion. Not lashing out. Not withdrawing. Choosing a response aligned with who you want to be and that serves not just your interests but the common good. The Stoics were insistent: we are social creatures. Our actions are supposed to benefit others, not just ourselves.
The Discipline of Will
What you hold onto and what you release.
This is about accepting that you control the quality of your effort, not the outcome. You can prepare, aim true, give your best — and the result still isn’t entirely yours. The discipline of will is the practice of putting your heart into the work and then letting go of what happens next.
Marcus summed it up:
“All you need are these — certainty of judgment in the present moment; action for the common good in the present moment; and an attitude of gratitude in the present moment for anything that comes your way.”—Marcus Aurelius, Meditations
What Stoicism Doesn’t Mean
Here’s where people get confused.
When the Stoics said virtue is the only true good, they were not saying that health, money, relationships, and success don’t matter. Of course they matter. But they’re not all that matter and the definitely don’t matter above everything else.
The Stoics had a term for these things: preferred indifferents. Things genuinely worth pursuing — but that don’t determine whether you are a good person or whether your life is ultimately well-lived.
Think of it this way: pursue prosperity, absolutely. Build something meaningful. Take care of your health. Nurture your relationships. But hold all of it lightly. Don’t confuse having more with being better. And don’t let any of it become your master.
Money matters. Health matters. Relationships matter. Stoicism just refuses to let them own you.
The Three Questions: A Practical Framework
I’ve spent years teaching the three disciplines, and I’ve found that the simplest way to put them to work is with three questions.
1. “What’s now?”
This is the discipline of perception in action. When something happens — a setback, a surprise, an argument, a fear — before you do anything, zoom out. Name what’s actually happening in plain language. No drama. No adjectives. No catastrophizing. Six to ten words. Just the facts.
Let me give you an example.
I’ve been a freelancer for over thirty years. You only make money when you have a gig. Almost every day, I wake up and check my calendar. Sometimes I can tell I don’t have enough gigs to cover the bills.
On those mornings, here’s what happens inside my head:
“I don’t have enough gigs. No gigs, no money. I can’t pay the bills. What if I can’t pay the mortgage? My kids will hate me. My wife will leave me. I’ll end up living in a box under an overpass and die alone and hungry.”
I go there really quickly. And more often than you’d think.
But when I zoom out and state what’s actually happening — without the apocalypse — here’s what I get:
“I don’t have enough gigs on the calendar to pay my bills.”
Same situation. Completely different starting point. Now I can work the problem instead of letting the problem work me over.
2. “What’s next?”
This is the discipline of action. Once you’ve named reality clearly, list your options. Cross out anything that doesn’t align with your values or who you want to be. From what’s left, choose the step that moves you forward without causing harm.
In my case, I might reduce expenses. Connect with past clients for referrals. Raise my fees. Sell a couple of guitars I don’t play anymore. There are real options once the panic clears.
3. “What matters?”
This is the discipline of will. Before you act, check in: Am I being the person I want to be? Is this decision aligned with my values?
The Stoics believed the quality of your character is measured by the quality of your decisions, not by the outcomes you get. Outcomes aren’t in your control. But the integrity of how you show up? That’s always yours to own.
These three questions — What’s now? What’s next? What matters? — work for a business crisis, a family argument, a health scare, or just the question of what to do with your life. They scale.
The Archer and Amor Fati: Releasing Your Grip on Outcomes
“But I still need results.” I hear you. So let me share two ideas that changed how I think about outcomes.
The Archer
This metaphor comes from Cicero. Imagine an archer stepping onto the field. She notches her arrow, draws back the bowstring, and takes aim. What’s her goal?
Most people would say, “Hit the bullseye.”
But the wise archer sees it differently. Her goal is to put forth the best effort she’s capable of in that moment. She’s spent years training. She’s maintained her equipment with care. She’s taken care of her body and mind. She’s done everything within her power to be ready.
But a sudden wind could blow the arrow off target. A rival could bump the stand. The unexpected could intervene.
So when she releases the arrow, she releases her attachment and expectations about the outcome as well. If she hits the bullseye, she doesn’t puff up with pride. If she misses, she doesn’t collapse. She aimed true. She gave her best. That was the goal.
There’s a line from the Bhagavad Gita that says the same thing: “You are entitled to your labor, but not the fruits of your labor.”
The process is its own reward.
Amor Fati
The Stoics took this even further with a concept called amor fati — love of fate. And this is where Stoicism decisively separates itself from lowercase stoicism.
Amor fati doesn’t mean gritting your teeth and tolerating what happens. It means loving it. Welcoming it. Treating every setback, every surprise, every unwanted turn as a necessary part of the canvas of your life.
Not because you’re pretending everything is fine. But because you recognize that your growth, your character, your depth as a human being — all of it has been shaped by the difficult things as much as the good ones. Maybe more.
So what does amor fati look like in practice? Not just in the big moments, but in everyday life?
For years, when someone asks me “How are you?” or “How is everything?” I’ve answered the same way: “Perfect in every way.”
I’m not delusional. I know I’m not really perfect in every way, and neither is everything. But at the moment someone asks, I am who I am and where I am. I and my circumstances are “perfect in every way” simply because they are as they are.
And…
At that moment lies my opportunity — to frame myself and my situation in a way that creates worthwhile choices, to make an assertion about who I want to be and how I can make things better, and to choose my next best step forward into that possibility.
I’ll do all of that imperfectly. Everything will not turn out as planned. But everything will unfold as it should. And then I’ll find myself in a new moment, with a new opportunity to choose again.
I’ve been a freelancer all my life — as a musician, teacher, writer, coach, and community leader. I’ve failed or fallen short far more often than I’ve succeeded. Yet I’ve felt a sense of thriving every step of the way. “Perfect in every way” is amor fati made into a daily practice. It’s an attitude anyone can adopt.
Here’s the secret: when you release your grip on outcomes, your work gets better. You’re freer. More creative. More present. Less anxious. You aim true, you let the arrow fly, and you love whatever comes next.
“Isn’t That Interesting...?”
One last tool. Three words that have changed how I respond to almost everything.
The next time something goes sideways — at work, at home, in your own head — before you react, before you spiral, try saying:
“Isn’t that interesting...?”
“Isn’t” raises a question — you’re in inquiry mode now, not panic mode. “That” makes it specific — you’re looking at the thing, not drowning in it. “Interesting” engages curiosity.
And here’s the key: it is impossible to be anxious and curious at the same time. They can’t coexist. Curiosity crowds out panic.
The pause at the end — the “...?” — is where your rationality gets back in the driver’s seat. That’s where you remember you get to choose what happens next.
Try it this week. Just once.
You Already Have Everything You Need
Stoicism isn’t about becoming some emotionless sage. It’s not about pretending life doesn’t hurt. It’s about becoming more fully human. More present. More generous. More resilient. More honest about what you can and can’t control, and more committed to showing up with integrity regardless.
Stoicism is about flourishing in any situation, despite any circumstances, by exercising your agency over how you see things and what you decide and do next, without compromising who you are and who you seek to become.
You already possess everything you need. You are sufficient even as you strive.
You were born with the capacity for reason, a creative impulse, and a social instinct that connects you to every person you meet. The Stoics just gave us a framework for putting those gifts to better use.
This week, in a difficult moment — just one — try the three questions:
What’s now? What’s next? What matters?
And when the unexpected happens, try three words:
Isn’t that interesting...?
See what opens up in that space.
Keep Going
If this resonated, here’s where to go next:
Start reading the Stoics. Marcus Aurelius, Meditations (Gregory Hays translation) — the most accessible entry. You can open it to any page. Epictetus, The Art of Living (Sharon Lebell translation) — 93 short practices. Seneca, Letters from a Stoic — like getting advice from a sharp, thoughtful friend.
Book me to present a 30-minute Stoicism talk for your venue or group — in-person or online. Click here for details.
Go deeper into the three questions. My book Onward: Where Certainty Ends, Possibility Begins unpacks the three disciplines as a complete framework for navigating uncertainty.
Download the worksheet. A one-page version of the three-question framework you can print and put where you’ll actually see it.
Stay in the conversation. I write here every week about Stoicism, purposeful living, and the kind of work that makes a real difference. I’m glad you’re here.
Scott Perry is an art of living cornerman and Chief Difference-Maker at Creative on Purpose. He’s been studying and applying Stoic philosophy since discovering Marcus Aurelius’s Meditations in a seventh-grade Latin class. He is the author of Endeavor, Intrepid, and Onward, and writes weekly at Creative on Purpose on Substack.
Spread the Goodness! Tap the ‘Like’ button, leave a comment, and restack this post to help other purpose-driven difference makers collide with this content.
Embrace clarity, take intentional action, and let go of what doesn’t serve you. Subscribe now to start living on purpose, not get held back by perfection.
I needed to read this, now, today. Thank you for your words and prospective. They helped me more than you know.