Living Deliberately: A Playful Dive into Stoic Life Rules (With Real-World Twists)

There’s a pile of unfolded laundry calling from the corner, half-written to-do lists scattered on the desk, and a gentle hum of existential dread in your mind. What does it *really* mean to live intentionally? That question hit me not during some mountain-top epiphany, but while microwaving cold coffee for the second (okay, third) time this morning. Instead of searching for mystical answers, I stumbled across an ancient guide—Stoic philosophy—and it turned out to be refreshingly down-to-earth. Let’s break down what the Stoics had to say about living a good life, one very human imperfection at a time.

The ‘Preferred Indifferents’ Dilemma: Wisdom’s Odd Sorting Game

In the ancient guidebook of Stoic philosophy, wisdom isn’t just about knowing a lot or being clever. It’s about sorting life’s endless stream of stuff into three buckets: good, bad, and—perhaps most confusingly—indifferent. This odd sorting game is at the heart of living a good life with intention and peace. As one Stoic-inspired voice puts it:

“Wisdom is about recognizing the difference between the stuff that is good, the stuff that is not good, and the stuff that is indifferent.”

How Stoics Categorize Life’s Stuff: Good, Bad, and ‘Meh’

Let’s break down the Stoic system:

• Good: Living virtuously, being kind, honest, and fair. These are always worth pursuing.
• Bad: Lying, greed, cruelty—think of the classic “seven deadly sins.” These are always to be avoided.
• Indifferent: Everything else. Money, career success, possessions, even whether someone texts you back. These aren’t bad, but they aren’t good in themselves either.

But here’s the twist: Stoics called some of these ‘indifferents’ preferred indifferents. They’re nice to have—like a winning lottery ticket or a viral YouTube video—but they’re not essential for a good life. You can prefer them, but your happiness shouldn’t depend on them.

Why Money, Success, and Love Aren’t the Endgame

Modern life is a parade of metrics: bank balances, follower counts, relationship statuses. It’s easy to obsess over these, thinking they’re the keys to happiness. But Stoic wisdom says otherwise. Money and success are preferred indifferents: useful, but not the foundation of a meaningful life. Even love, as vital as it feels, falls into this category. The Stoics didn’t say these things are bad—they just aren’t the ultimate goal.

Anecdote: The YouTube Subscriber Spiral and the ‘Voice of Derren Brown’

Imagine someone refreshing their YouTube analytics, watching the subscriber count tick up (or down). The excitement, the anxiety—it’s real. But then, the ‘voice of Derren Brown’ (the magician and Stoic enthusiast) pops up in their mind: “This is a preferred indifferent.” Sure, more subscribers are nice. But wisdom means not letting that number define your worth or peace of mind.

Wild Card: Serenity Prayer Remix & the Indifferent Lottery Ticket

The Serenity Prayer, a staple of Stoic-adjacent wisdom, goes:

“Grant me the serenity to accept what I cannot change, courage to change what I can, and wisdom to know the difference.”

In the Stoic remix, wisdom is the superpower that helps you sort your life into what matters and what doesn’t. Winning the lottery? Preferred indifferent. It’s fun, but it doesn’t touch your core character or virtue.

Most of what we chase—money, status, likes—is actually indifferent to whether we live a good life. Recognizing this, and focusing on what we can control, is the ancient guide to peace and intention. That’s the odd, liberating sorting game of Stoic wisdom.

Productivity vs. Procrastination: Temperance and the Illusion of ‘Getting It All Done’

Temperance as Self-Control: Why Binge-Watching Feels Good Yet Empty

Stoic philosophy teaches that temperance—the art of moderation and self-control—is key to a good life. It’s about balancing short-term pleasures with what’s truly good for us in the long run. Picture this: four hours lost to binge-watching Netflix or gaming. In the moment, it’s fun and easy. But as one Stoic-in-training put it,

'If I binge-play World of Warcraft for four hours, it feels good... but then afterwards I always have that nagging sense of, that wasn’t really that satisfying.'

The Diary of a Habitual Over-Planner: Lake District Trip Edition

Temperance isn’t just about resisting temptations like snacks or screens. It’s also about balancing life when it comes to work and self-improvement. Take the case of the over-planner heading to the Lake District with friends. Instead of relaxing, their mind races: “If I wake up before everyone else, I can squeeze in a few hours of writing before the hike.” The urge to always be productive—even on vacation—shows how self-discipline can go too far. True self-care strategies sometimes mean letting go of the to-do list and simply enjoying the moment.

Sometimes the ‘Productive’ Choice is to Take a Nap (Yes, Really)

Modern productivity tips often focus on doing more, faster. But sustainable productivity, according to research, comes from balancing effort with rest. Building positive habits slowly is more effective for long-term well-being than relentless hustle. Sometimes, the most productive thing you can do is take a nap, go for a walk, or just be present with friends. Temperance means knowing when to push forward—and when to pause.

Wild Card: Guitar-String Blisters and the Accidental Virtue of Moderation

There’s a quiet joy in choosing slow, meaningful progress over quick fixes. Imagine spending three hours learning a new song on the guitar. Your fingers ache, the chords don’t sound right at first, but by the end, you feel a deep sense of accomplishment. Compare that to four hours of mindless scrolling or gaming. The difference? One brings lasting satisfaction, the other leaves you restless. This is the accidental virtue of moderation: self-improvement that feels good not just now, but later too.

In the end, temperance is a surprisingly difficult balancing act. It asks us to moderate not just our pleasures, but even our drive to improve. The illusion of ‘getting it all done’ fades when we realize that a balanced life is built on both effort and ease.

Courage & Justice: Feeling the Fear, Doing the (Uncomfortable) Good

In the world of Stoic philosophy, courage and justice aren’t just grand ideas—they’re daily practices that shape a good life. The Stoics, and modern interpreters like Ryan Holiday and William Irvine, remind us that courage doesn’t cancel fear. Instead, it means feeling fear, anxiety, or discomfort—and acting rightly anyway. As one Stoic-inspired leader put it,

“When I feel fear, that’s usually when I should lean into doing the thing that I’m scared of.”

Courage: Butterflies Included

Take the story of launching a new business project. Before opening the doors to his online course, the founder felt a wave of fear: What if no one signs up? What if it flops? What if I’m out of my depth? Instead of waiting for those butterflies to disappear, he recognized them as a signal to act. That’s the Stoic way—leaning into fear, not away from it. This is resilience building in action: each uncomfortable step forward is a chance to grow.

But courage isn’t just for big launches. As his team grew to 10, new fears crept in—awkward salary talks, performance reviews, and tough feedback sessions. He admits, “I often shy away from difficult conversations because of this feeling of fear.” Yet, every mentor echoed the same advice: feel the fear and have the conversation anyway. Courage, in this sense, is personal responsibility—choosing to act by your values, even when it’s uncomfortable.

Justice: More Than Courtroom Drama

For the Stoics, justice goes beyond legal systems. It’s about community service, fairness, and doing right by others—even when it costs you. Justice is a duty to society, a call to act for the greater good. Sometimes, that means making hard choices that don’t benefit you directly.

Here’s a real-world twist: After running a paid membership community for alumni, the team noticed attendance dropping and value slipping. The easy path? Keep the money and hope things improve. The Stoic path? Cancel the membership, refund everyone—about $100,000 in total—and give the last six months of benefits for free. As the founder reflected,

“It was fine because it was like doing the right thing—and it was tied in with the Stoicism stuff.”

Growth in the Discomfort Zone

Imagine a day without any difficult conversations or scary decisions. Would anyone actually grow? The Stoics would say no. Leaning into fear and discomfort is essential for both personal and ethical growth. Courage and justice, then, are not just virtues—they’re the building blocks of a resilient, meaningful life. They ask us to act our values, serve our communities, and do the right thing, even when it’s hard.

• Courage: Acting rightly despite anxiety or fear—not waiting for the butterflies to disappear.
• Justice: Serving others and the community, even when it means financial or emotional sacrifice.
• Personal responsibility: Facing tough conversations and decisions for the greater good.

Conclusion: The Messy Art of Living Intentionally (You’re Already Doing It)

Living deliberately isn’t about having every answer, or following a perfect blueprint for the good life. In fact, the real art of living intentionally is a bit messy—full of trial, error, and the occasional laugh at our own stumbles. As one wise voice put it,

“I haven’t figured out this concept of how to live intentionally, but I’ve found that reading books specifically about Stoicism has really helped.”

That’s the heart of Stoic practices: not grand, heroic gestures, but small, daily habits and mindful choices. It’s about pausing to reflect, asking ourselves what really matters, and gently steering our actions in that direction. Even when we fall short (and we all do), the point isn’t perfection. It’s progress. It’s showing up, trying again, and learning to smile at the chaos.

For those seeking a little more guidance, ancient wisdom is never far away. Books like A Guide to The Good Life by William Irvine, Happy by Derren Brown, and The Obstacle Is the Way by Ryan Holiday offer practical insights that make Stoic life rules accessible for modern readers. Each of these books brings Stoic philosophy down to earth, showing how self-improvement and a positive mindset can be woven into our daily routines. Whether you’re drawn to Irvine’s clear guidance, Brown’s thoughtful reflections, or Holiday’s straightforward approach, you’ll find that Stoic principles are less about rigid rules and more about mindful practice.

Mindfulness practice and intentional reflection are two of the most accessible ways to bring Stoic wisdom into your life. You don’t need to meditate on a mountaintop or recite ancient texts by heart. Instead, you can start by noticing your thoughts, questioning your reactions, and choosing your next step with a little more care. These tiny moments of awareness—choosing gratitude, reframing setbacks, or simply pausing before you respond—are where Stoicism truly comes alive.

There’s no final exam in this journey. No one is keeping score. Living intentionally is about making the best choices you can, in the moment you’re in, and finding meaning in the ordinary. The ancient art of Stoic practices is about aligning your actions with your values, even when life feels unpredictable. It’s about accepting imperfection, getting up when you fall, and laughing at the mess along the way.

So, if you ever feel lost or unsure, remember: you’re already practicing the messy art of living intentionally, simply by caring enough to try. Let Stoic life rules be your compass, not your cage. Read, reflect, experiment, and above all, be kind to yourself. The good life isn’t a destination—it’s a direction, shaped by daily habits, a positive mindset, and the courage to begin again, every single day.