False Progress, Stoic Luck, and the Danger of Things Going Well
Episode #371
“Show me that you have your principles in order, not that fortune is currently favoring you.”
— Epictetus
As we get older, life often improves in measurable ways—especially financially. Many of us accumulate more wealth over time, thanks to steady work, smart investing, or just surviving long enough to benefit from compounding returns.
You could draw a line between age and net worth and see an upward slope. It’s comforting. Encouraging, even.
But here’s the Stoic problem: if you’re practicing detachment from wealth while your wealth is rising, how do you know if you’re actually growing?
Are you cultivating virtue and inner freedom—or just benefiting from fewer reasons to worry?
Premium subscribers will receive a new Stoic story later this week — a personal lesson about ego and a rental car. Stay tuned.
The Illusion of Progress
Stoicism teaches us to focus on what’s in our control: our thoughts, our actions, our responses. But when life is going well—when the stock market is up, your relationships are stable, and you’re sleeping well—it’s easy to feel like you’re making progress.
The truth? That might be false progress.
The Stoics might have called it progress in externals—things outside your control that happen to be aligned with your goals. You feel calm, not because you’ve mastered your reactions, but because nothing’s currently testing them.
That’s not philosophical development. That’s luck.
What Real Progress Looks Like
Real Stoic progress isn’t about how you feel when life is good. It’s about how you behave when life isn’t.
It’s about applying the dichotomy of control, staying steady in discomfort, and maintaining your character when it would be easier to abandon it.
“No man is more unhappy than he who never faces adversity. For he is not permitted to prove himself.”
— Seneca
That’s the benchmark. Not your net worth. Not your level of comfort. But how you respond when something important is taken away.
The Comfort Trap
If you’re wealthy and claim detachment, that’s great. But don’t confuse a lack of financial stress with genuine Stoic discipline.
True detachment only becomes visible in its absence. Only when something you value is lost—or threatened—do you find out whether you were truly free from it.
To be clear: comfort isn’t bad. Fortune’s gifts—wealth, love, ease—are to be appreciated. But they can’t be trusted as measures of your growth. They might just be softening the path rather than sharpening your skill.
Stoic Luck vs. Stoic Strength
Sometimes life just lines up: a promotion, a chance encounter, a new relationship right when you needed one. These are examples of what we might call Stoic luck—fortuitous external events that, if we’re not careful, we might confuse for signs of inner transformation.
Gratitude is appropriate. Complacency is not.
Because when things fall apart—and they eventually do—you’ll want more than luck. You’ll want the kind of strength that’s forged through friction.
The Real Metric of Progress
Here’s one way to think about philosophical growth:
You have a finite number of minutes in a day. In some of those minutes, you act appropriately—calm, virtuous, aligned with reason. In others, you don’t.
The Stoic path is simply about increasing the percentage of those minutes over time.
Some days will be better. Some will be worse. But over weeks, months, and years, the trend should be upward.
Progress, then, isn’t about reaching a fixed goal—it’s about trending toward wisdom. Steadily. Quietly. Relentlessly.
The Question to Ask Yourself
So here’s the reflection I’ll leave you with:
Is your current sense of peace coming from philosophical clarity—or from favorable conditions?
When you feel detached, when you feel strong, when you feel centered—ask yourself: Would I still feel this way if I lost something tomorrow?
Because if the answer is no, it might not be progress. It might just be the absence of pain.
And if that’s the case, you’re not behind. You’re not doing it wrong. You’re just being given a gentle reminder—by fortune or by philosophy—that you have more work to do.
We all do.
—
🧘♂️ Stay strong. Stay steady. And may your principles hold—especially when fortune doesn’t.
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Couldn't agree more.