You have rules about how life should work. Everyone does.
I should always be honest. Hard work always pays off. I need to be productive. If I rest, I'm lazy.
You probably couldn't list them all if I asked — most of them sit below the surface, running your decisions without your permission. But they're there. And some of them are making you miserable.
Socrates had a method for dragging these rules into the light and testing whether they actually hold up. It's called the two-column technique, and it's one of the simplest philosophical tools I've ever come across. It's also, I think, one of the most underrated.
The rule doesn't disappear. But it loosens. And that loosening is where wiser action becomes possible.
I interviewed Donald J. Robertson — Stoic author and cognitive behavioural therapist — about this method recently on the podcast. What struck me was how bluntly he put it: "Socrates didn't see wisdom as maxims you buy like onions from a grocer. It's a cognitive skill." Not a collection of right answers. A way of thinking.
That distinction matters more than it sounds like it should.
Where This Comes From
Socrates didn't write anything down. But his student Xenophon gives us a scene in Memorabilia (Book 4, Chapter 2) that reads like a philosophy tutorial caught on camera.
Socrates is in a saddlery in Athens, talking to a young man called Euthydemus — someone who's collected a library's worth of self-improvement scrolls and thinks he's figured out wisdom. Socrates sketches two columns: "Justice" on one side, "Injustice" on the other. He asks Euthydemus to sort actions — lying, stealing, deceiving — into the right column.
Easy enough. Lying is unjust. Obviously.
Then Socrates does what Socrates always does. He asks: "What about a general who lies to his enemy to win a battle? What about a parent who hides medicine in a child's food because the child refuses to take it?"
Euthydemus's neat categories fall apart. The exceptions pile up. The rigid rules he thought he understood turn out to be far more conditional than he realised.
That's the whole technique. Take a rule. Find the exceptions. Watch the rigidity dissolve.
Was Socrates doing this daily with a notebook? Almost certainly not — he was an oral philosopher, and this was probably scratched on a wax tablet to make a point. But the method itself is timeless. And it turns out to be remarkably close to something modern therapists use every day.
Why Rigid Rules Make You Miserable
If you've ever done cognitive behavioural therapy, the two-column method will look familiar. CBT therapists use almost exactly this structure — writing down a belief in one column and evidence against it in the other — to help people challenge the thoughts that drive their anxiety, anger, and depression.
That's not a coincidence. Robertson pointed out in our conversation that the founders of CBT, particularly Albert Ellis, were directly influenced by Stoic philosophy. The connection runs deep.
But you don't need a therapist to see the problem with rigid rules. You can feel it.
I must always be honest sounds noble until you realise that sometimes honesty is a weapon. Telling someone exactly what you think of their life choices — right now, while they're struggling — isn't virtue. It's cruelty with a philosophical alibi.
I should always say yes when people need help sounds generous until you're burning out, resentful, and no use to anyone — including yourself.
I need to be productive all the time sounds disciplined until you notice that the "rest" you keep refusing is the thing that would actually make your work good.
The rigidity is the problem, not the rules themselves. Every one of those beliefs contains something true. But applied without exceptions, they become traps. Robertson put it well: "Rigidity breeds anxiety. Exceptions set you free.
How I Actually Use This
I'll be honest — I didn't start using the two-column technique because I was interested in Socratic philosophy. I started because I caught myself spiralling over a decision I'd already made and couldn't undo.
The rule running in the background was something like: I should never make decisions that disappoint people. When I wrote that down and started listing exceptions, it took about thirty seconds to realise how absurd it was. Every significant decision I've ever made has disappointed someone. Moving countries. Changing careers. Saying no to things I didn't have capacity for. The exceptions weren't edge cases — they were my entire adult life.
Oh. So this rule has been running me, and it's wrong most of the time. Good to know.
That's the shift. Not from "I believe this" to "I don't believe this." From "I believe this absolutely" to "I believe this sometimes, and I need to think about when."
Here's how to do it yourself. It takes five minutes.
Pick a rule you live by. Something you'd defend if someone challenged it. "I shouldn't show weakness." "I need to have a plan." "Hard work always pays off." Write it down.
List every exception you can find. Situations where following this rule would backfire, hurt someone, or make things worse. Don't filter. Don't defend the rule. Just list.
Look at what the exceptions reveal. If you can list three or more genuine exceptions, the rule isn't a rule — it's a tendency. And tendencies can be adjusted. Ask yourself: Given these exceptions, how do I want to hold this belief going forward?
That's it. No app. No complicated framework. Just a pen, two columns, and the willingness to be honest with yourself.
The interesting thing is that when I do this regularly — even once a week, just picking whatever belief is causing friction — I make better decisions. Not because I've figured out the "right" rules, but because I've stopped treating any rule as if it can't be questioned.
Which, if you think about it, is exactly what Socrates was trying to teach Euthydemus in that saddlery.
The Connection to Stoic Practice
If you practise Stoicism, this method plugs directly into work you're probably already doing.
The Stoics argued that most of our suffering comes not from events themselves but from our judgments about events — the rigid interpretations we layer on top of experience. Epictetus opens the Enchiridion with precisely this point: it's not things that disturb us, but our opinions about things.
The two-column technique is a way of catching those opinions in the act. When you write down "I should always be in control" and then list all the situations where that belief causes you to grip tighter and feel worse, you're doing exactly what Epictetus recommended. You're examining your judgments. You're testing whether they hold.
Robertson made this connection explicit in our conversation. The Stoics didn't just want you to accept their teachings on faith. They wanted you to reason your way to wisdom — the same way Socrates did, by questioning, by looking for exceptions, by refusing to accept a belief just because it feels certain.
The two-column technique isn't a Stoic exercise. But it's a Socratic one. And Socratic questioning is the root system beneath everything the Stoics built.
There's something freeing about that. You don't need to memorise more philosophy. You need to get better at questioning the rules that are already running your life.
Try This Week
Pick one belief that's causing you friction right now. You'll know which one — it's the one connected to whatever's been keeping you up at night, or whatever argument you keep replaying.
Write it down. List the exceptions. See what loosens.
If you want, share what you found. I'm always curious which rules people discover they've been living by without realising it.
If this kind of structured practice appeals to you, the 7-Day Stoic Challenge walks you through one exercise per day for a week — including exercises that examine your judgments and assumptions. It's free, audio-based, and takes about ten minutes a day.
Already practising? The Stoic Vault gives you a new exercise every Monday, with coaching and a quiet community of people doing this work alongside you.
— Jon