209. Breaking the Rules of Philosophy

209. Breaking the Rules of Philosophy

Author: Nick Jamell April 2, 2021 Duration: 17:30

I once heard a teacher tell his students, "If you want to be able to break the rules, you have to know them first." Basically, the point is something similar to Chesterton's fence. Rather than breaking the rules when you don't understand them, you should only remove barriers with a good cause. In Meditations on First Philosophy, Rene Descartes flips the rules of philosophy on their head in this experiment.

"If you would be a real seeker after truth, it is necessary that at least once in your life you doubt, as far as possible, all things."

Rene Descartes

Know the Rules

Philosophy operates on certain rules and conditions, and it takes a lot to learn them. While I'm no expert, I do think that I know what I don't know. I enjoy philosophy and walking through arguments, but I don't have all the terms and processes down. But, I do see why the rules are in place. They keep the conversation on track and help people know how to "play the game." If two people want to spar or square off, the rules must be established and agreed upon. The framework philosophers have created over the last couple thousand years help us do that in a much more productive way.

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Different Ways of Breaking the Rules

Now that we know why we have the rules, I want to discuss the ways we break them. Rules can be broken out of ignorance, anger, spite, or for a good cause. So, it's important to know which reason you have to break a rule when you do it.

Here are some different ways people go about it:

  • Know the rules, and not care that you're breaking the rules
  • Not know you're breaking the rules
  • Know what the rules are and break them for a good reason
  • Break rules in play or in an exercise, but still abide by them

Watch or listen and find more content here --> Breaking the Rules of Philosophy show notes 


Nick Jamell hosts Conversation of Our Generation, a space where urgent contemporary questions meet enduring ideas from history and philosophy. Rather than reacting to the noise of daily headlines, this podcast deliberately steps back to examine the deeper currents shaping our society and culture. Each episode is a long-form dialogue that treats topics like politics, religion, and social change not as fodder for debate, but as puzzles to be understood with patience and intellectual humility. The aim is to move beneath entrenched partisanship and surface-level takes, searching instead for clearer perspectives and foundational truths. What you’ll hear are thoughtful explorations that connect modern dilemmas to the wisdom of ancient and modern thinkers, asking how we might navigate today’s complexities with a more grounded sense of principle. This isn’t about quick answers; it’s about cultivating a more meaningful and less reactive way of engaging with the world. For anyone feeling adrift in a polarized age, this podcast offers a sustained, earnest conversation that values depth over speed, and understanding over winning an argument. Tune in for a respite from the frantic news cycle and a chance to consider what it means to be part of this particular moment in time, armed with the best ideas from across the ages.
Author: Language: English Episodes: 245

Conversation of Our Generation
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