The Endless “Why?” Why Radical Skepticism Isn’t a philosophical dead end but a powerful tool for clear thinking. What if the ultimate goal of philosophy isn’t to find final answers, but to ask better questions?
For over two millennia, radical skepticism—the relentless “why?” that leads to infinite regress—has been dismissed as either a childish game or an impractical barrier to progress. But this view mistakes its purpose. Rooted in Sextus Empiricus’s Pyrrhonism and echoing in Zhuangzi’s butterfly dream, this tradition doesn’t seek to paralyze thought. Instead, it exposes the unexamined foundations every discipline, including science and metaphysics, quietly rests upon.
Critics like Kant saw skeptics as “nomadic barbarians” threatening civilization’s intellectual achievements. Others, like Hume, argued we live by inductive faith, not certainty, making suspended judgment unrealistic. Heidegger added that skeptics wrongly elevate epistemology over practical life. Yet the Chinese philosopher Zhuangzi offers a different model: aware of the Zhuangzi-butterfly paradox, he doesn’t suspend judgment but moves through life with a healthy wariness of certainty. This suggests skepticism’s “impracticality” stems not from the doubt itself, but from prioritizing abstract theory over lived experience.
This cross-cultural lens reveals skepticism’s true strength: as a presuppositionless starting point. Without a fixed framework, the skeptic is uniquely equipped to uncover hidden assumptions in everyday reasoning and other fields. Consider thinkers who attacked metaphysics—A.J. Ayer’s verification principle or Richard Rorty’s critique of mirroring nature—who might have avoided foundational criticisms by embracing the infinite regress from the outset. The skeptic simply admits: “I stand on no final ground,” turning vulnerability into clarity.
Ultimately, radical skepticism liberates philosophy from the Enlightened demand for linear progress. If we let go of the need to “solve” doubt, we open space for ongoing, humble inquiry. The value isn’t in reaching a destination, but in continually examining the map. In a world awash with absolute claims, the ancient practice of questioning everything may be the most practical, and progressive, mindset of all.
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