Stoicism VS Skepticism
Which Ancient Philosophy Can Help Us Live Better Today?
Dear Classical Wisdom Reader,
We live in an age of information, of instant, accessible data reaching us from every corner of the planet, a remarkable feat unique to our modern age...
... and yet, amazingly, many of us feel less certain than ever.
Indeed, every day brings new reasons to question what we know, what we value, and how we ought to live. We are told to trust the experts, think for ourselves, pursue happiness, embrace uncertainty, cultivate resilience, challenge assumptions, and somehow make sense of it all.
It is no wonder that so many people find themselves searching for wisdom in a world overflowing with opinions. How can we, after all, distinguish what’s real and meaningful when there is so much noise?
Of course regular readers of this humble page will know that, despite the very modern technology, this is not the first time humanity has faced such questions.
More than two thousand years ago, philosophers in Greece and Rome wrestled with many of the same dilemmas that confront us today…
How do we know what is true? What should we believe when certainty is impossible?Can we live well amid political turmoil, social division, and personal loss?
Is happiness something we pursue...or something that emerges from living wisely?
These are the very questions that lie at the heart of our upcoming live event:
The Good Life: A Philosophical Face-Off on Stoicism, Skepticism, and How to Live
Wednesday, June 18th at 11:00 AM ET
At the center of the discussion is philosopher Massimo Pigliucci’s highly anticipated new book, How to Be a (Happy) Skeptic: The Power of Doubt in a Meaningful Life. Exploring the philosophy of Cicero, Massimo argues that skepticism, properly understood, is not cynicism or indecision.
Rather, it is an intellectual virtue... the willingness to question, inquire, and remain open-minded while still pursuing a meaningful life.
But, does Skepticism offer us the answers we are searching for?
We often imagine certainty as the goal. Yet history suggests that certainty can be dangerous, while thoughtful skepticism can be liberating. The challenge, of course, is determining where doubt ends and wisdom begins.
That is precisely what our panel will explore.
Joining Massimo Pigliucci will be two distinguished scholars whose work engages some of the most pressing philosophical questions of our time.
Vittorio Bufacchi, author of Why Cicero Matters, is one of today’s leading voices in political philosophy. His work on social justice, political violence, and human rights examines how philosophical ideas shape the societies we build...and the injustices we tolerate.
Robin Reames, author of The Ancient Art of Thinking for Yourself, studies ancient rhetoric and its remarkable relevance to modern life. In an era of polarization, misinformation, and increasingly fractured public discourse, her work asks how we can become better thinkers, better communicators, and more independent minds.
Together, Massimo, Robin and Vittorio will discuss…
…whether skepticism a path to wisdom...or a recipe for indecision?
…if Stoicism helps us better to navigate modern challenges?
…how should we think about truth in an age of competing narratives?
…what does it mean to live a good life?
And is happiness the goal...or is something deeper required?
Whether you are already fascinated by Stoicism, curious about Skepticism, or simply interested in living more thoughtfully, this discussion promises to challenge assumptions, spark new ideas, and offer practical insights for modern life.
After all, the ancient philosophers believed that philosophy was not merely something to study...it was something to practice.
Join us as we put that idea to the test. Make sure to register here:
Event Details
The Good Life:
A Philosophical Face-Off on Stoicism, Skepticism, and How to Live
Wednesday, June 18, 2025
11:00 AM Eastern Time
Live Online
Can’t attend live?
Register in advance and you’ll receive access to the full recording afterward, allowing you to watch at your convenience.
I hope you’ll join us for what promises to be a fascinating exploration of doubt, wisdom, happiness, and the art of living well…
All the best,
Anya Leonard
Founder and Director
Classical Wisdom