A Stoic Conversation with Massimo Pigliucci: How to Be a (Happy) Skeptic

What does it mean to hold a philosophy of life with conviction but without certainty? That is the central question Massimo Pigliucci has been working on for years, and it is the question at the heart of his new book, How to Be a Happy Skeptic. This conversation is a direct continuation of that book and our encounters in Athens and Turin. We talked about Cicero, doubt, the difference between Stoicism and skepticism, and what it actually means to build a philosophical life that keeps examining itself.

Massimo Pigliucci is a professor of philosophy at the City College of New York, an evolutionary biologist turned philosopher, and the author of several books that have shaped how many of us first encountered Stoicism seriously. If How to Be a Stoic was an invitation to start, and Beyond Stoicism was an invitation to look wider, How to Be a Happy Skeptic is an invitation to look more carefully at what we think we already know.

Why Every Philosophy of Life Needs a Skeptical Check

Massimo’s philosophical journey did not start with Stoicism. He grew up Catholic in Rome, then moved through secular humanism, then into virtue ethics broadly, and eventually settled into Stoicism as the framework that resonated most with who he is. But the journey did not stop there. He noticed something that can happen to anyone who finds a philosophy that works: the temptation to stop asking questions about it.

Skepticism, in Massimo’s hands, is the tool that prevents that. Not a passive doubt, not a refusal to commit, but an ongoing willingness to examine what we believe and hold it with appropriate confidence rather than false certainty. Every statement about how to live, including Stoic ones, comes with the possibility of being wrong. The honest philosophical response is to acknowledge that rather than paper over it.

This is also why Massimo writes. Not to deliver conclusions, but to think things through more carefully. His books, his Substack (Figs in Winter), and his teaching all serve the same function: forcing himself to examine what he actually thinks and putting it out there so others can help him question it. That posture, of genuine inquiry rather than settled authority, is part of what makes the conversation we had on the podcast worth listening to.

The Three Ingredients of a Philosophy of Life

One of the clearest things Massimo offers in this conversation is a framework for understanding what a philosophy of life actually consists of. He identifies three components that appear in almost every serious philosophy, including religious ones: a metaphysics, an ethics, and a set of practices.

The metaphysics is the picture of how the world works. For the Stoics, the world is a chain of cause and effect governed by the logos, a rational order that connects everything. The ethics is the answer to what we should do within that world, for Stoics, living according to nature, cultivating virtue, acting as responsibly toward others as possible. And the practices are the daily habits that turn those principles into actual behaviour: journaling, reflection, the cardinal virtues in action.

What Massimo points out is that everybody already has all three of these, whether they know it or not. We all have some picture of how the world works, some sense of what we should do, and some habits that express those values in daily life. The question is not whether you have a philosophy of life. It is whether you have examined it.

Virtue Ethics: The Common Ground Between Stoics and Skeptics

A natural question in the conversation is how skepticism and Stoicism relate to each other. Were they rivals in the ancient world? Competitors? Massimo draws a helpful distinction. The Stoics and Epicureans disagreed fundamentally on the most important question of what constitutes the highest good in life. That was a real and significant rivalry. The Stoics and the academic skeptics, by contrast, were more like in-house critics. They agreed that arete, virtue and excellence of character, was the central good. Their disagreement was epistemological: could the sage have certainty, or only probability?

Carneades, the great academic skeptic, argued that even the wisest human reasoner remains fallible. Our senses can deceive us, our reason can mislead us, and we do not always know when either is happening. The Stoic sage may be less likely to go wrong, but he is not exempt from the possibility. What Carneades offered instead was a sliding scale of persuasiveness: some impressions are barely convincing, others are very strong, and we should act in proportion to how strong the evidence is. This idea, that belief should be proportioned to evidence, eventually became the foundation of probability theory when Cicero translated the Greek word pitanon as probabilis.

For Massimo, this is not a reason to abandon Stoicism. It is a reason to hold it more carefully, with an ongoing awareness that what we think we know, including what we know about how to live, is always provisional. The combination of Stoic ethics with academic skepticism is what he calls being a skeptical Stoic, or, as the title has it, a happy skeptic.

Cicero: The Relatable Philosopher Who Kept Going

The central figure of How to Be a Happy Skeptic is Cicero, and Massimo’s account of why he chose him has a compelling background. Cicero is not a sage. He did not have a perfect life or perfect equanimity. He was exiled, brought back in triumph, exiled again, lost his daughter to childbirth, saw his country fall into civil war, and at the end was hunted by soldiers sent by Mark Antony.

What makes him interesting is not that he handled all of this perfectly. It is that he kept going. In the years when his career was destroyed and his daughter had died, he wrote some of the most important philosophical texts in the Latin tradition. Not because things were fine, but because philosophy was what he turned to when they were not. And at the end, facing the soldiers, he asked them to cut his head properly. That is not the behaviour of someone who had conquered fear. It is the behaviour of someone who had worked with it long enough to act well in spite of it.

Massimo also points out that Cicero has been continuously influential for two thousand years, through the early Christian fathers, the Renaissance, the Enlightenment, and the American founding fathers. He has never gone away. And yet most people who are interested in Stoicism have barely scratched the surface of his writing. This book is partly an invitation to remedy that.

What This Means for How We Practice Stoicism Today

The practical implication of everything Massimo argues is not that we should stop being Stoics. It is that we should be Stoics with more intellectual humility: checking our beliefs regularly, asking where they came from, being genuinely open to revising them when the evidence points somewhere different.

This connects directly to the Stoic concept of eudaimonia, the flourishing that comes from living well and thinking well. How to Be a Happy Skeptic argues that genuine flourishing requires ongoing inquiry, not the comfortable settling into a system that tells you how to live without asking you to keep checking whether it is right.

The Stoics themselves understood this. Epictetus insisted that the first act of philosophy is to question which of our beliefs are actually ours. Marcus Aurelius kept returning to the same questions throughout the Meditations, not because he had not answered them before, but because he knew they needed to keep being asked. Massimo is working in the same tradition, just with a more explicit acknowledgment of the fallibility that was always part of the picture.

If you have read Beyond Stoicism and found yourself curious about what comes after exploring multiple philosophical traditions, this is the natural next step. It does not give you a new system. It gives you a better way of holding the one you have.

Frequently Asked Questions

What is a skeptical Stoic?

A skeptical Stoic is someone who accepts the core of Stoic ethics, that virtue is the highest good and that we should live in accordance with reason and nature, while also holding those commitments with intellectual humility rather than dogmatic certainty. The skeptical element comes from the academic skeptics of ancient Rome, particularly Carneades and Cicero, who argued that human knowledge is always probabilistic rather than certain. A skeptical Stoic acts on their best current understanding while remaining genuinely open to revising it.

What is the difference between Stoicism and skepticism?

Stoicism is a complete philosophy of life built around virtue, reason, and living in accordance with nature. Academic skepticism, as practiced by Cicero, is primarily an epistemological approach: a method for examining beliefs and holding them in proportion to the evidence. The two are not mutually exclusive. The ancient academic skeptics and the Stoics largely agreed on ethics, their disagreement was about whether certainty was possible. Massimo Pigliucci argues that combining Stoic ethics with skeptical epistemology produces a more honest and more durable philosophy of life.

Why is Cicero important for Stoicism?

Cicero is one of the most important sources for what we know about Stoic philosophy. Although he considered himself a Platonist, he drew heavily on Stoic ethics and preserved many Stoic arguments in his philosophical works. He was also the first to translate Greek philosophical terms into Latin, including the word probabilis from the Greek pitanon, which gave us the modern concept of probability. For anyone interested in Stoicism and Roman philosophy, Cicero is essential reading.

What does it mean to have a philosophy of life?

According to Massimo Pigliucci, a philosophy of life has three components: a metaphysics (a general picture of how the world works), an ethics (a sense of what you should do within that world), and a set of practices (daily habits that put those values into action). Everyone already has all three, whether they have examined them or not. The value of consciously developing a philosophy of life is that it gives you a framework for navigating difficulty, making decisions, and understanding what actually matters to you.

Is Stoicism compatible with doubt and uncertainty?

Yes, and arguably it requires it. The Stoics themselves placed enormous emphasis on examining impressions carefully before assenting to them. Epictetus’s instruction to pause before acting on any impression is itself a skeptical practice. What Massimo adds is an explicit acknowledgment that even our best philosophical commitments are held provisionally, that holding Stoicism with certainty is actually a departure from the careful reasoning Stoicism recommends. Doubt, in this sense, is not the opposite of Stoic practice. It is part of it.

Keep Asking the Questions

What stays with me from this conversation is something Massimo says almost in passing: that a philosophy of life is not something you arrive at and then rest in. It is something you keep examining. Cicero kept examining his until the very end, and the works he produced in his most difficult years are among the most enduring in Western philosophy. Not because he had found certainty, but because he had found a method for living with uncertainty well.

That is what being a happy skeptic means. Not the absence of conviction, but the refusal to let conviction become complacency.

Watch the full conversation on YouTube, or listen on Spotify and Apple Podcasts.

Want to Learn More?

If this resonated and you are ready to start building your own philosophy of life, a conversation with Benny as your Stoic coach can be a good place to begin. Not to be told what to think, but to have the space to figure it out. You can also sign up for the newsletter, The Pause, or watch or listen to the Via Stoica Podcast on YouTube, Spotify, or Apple Podcasts.

About the Author

Benny Voncken is the founder of Via Stoica and host of the Via Stoica Podcast. He has practiced Stoicism as a way of life for over six years, spoken at Stoicon, and led Stoic walks across Europe. Through Stoic coaching, he helps people use Stoic principles and practices to develop their own philosophy of life: one that gives them the tools to face obstacles, navigate change, and find more balance and peace. He writes, teaches, and walks wherever the philosophy takes him.