On Pleasure, Character, and Doubt: A Deep Dive into Beyond Stoicism

An interview with Massimo Pigliucci, Gregory Lopez, and Meredith Alexander Kunz

PAC would like to express their deepest thanks to Massimo Pigliucci. Gregory Lopez, and Meredith Alexander Kunz for this insightful look behind Beyond Stoicism: A Guide to the Good Life with Stoics, Skeptics, Epicureans, and Other Ancient Philosophers.

Massimo Pigliucci is an author, blogger, podcaster, as well as the K.D. Irani Professor of Philosophy at the City College of New York. His academic work is in evolutionary biology, philosophy of science, the nature of pseudoscience, and practical philosophy. Massimo publishes a regular column in Philosophy Now entitled “The Art of Living.” His books include How to Be a Stoic: Using Ancient Philosophy to Live a Modern Life (Basic Books) and Nonsense on Stilts: How to Tell Science from Bunk (University of Chicago Press). Massimo’s latest is Beyond Stoicism: A Guide to the Good Life with Stoics, Skeptics, Epicureans, and Other Ancient Philosophers (with Greg Lopez and Meredith Kunz, The Experiment). More by Massimo at figsinwinter.substack.com.

Gregory Lopez is the founder of NYC Stoics, co-founder and board member of The Stoic Fellowship, member of the Modern Stoicism team, co-host of Stoic Camp NY, and co-author of A Handbook for New Stoics (Live Like a Stoic in the UK) and Beyond Stoicism (Live Like A Philosopher in the UK). His main work is outside of Stoicism, where he is Research Lead for Examine.com and a contract researcher at Spark Wave. You can learn more and reach out at his personal website: greglopez.me.

Meredith Alexander Kunz is a writer and communications leader in Silicon Valley who creates compelling stories about complex ideas. Her work as Head of Communications and Engagement at Adobe Research focuses on computer science and innovative people who are changing the world with their discoveries. She writes and speaks on ethics and practical philosophy, with a special focus on how Stoic ideas can help us live better today. She created The Stoic Mom blog in 2016 to explore how Stoicism can help parents and kids. In 2025, she launched The Philosopher’s Compass podcast, sharing conversations about practical philosophy. She is also a Certified Professional Co-Active Coach (CPCC) and an ICF Associate Certified Coach, using an approach rooted in Stoic principles. She helps clients set meaningful goals and find inspiring ways to work towards them.

Tell us about Beyond Stoicism.

Out of all the Greco-Roman philosophies, Stoicism is probably the most popular right now. But just because it’s the most popular does not necessarily mean it’s the most useful for everybody! The goal of Beyond Stoicism is to make more people aware of the rich variety of practical life philosophies that came out of the ancient Greek and Roman worlds and help contemporary readers get a basic idea of how they can apply these philosophies to their contemporary lives.

In fact, Stoicism itself began as an eclectic philosophy of life, with its founder, Zeno of Citium, cobbling together ideas from Socrates, the Cynics, the Platonists, the Megarians, and others. In Beyond Stoicism we also discuss whether it is advisable to build one’s own philosophy from scratch and provide readers with tools sampled from the huge variety of Classical and Hellenistic philosophies.

As Seneca put it:

Shall I not follow in the footsteps of my predecessors? I shall indeed use the old road. But if I find one that makes a shorter cut and is smoother to travel, I shall open the new road. Men who have made these discoveries before us are not our masters, but our guides. Truth lies open for all; it has not yet been monopolized. And there is plenty of it left even for posterity to discover.

(Letter 33.11)

How did exploring Skepticism and Epicureanism for Beyond Stoicism ultimately enrich or refine your personal philosophy, Massimo?

Arguably the most surprising thing to emerge from the project for me was a new clarity about how to understand the Classical and Hellenistic philosophies we covered. Though I was aware of them individually, I hadn’t really thought much about how they were connected or differentiated. But then we came up with the three “ports” metaphor that provides the framework for the entire book, and that led me to a deeper appreciation of Greco-Roman thought.

As readers will see, we think that there were three major strands of Classical-Hellenistic philosophies: what we call the ports of pleasure, of character, and of doubt, which respectively correspond to philosophies that are centered on hedonism (Cyrenaicism, Epicureanism), on virtue (Platonism, Aristotelianism, Cynicism, and Stoicism), and on skepticism (Socraticism, Sophistry, Pyrrhonism, and Academic Skepticism). I hope others will benefit from the clarity that this way of looking at things brings.

As for the impact of Skepticism and Epicureanism on my conception of philosophy as a way of life, it has been enormous. While I ultimately reject Epicureanism, for instance, their tetrapharmakos, the four-fold “cure” for life, is very insightful, and so is their classification of human desires into natural and necessary, natural and unnecessary, and unnatural and unnecessary (hint: most people today make the mistake of going for the latter category). I also find myself in complete agreement with the Epicurean take on death and why we should strive not to be afraid of it.

Skepticism, especially in the form articulated by Academics like Carneades and Cicero, has been even more impactful on my personal philosophy, so much so that I consider myself a skeptical Stoic (with more than a dash of pessimism, but that’s another story). The Academic Skeptic notion that both our senses and our reason are fallible, and that therefore we ought to hold on to any particular belief as lightly as we can, always ready to change our mind if new information comes about, is very wise and very useful. That approach anticipates the dominant modern philosophical stances known as fallibilism and probabilism concerning truth, as well as Bayesian epistemology. Indeed, I got so much into this way of seeing things that my next book, out in June ‘26, is a philosophical biography of Cicero, entitled: “How to Be a (Happy) Skeptic: The Power of Doubt in a Meaningful Life–Lessons from Cicero’s Philosophy” (Penguin).

What was the criteria for selecting the thirteen ancient philosophers, Meredith, and what do you hope readers gain from this broader philosophical landscape?

We took a very broad look at Hellenistic philosophy, and we decided to cover the waterfront as much as we could in the format of an accessible, conversational book. We didn’t want to do a “survey” of all ancient thought, but instead, considered the relationships between thinkers and schools in Greece and Rome, and then used the three ports (pleasure, character, and doubt) as a way to organize this wide range of philosophers. At the launch of the project, we hadn’t thought to include the last section, “Here Be Dragons”... but as we worked on the chapters, we felt that we couldn’t write a Hellenistic philosophy book without saying something about Pythagoras, Stilpo the Megarian, and Hypatia. For me, this was an amazing opportunity to learn about some lesser-known philosophers I wasn’t really aware of at the start. Doing the research for this book was like earning another master’s degree!

Readers will encounter stories that they can relate to and likely know (like Aristotle’s effort to teach Alexander the Great as a young student), and some that will surprise them (like Pythagoras, who likely did not come up with the famous math theorem, and who thought he heard his friend’s voice coming from a dog’s bark). We also focused on specific moments from well known philosophers that you may not be familiar with, for example Plato’s attempt to create a philosopher-king in Syracuse. Readers will alsol have the chance to meet two women of ancient philosophical fame, Hipparchia and Hypatia. While Hypatia has been popularized by modern storytelling (in a recent film, and even TV appearances), few people know about Hipparchia’s quest to live a philosophical life as a woman and an ancient Cynic. To me, these stories are really inspiring.

And we can see ourselves and see our own questions represented in these philosophers’ stories and in their ideas, we (as readers and writers!) find new opportunities to explore how they could add to our own life philosophies. I personally learned much more about how I resonate with Academic Skepticism, and how I sometimes aspire to elements of Cynicism and Pyrrhonism and Epicureanism, even though I am unlikely to adopt those ways of thinking fully.

Which non-Stoic practical exercise did you, Gregory, find most immediately applicable to modern life, and why?

Perhaps the fourth exercise in the chapter on the Cyrenaics: trimming the excess.

Aristippus — the hedonistic founder of Cyrenaicism — claimed that insatiability was a key sign of someone who did not truly understand what was necessary to live a pleasant life. Trimming indulgences that don’t bring much additional pleasure on the margins was a key exercise in training the virtue of temperance and allowed Cyrenaics to jump off the hedonic treadmill of insatiability.

The thing I particularly like about this exercise is that it’s a great example of an exercise that can work across different philosophies. A Peripatetic may trim excesses in order to practice hitting the golden mean; a Stoic may perform this exercise to strengthen the virtue of temperance for its own sake; an Epicurean can practice trimming excess physical pleasures in order to improve mental tranquility. The steps one takes to trim the excess are the same for each philosophy; however, the reasons for performing the exercise — as well the mindset you bring to the exercise and things the practitioner tells themselves while practicing — can be quite different. Thus, trimming the excess is not only useful and simple (but not always easy) to do: it also is a great example of a practice that many schools of philosophy could perform in different ways.

Do you have a favorite quote?

Massimo:

We should not be too confident in our belief in anything.

Cicero, Tusculan Disputations, 1.32

This quote opens chapter 9, appropriately entitled “Embrace uncertainty.” It is so apt for the times we live in that it could have been written by a 21st century influencer. Arguably, a lot of the trouble with humanity derives from the fact that so many people are so damn sure of their beliefs, often on extremely flimsy bases. It’s not just that, as David Hume put it, a wise person ought to proportion their beliefs to the evidence; it’s that doing so makes us automatically more tolerant of other people’s beliefs, both because we understand that we could be wrong, and because we realize that if someone holds onto a belief we dislike that person may simply be ignorant, as Socrates put it, not evil. Skepticism, then, becomes a way to cultivate tolerance, one of the most crucial and yet elusive of human attitudes.

Gregory: A modification of the fourth piece of advice Marcus gives himself in Meditations 11.18. There, Marcus gives himself ten pieces of advice when dealing with people he finds difficult. In the fourth one, Marcus suggests that when he is angered at people committing apparent wrongs, he should keep in mind that he too commits wrongs. I’ve modified this to a question a try to ask myself when annoyed at others’ actions: “how am I like this?” Asking this question takes my focus off others’ acts and focuses on myself, and how I am like those who I’m angry at in some ways. This helps me direct my energies to change myself rather than wasting time obsessing over others.

Meredith: I love Hipparchia’s quote in response to a misogynistic philosopher who criticizes her for learning philosophy:

Do you suppose that I have been ill advised about myself, if instead of wasting further time upon the loom I spent it in education?

Diogenes Laertius, Lives of the Eminent Philosophers, book 6

We wrote about this story in chapter 5 of our book, showing Hipparchia’s utterly bold, fearless attitude and her fight (quite literally, with Theodorus) to take a seat at the men’s philosophical table in ancient Athens. Outside of our book, a quote I often think about is:

That which has died falls not out of the universe. If it stays here, it also changes here, and is dissolved into its proper parts, which are elements of the universe and of thyself. And these too change, and they murmur not.

Marcus Aurelius, Meditations VIII, 18

I ponder this when I consider family and friends who have passed away and my own close calls. It helps me recall that we are both in and of nature, and that we are small pieces of the cosmos itself, which is ever-changing. It is beautiful.

Where can we find out more about you?

Massimo: Other than my books, most of my writings appear in my Substack newsletter, entitled Figs in Winter (Massimo Pigliucci), after a famous story in section 3.24 of Epictetus’s Discourses (check it out!). I also organize in-person retreats twice a year (winter and summer) where we take an in-depth look at different aspects of Greco-Roman philosophy. They are held in various locations in Europe, including Rome, Athens, and Paris. Finally, for many years I have been running a mixed in-person and online meetup called “The Philosophy Lab.” At the moment of this writing it has close to 9,000 members from all over the world. .

Gregory: Most of my Stoic activity nowadays happens at NYC Stoics, which holds online reading groups that people from around the world join and in-person meetups in New York City. The NYC Stoics page is where Massimo and I enroll folks for our annual in-person Stoic Camp in upstate New York, which is usually held in August, with registration opening February or March. You can also learn more about me and contact me through my personal website: greglopez.me.

Meredith: I invite folks to check out my Substack blog, Meredith Alexander Kunz, where I am posting currently, and the legacy blog site, here. It’s not just for parents and caregivers - it’s a wide-ranging look at life philosophy and Stoicism, from the point of view of a woman attempting to live it in the real world (and it’s often aspirational!).

I also launched a new podcast in 2025, The Philosopher’s Compass, where I talk with people who are working on practical philosophy, especially Stoicism, and we have conversations about what they’ve learned from pursuing it and how it gives their lives meaning. Guests offer valuable words of wisdom that I’ve learned a lot from. It’s a down-to-earth approach, very much focused on real-world experiences and guests’ own research into philosophy. You can find my podcast chat with Massimo and Greg here. I’m also on Instagram and on Bluesky too, and LinkedIn.

What questions would you like to leave us to think about?

• Massimo: What if your chosen philosophy of life turns out to be deeply flawed? Are you willing to drop it and seek something else? How would you go about it?

  I think we all have a philosophy of life, either because we inherited it from our parents and culture (e.g., most religions), because we have chosen it deliberately, or because we act in certain ways that reflect unconscious choices that could, nevertheless, be understood as a philosophy of sorts. But the Skeptics teach us that any of our beliefs could be wrong, so it is important, at least from time to time, to pause and reflect critically on what we have been doing and why. Most of the time we may decide that we’re good and keep going along the same path. But occasionally we may feel the need for a course correction, in which case we ought to be able to summon the courage and wisdom that it takes to effect such correction.

• Gregory: Is it actually worth having and practicing a philosophy of life? Why or why not?

  If you have strong views on the matter, perhaps take a page from the skeptics and attempt to argue against your own view, taking note of how strongly you held the view before and after arguing against it!

• Meredith: Do you have a life philosophy, and if you do, can you spell it out and explain how you’re living by it?

  Lots of folks have vague ideas about how to live, but a practical framework like Stoicism is much more valuable in determining how to make ethical choices and act with character and virtue, rather than just storing amorphous ideas in the back of your head. Do you spend time thinking about why you do what you do, and how it affects others? That’s important, because philosophy has an important role to play in how we express and support our common humanity. And if you have a philosophy you admire and are trying to live by, is it ok if you don’t always live up to it? I’d argue that trying and sometimes failing is just part of being human, and that Seneca’s “crawling towards virtue” is a perfect example of that.