When I spoke with Massimo Pigliucci, I was halfway through listening to How to Be a (Happy) Skeptic. I liked the combination: a book about living well that also asks you to question the advice you're being given.
That includes the advice in philosophy books.
If you're looking for a first Massimo Pigliucci book, start with How to Be a Stoic for an introduction to practical Stoicism, A Handbook for New Stoics for weekly exercises, or How to Be a (Happy) Skeptic for thinking clearly when you can't be certain. The right starting point depends on what you want to work on.
Below is a guide to eight books he has written, co-written or edited, with reading routes and the full interview.
Listen above, watch the conversation on YouTube, or keep reading to choose a book.
What our conversation changed about the reading question
I asked Massimo whether scepticism helps someone who already questions everything and struggles to act. His answer separated confidence in yourself from confidence in your evidence. The question is how well a particular belief is supported.
That distinction makes this a useful companion to Stoicism. You can follow a philosophy while continuing to examine its claims. In the interview, Massimo describes himself as primarily a Stoic with a sceptical attitude.
He also recalls visiting a bookshop in Rome with his grandfather every weekend as a child. His grandfather made suggestions, but Massimo chose the book. Later in our conversation, he stresses taking notes and discussing what you read.
So I'd choose one book around a question you care about. Give the author a fair hearing. Then try an idea in your own life and see where it holds up.
Which Massimo Pigliucci book should you read first?
| What you want | Start here | Why this fits |
|---|---|---|
| An introduction to living as a modern Stoic | How to Be a Stoic | The broad starting point for Stoic philosophy and everyday choices |
| A practice you can return to each week | A Handbook for New Stoics | 52 lessons with exercises, co-written with Gregory Lopez |
| Better judgement under uncertainty | How to Be a (Happy) Skeptic | Cicero, inquiry and the practical uses of doubt |
| Short readings you can revisit | A Field Guide to a Happy Life | 53 brief lessons adapting Epictetus for modern life |
| Ancient philosophy beyond one school | Beyond Stoicism | Thirteen Greek and Roman thinkers, with exercises |
| A closer look at science and pseudoscience | Nonsense on Stilts | How to judge scientific claims and expertise |
These are reading suggestions, not a requirement to buy a stack of books. The publisher links below give editions and formats so you can find the version you want, including through a library.
How to Be a Stoic
Start here if you're new to Pigliucci's practical philosophy. First published in 2017, this book connects Stoicism with questions about how to live and respond to difficulties. It gives you a broad frame before you commit to a more structured workbook.
Keep one everyday situation in mind as you read. Which part of it calls for a change in your judgement or conduct? That makes the philosophy easier to test than collecting quotations.
Book details and editions at Basic Books.
A Handbook for New Stoics
Pigliucci and Gregory Lopez organise this 2019 book around 52 weekly lessons. Choose it when you've read enough to understand the appeal of Stoicism and want some structure for practising it.
The weekly format gives you time to repeat an exercise. You don't have to finish every lesson before doing something useful.
The publisher also provides printable exercise pages, which is particularly helpful if you use the ebook.
Book details and exercise resources at The Experiment.
How to Be a (Happy) Skeptic
Published in June 2026, this is the book at the centre of our interview. Its full subtitle is The Power of Doubt in a Meaningful Life: Lessons from Cicero's Philosophy. Pigliucci uses Cicero's life and writings to explore judgement and living well, including friendship, citizenship and grief.
Cicero belonged to the sceptical Academy and drew on Stoic ethics. Calling him simply a Stoic loses an important part of the story; the Stanford Encyclopedia's account of Cicero explains the distinction.
Choose this book if you want convictions you can act on while remaining willing to reconsider them. As you read, ask what would count as a good reason to change your mind.
Book details at Penguin Random House.
A Field Guide to a Happy Life
This short 2020 book presents 53 lessons through a modern adaptation of Epictetus's Handbook. It suits readers who want brief passages to return to during the week.
It is Pigliucci's adaptation, rather than a translation you should quote as Epictetus's exact words. If a passage interests you, comparing it with a translation of the ancient text can become part of the reading.
Beyond Stoicism
Published in 2025 and co-written with Gregory Lopez and Meredith Alexander Kunz, this book introduces thirteen Greek and Roman thinkers and includes exercises for trying their approaches.
Choose it if you're curious about what Stoicism leaves out, or want to compare it with other ancient philosophies. Use the differences to ask where each approach helps and where you disagree.
If you have the first printing, the publisher notes a duplicated page and supplies the correct page 118. That replacement is available on the book's page.
Book details and the page correction at The Experiment.
The Quest for Character
This 2022 book uses the story of Socrates and Alcibiades to examine character and leadership. It asks what philosophy can teach someone who wants power, and what we should expect of those who hold it.
Read it when your question concerns becoming a better person, or recognising whether a persuasive leader also has good judgement. Knowing the right words and acting well can come apart.
How to Live a Good Life
Edited with Skye Cleary and Daniel Kaufman, this 2020 collection brings together fifteen contributors writing about philosophical and religious approaches to life.
It's the wider comparison to choose if your question is whether Stoicism is the philosophy you want to practise. The chapters give different traditions room to speak in their own voices.
Try reading a chapter from a tradition you know little about. Write down its strongest argument before deciding whether you agree.
Book details at Penguin Random House.
Nonsense on Stilts
This book turns towards science and pseudoscience: how scientific knowledge is made, interpreted and sometimes misrepresented. The revised second edition was published in 2018.
Choose it if claims about evidence interest you more than daily Stoic exercises. It is a useful next direction after the interview's question about how you know something. It also asks how to recognise expertise without pretending you can personally investigate every field.
Second-edition details at the University of Chicago Press.
A reading order that serves your question
For a practical Stoic route, I'd begin with How to Be a Stoic, then work slowly through A Handbook for New Stoics. Keep A Field Guide to a Happy Life for shorter readings.
If the interview brought you here, start with How to Be a (Happy) Skeptic. Follow it with Beyond Stoicism if you want to compare ancient approaches, or Nonsense on Stilts if you want to examine claims about science.
For the widest comparison, start with How to Live a Good Life. You can choose a tradition to investigate further after hearing several cases.
Pick the question before the book. You can change the route once you've started.
Try this with your next chapter
Massimo describes occasionally arguing for a position he disagrees with. Here's a small reading exercise based on that discussion.
Choose one claim in your next chapter that you initially reject. Write a paragraph making the strongest case for it, using the author's reasons. Then write your objection and name the evidence or argument that would make you reconsider.
You may still disagree. But you now have something more specific to examine than whether the author sounds convincing.
Being open to revision also doesn't make every position equally well supported. In our conversation, Massimo recommends matching the confidence you need to what's at stake. A low-cost, reversible choice can tolerate more uncertainty than a consequential one.
Keep listening and reading
Listen to the full interview on Buzzsprout or watch it on YouTube. We discuss changing your mind, giving advice, reading with children and the difference between self-doubt and examining evidence.
Massimo publishes essays at Figs in Winter. His official book catalogue includes his wider work in philosophy and science.
For a way to record what you're trying, use the Stoic journal template based on Pigliucci's method. For a broader list of ancient and modern authors, see Donald Robertson's Stoicism reading list.
If you want structured practice, the 7-Day Stoic Challenge is free. Nine audio lessons and a 42-page workbook.