How to Be a Stoic: Using Ancient Philosophy to Live a Modern Life by Massimo Pigliucci (+ Book Club Discussion)

A philosopher asks how ancient Stoicism can help us flourish today. Whenever we worry about what to eat, how to love, or simply how to be happy, we are worrying about how to lead a good life. No goal is more elusive. In How to Be a Stoic, philosopher Massimo Pigliucci offers Stoicism, the ancient philosophy that inspired the great emperor Marcus Aurelius, as the best way to attain it. Stoicism is a pragmatic philosophy that focuses our attention on what is possible and gives us perspective on what is unimportant. By understanding Stoicism, we can learn to answer crucial questions: Should we get married or divorced? How should we handle our money in a world nearly destroyed by a financial crisis? How can we survive great personal tragedy? Whoever we are, Stoicism has something for us—and How to Be a Stoic is the essential guide.

Why I Picked It Up—The Context

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I'm a big believer that your connection to a book has everything to do with your timing and your needs. I'm a mood reader to my core. I might not be in the particular headspace for something but circle back a few months later, which is why I hesitate to ever label books DNF (did-not-finish, in book commentary circles.)

2024 has been a hard year overall, and I've grappled with being extraordinarily burnt out after 4+ years of absolute peak productivity. I successfully launched and ran my own business, wrote (then gutted and rewrote) a novel at least four separate times, have written at least 100+ articles in the past year alone, read 100+ books this year too (refreshing, promise), clawed my way up to the elusive vertical and bylines I wanted, maintained my fitness (and even majorly improved it), actually kept a social balance, etc,. etc,. Tried to keep it all in order.

But I've always been awful to myself whenever I haven't been able to handle the volume because "I should be stronger than that." And God forbid life circumstances get in the way!

I've been better this year about not automatically viewing emotions as a weakness (after all, I write fiction), but am still constantly navigating the line between pursuing excellence and discipline versus not solely defining myself by what I achieve. For that reason, any scale-back or shortcoming feels like I'm failing. Am I giving myself grace or excuses?

I appreciated the framework taught to me by a therapist I interviewed this spring: that perfectionism isn't automatically bad, but I need to determine when it's helpful to me (i.e. getting me to my goals) versus when it's causing unnecessary suffering.

In June, I hit a wall of exhaustion and despair but got through it. Now, several losses in a row just absolutely crushed me, and it kills me that I'm not immediately recovered and firing on all cylinders in the way I could normally.

Hence: Stoicism. I know I have the tools to force myself to get over anything (and that I'm stubborn enough that I will immediately level up after in some permanent way) but I still could use some philosophical comfort and a challenge to forcibly transform my brain. How can I feel less and be lighter, how can I not crash even after this much effort, how to detach from people and outcomes and the need for control. What is rational tiredness versus what's just not good enough?

Some people recommend the book The Perfectionist's Guide to Losing Control by Katherine Morgan Schafler for that purpose but to be honest, I found it immediately condescending and the phrasing to be a little corny. Not for me. This is much more in line with what actually helps me iron myself out.

Introducing the Concept of Stoicism

I had a vastly different idea of what Stoicism was when I picked this up. I've often romanticized the idea — God, I'd love to show zero emotion — but that's not entirely what the philosophy is in practice, as exemplified by thinkers like Epictetus and Cato the Younger.

It's more so about finding the line between what you can control and what you can't, then letting go of what you can't. (I perhaps saw it more as another form of Puritanism: ascetics and rigidity proving one's moral purity.)

Remember how I said I hate self-help books? This is exactly what I mean; I infinitely prefer to understand a fully-fledged philosophy, its ancient roots, its connection to Buddhism, and how it's unfolded in history when I'm deciding whether to (and how to) apply it to my own life. This book was an excellent example of being what I need as I embrace a problem, filled with helpful tidbits that I can lean into without being fed some watered-down advice on self-care and loving myself.

The Writing Was Just Okay

Admittedly, the writing lost me some. It feels a bit forced in its conversational tone in that it's secretly dry but wants to be the "fun" teacher. It's relatively easy to work through, but the overall structure feels somewhat disorganized, and I think it might have benefited from more clarity at the beginning.

Some of the anecdotes felt either too long or meandering, or tangentially relevant, so I'm not entirely convinced by the skill of the examples. (My favorite nonfiction writers can integrate supporting evidence pretty effortlessly.)

Of course, a lot of the examples used are focused on the Greeks and Romans, but I've read plenty of books in which ancient history examples are more engaging than they are here. It used a lot of transitions I don't love like "as you may remember" or "to deviate here, let's talk about X."

The Organization of the Book Might Be Hit-or-Miss

I couldn't really tell what I thought about the book's structure. For example, one section talks entirely about the mortal fear of death and how it influences Stoicism, which: fair. But not really something I'm personally interested in, and felt like it was given a little too much focus.

That emphasis is just helpful in reminding us that the world owes us nothing—that if we believe in the laws of organization of the universe (whether that's a deity or individual agency), it will not rearrange itself to spare you suffering or pain.

One chapter focused on those with significant health challenges and how to embrace a shitty roll of the dice. Another talked about dealing with anger or loneliness.

If anything, the practical chapter near the end tied everything together in a much more organized way—and in my opinion, should have been the beginning of the book. In it:

1. Virtue is the highest good.

2. Follow nature—apply reason to social life.

3. Dichotomy of control—Our decisions and behaviors are under our control; outside of our control is everything else.

4. Speak little and speak well. (I'm good on this one, I think—at least verbally, in person. The first category.)

The Thief and the Lamp

Overall, the Stoics put a lot of emphasis on moral purity being the force that guides their decisions; the aim of man is to be virtuous, although we may disagree on what exactly that means in practice.

“Virtue is the chief good because it is the only thing that is valuable under all circumstances and that helps us make proper use of things like health, wealth, and education.”

One particular example I loved is that of a thief stealing a lamp. In the example, the teller of the story talks about realizing someone has stolen his lamp. First, he thinks that it is replaceable. Next, he can prevent this sort of conflict in the future by opting for a cheaper lamp and better storage. Third, he may have lost a lamp but the thief lost his integrity in the process, whereas the Stoic has made decisions that align with his desire for virtue. So: he can't really control the outcome, and thus, there's no reason to be upset.

“It is not in our power to change the robber's judgement that forgoing his integrity in exchange for a lamp or wallet is a good bargain, but it is in our power to make the reverse judgement ourselves. Rephrasings, you may have noticed, are important in Stoicism.”

I have been stolen from before (as my car was broken into in college), and forever remember the feeling of violation; still, I did remind myself someone else made a choice to violate my security. I can take preventative measures, but beyond that—some misfortunes are about others' choices, which you cannot control.

Having this exchange focus for events that feel like frank bad luck is also newly helpful to apply. If you have been the victim of some random misfortune, you can take some comfort in knowing they've traded something (in this case: integrity) for it (if they have the same belief system.) If they don't believe in the same lines of rightness that you do, then they may be acting in the way that makes the most sense for them and thus it's not for you to criticize someone acting in line with their values, as that's Stoicism's highest calling.

“The APA tells us to change standard phrases like 'This is terrible!' to something along the lines of 'I'd rather not have to deal with this, but I can manage it, and getting angry isn't going to help me at all.'”

The book talked about the ancient Greek concept of amathia, which is that "it is more helpful to think of people who do bad things as mistaken and therefore to be pitied and helped if possible, not condemned as evil." (Which personally aligns a lot with my personal philosophy; I believe in God but not in Hell.)

I've definitely made the mistake in my conversations of calling certain actions "the right thing to do" in regards to my own politics, when in reality, everyone's moral standard is different. When someone pointed that out to me, it was a necessary but uncomfortable reminder that my way is definitely not the only way and "right" is variable (which actually resonates a lot with the concept of this book.) And of course, that's not entirely amathia because it's not "bad" to have a different take than me. Perhaps I've been closed-minded in some concepts.

It's harder to use the same Stoic rationality when it comes to people or relationships upsetting you rather than an absent thief. But in that case, Stoicism actually draws from concepts recognized in a favorite book of mine, You're Not Listening: What You're Missing and Why It Matters by Kate Murphy.

“We don't find all of [suggestions] in the ancient Stoic texts, but they're all in synch with the fundamental Stoic idea that to live a good life, we have to learn about how the world actually works (as opposed to how we wish it would work), and that we must also learn to reason correctly in order to best handle the world as it is.”

I'm definitely guilty of having a rosier view of the world than it actually deserves, so I should balance optimism more with this awareness. I try to be as open as possible, but struggle with balancing openness and detachment.

There Are Still Aspects I Disagreed With

One interesting aspect of Stoicism includes disconnecting from a material world and temporary people—which is a noble pursuit, sure.

To a certain extent, I do agree with the book's claims that what you say becomes who you are and that virtue is a guiding force. But also, who and what you surround yourself also becomes who you are? I enjoy beauty (and technically review possessions for work—I know, I know) but I'm grounded in knowing they do not contribute to my substantial happiness or meaning. But I think it's a slippery slope between detachment and losing significance/joy/faith. Surely, you at least hope some things will last?

When Tampa was braced to get wrecked by Hurricane Milton and we feared losing our home, I got some genuine comfort from realizing that beyond my requests to save journals and family jewelry if possible, I was not as devastated by the thought of losing items, just afraid of losing people I love. It was the "what would you save from a burning house?" question in practice, and in reality: very, very little mattered in my ten-minute FaceTime instructions.

Part of why I study aesthetics is because I do think that appreciating your material reality does substantially contribute to your self-identity and your sense of permanence. Even if that's as small as a living area you've created as a reflection of yourself or an item connected to a hobby that is permanent when friends, lovers, etc,. may pass through in this temporary, uncontrolled way as Stoicism says. Especially when a big focus of Stoicism is gratitude for small moments, which you can appreciate more in contrast to the negatives you're faced with. That being said, I've definitely talked with other commerce/shopping writers about the ethics of consumption as a whole. (On my reading list: Possessed: Why We Want More Than We Need by Bruce Hood.)

The book also says to cast away friends who talk about shallow things or who don't only want to discuss "serious matters" at the dinner table, but levity is a much-needed resource for getting through (and fundamentally enjoying) life. Sure, your ideal population of guests and friends may prefer to ruminate on deeper things, but it sounds pretty isolating and obnoxious to disregard the textures, conflicts, and interests of daily life no matter how "small" they seem. Perhaps a little self-important.

Even the book says humor is an effective way to cope with anger, loss, and loneliness, so it feels strange to not also appreciate lightness as a necessary ingredient. Plus, examples like the writer going into a bank to close out an account and explain to the bank teller — who is likely not paid enough to care — why they have an ethical dilemma with the larger corporation's practices felt overly obnoxious.

I love that it talks about gossip being anti-Stoicism because I've always been very anti. It just goes against my personal values. I like its emphasis on gratitude and being in the moment rather than dwelling on the fear of loss, but of course, I do think part of what makes something beautiful and meaningful to you is the belief that it will last rather than judging everything only by how it most affects you in the current moment. It feels like the latter doesn't give people or things the room to not be pleasing at all times.

Even the book admits that the Stoics were "overly optimistic about how much control human beings have over their own thoughts." We have encountered more studies since the advent of this philosophy that unconscious influences affect our behavior, that we become an average of the people we're most often around, that our physical environments impact our mood and focus, etc,. etc,. that somewhat degrade the black-and-white claims of Stoicism. People and things impact us more than we think, and I think it's okay and also admirable in many ways to be moved by them, but of course, it's still a helpful model.

Overall, It's a Good Read.

The framework of Stoicism is overall helpful to me. It emphasizes that character and virtue is most worth pursuing, and you're living a good life so long as you're acting in accordance with those principles. Many actions are neutral actions, being that they're fine so long as they don't deviate you from your practice of those aligned deeds.

“To a Stoic...a decent human life is the cultivation of one's character and concern for other people (and even for Nature itself) and is best enjoyed by way of a proper—but not fanatical—detachment from mere worldly goods.”

“The discipline of desire (also referred to as Stoic acceptance) tells us what is and is not proper to want. This, in turn, derives from the fact that some things are in our power and some are not.”

According to Stoicism, one can regulate desire with courage (to face facts and act accordingly) and temperance (to rein in our desires with what is achievable.) I know I'm brave, but could be better about being temperate. Then, you want to focus your energies on where you have the most control. Your confidence lies in knowing you did whatever was in your power to do.

In general, this is why I push myself so hard. Because at the end of the day, I know I did whatever I could and put in as much effort as possible, and that helps quell the regret. That doesn't save me from wishing I'd acted differently or that things had turned out differently, but it still gives me the confidence of knowing that I've tried. Still, Stoics claim that regret is a waste of energy, but for me, the confidence of knowing that I tried my hardest does dovetail with regret: because it still may not have worked. My regret might stem from hindsight bias and being aware that my calculation still might not have been good enough. Logical? Maybe not. But it's there.

“We live in far too intricate social environments to always be able to do the right thing, or even to do the right thing often enough to know with sufficient confidence what the right thing is to begin with.”

On that note, Stoicism encourages you not to base success on outcome (a work in progress pour moi.) The philosophy also talks about how just because something is natural doesn't mean it's good. How to develop an internal alarm system of knowing when to shift from suffering to action. Also: fake it 'til you make it, often. You can still decide the most rational course of behavior and force yourself to do it until it's just muscle memory.

“The other side of endurance is resilience, and resilience is empowering.”

I do think embracing Stoicism and expecting total emotional equilibrium may be easier said than done, and that it can be cold if done without regards for others. It does sort of assume that you should always know what is "right" to you and thus have complete control over yourself. Avoiding regret, etc,. assumes that you are not revising your moral code and realizing that—although you did your best at the time—things could have turned out differently had you known.

The writing wasn't my favorite, but the philosophies were interesting and the book was overall pretty easy to read even when it meandered. I'd love to apply some of these insights, and really resonated with a lot of the intention behind the philosophy.