Ever say yes when you meant no?

Caleb and Michael explore Plutarch’s guide to resisting pressure and not being a pushover.

Plutarch identifies the root problem as oversensitivity to shame. You care too much about violating social norms.

The conversation covers when to respect social convention versus when to break it. They examine historical examples of caving gone wrong, from Creon and Medea to murdered dinner guests. The key insight is that caving makes things worse while standing firm with tact makes things better.

(04:47) The Pushover: Oversensitivity to shame versus shamelessness

(12:20) Mythical and historical examples of caving to pressure

(22:20) Starting small: Rejecting social drinking and suffering fools

(26:10) Giving honest feedback despite discomfort

(32:10) Ten reflections on resisting pressure

(41:30) Personal examples of caving and standing firm

(43:40) Rules for not giving in

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Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

When you’re in prison waiting to die, what can philosophy do for you?

Michael and Caleb read Boethius’s Consolation of Philosophy - a book written by a Roman senator facing execution.

It’s philosophy tested at the breaking point. The book works through arguments for why you shouldn’t be angry at fortune. Some are practical - don’t complain about losing externals when externals always change. Others cut deeper - fortune can’t touch what matters most, which is yourself.

The interesting part is watching someone work through these arguments for real, not as theory.

(03:20) Historical context and influences

(09:00) Book structure and Lady Philosophy

(13:50) Fortune hasn’t changed, it was always fickle

(16:40) You chose to value externals, don’t complain when they shift

(18:40) Fortune gave you everything, can’t be mad it took it back

(21:30) Don’t overweight current misfortune

(29:30) Fortune can’t affect what matters - yourself

(34:40) External riches aren’t valuable anyway

(38:00) External honors aren’t valuable anyway

(42:10) Preview of Book Three - defining the good

(45:30) Final thoughts on the book

Download the Stoa app (it’s a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

Nothing stays the way you want it. Your job disappears. Relationships end. Everyone you know will die. The cities you live in will cease to exist. Michael and Caleb explore three Stoic strategies for accepting what you can’t control.

(03:20) The Word “Nostalgia”

(04:10) Strategy 1: Nothing Belongs to You

(12:20) Strategy 2: Expand Your Time Horizon(19:20) Thinking in Life Stages

(25:20) Strategy 3: Finding Agency in Change

(29:30) Combining the Whole and the Part

(35:30) Athletes Who Can’t Let Go

(39:50) Just Do What Nature Demands Now

(43:30) Summary and Synthesis

Download the Stoa app (it’s a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations: https://ancientlyre.com/

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This episode is taken from our recent Substack Live episode where we covered reader questions. Follow us on Substack: https://www.stoaletter.com/ to catch the next one.

How much ancient philosophy should you steal? Caleb and Anya Leonard from Classical Wisdom explore the art of philosophical eclecticism, from Heraclitus’s cryptic fragments to philosophical rivals between Stoics and other schools.

We start with Heraclitus, the riddling philosopher who wrote that you can’t step in the same river twice. His idea that strife creates harmony deeply influenced the Stoics. But he was deliberately obscure - even Socrates admitted he needed a “deep diver” to understand him. From there we discuss Skepticism and Epicureanism.

(00:03:57) Flux and constant change

(00:12:24) Providence vs chaos

(00:15:21) Is strife justice

(00:21:30) Fragments worth contemplating

(00:22:41) Skepticism: How we know what we know

(00:29:00) The Stoic-Skeptic debate

(00:31:00) Suspending judgment in heated times

(00:35:28) Epicureans and calculated pleasure

(00:39:00) Simple pleasures vs hedonism

(00:44:22) The value of eclecticism

Download the Stoa app (it’s a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

Philosophy talks about big ideas. The good life. Virtue. Happiness. But talking about aspirations isn’t enough. You need mechanisms—concrete practices that actually change behavior.

Caleb examines why serious thinkers focus on mechanisms over aspirations. Discussions about mechanisms force action and generate information. Discussions about aspirations turn into complaints about the world.

The Stoics were good at this. They didn’t just discuss anger. Seneca and Marcus Aurelius gave specific advice about becoming less angry. They broke virtue down into smaller parts: self-control becomes orderliness, propriety, modesty, self-mastery. Each breakdown gets more specific and decision-relevant.

But you can’t ignore aspiration entirely. You need both the effective cause (what brings about change) and the final cause (where you’re going). Training and performance. The concrete and the universal. The Stoic sage sees and acts with both the whole and the part in mind.

Philosophy is tricky because the problems are abstract. But that’s exactly why you need to speak at the right level of detail. Mechanisms for a purpose. Aspirations to set the target. Concrete practice to get there.

Download the Stoa app (it’s a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

Sam Alaimo is a Navy SEAL who discovered Stoicism after leaving the military. He is a cofounder of Zero Eyes, an AI company stopping gun violence, and writes at whatthen.org.

Caleb and Sam discuss how affluent societies need philosophy, whether virtue alone makes life good, and why Ernst Jünger remains one of history’s most fascinating thinkers. The conversation moves from ancient philosophy to World War I trenches to the risks of letting AI do our thinking.

(00:00) Sam’s background and writing journey

(04:00) How Stoicism helped after military service

(06:20) Why affluent societies invented Stoicism

(08:00) AI as a war on human reason

(10:30) Epictetus: the most extreme example

(15:00) Marcus Aurelius: emperor and philosopher

(20:10) Why Epictetus avoided the word “virtue”

(24:10) Stoicism as energetic, not passive

(26:20) Where the Stoics got it wrong

(30:20) Existentialism and Stoicism on freedom

(34:20) Ernst Jünger: war hero and philosopher

(38:20) Storm of Steel and phenomenology of war

(44:30) Philosophy divorced from reality

(47:20) Jünger’s fiction and diaries

Download the Stoa app (it’s a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

Have we traded ancient wisdom for modern myths?In this episode, Caleb speaks with Cornell classics professor Michael Fontaine.

Fontaine argues that psychiatry and mythology both offer competing stories about human suffering. The ancients had three models: medical treatment, spiritual purification, or taking responsibility for your choices. Today we’ve mostly picked door number one and forgotten the rest.

How to Have Willpower

(9:20) A Forgotten Distinction: Reasons vs Causes

(19:30) Freedom and Responsibility

(31:20) Death, Souls, and Scientific Myths

(49:30) Ancient Philosophy for Secular Students

Download the Stoa app (it’s a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

Caleb explores why anger works as social currency. If you're not angry when someone hurts your friend, do you really care about them?

People aren't wrong to read meaning into your emotional responses. If most angry people care and most calm people don't, anger becomes useful data. The Stoic who stays calm has to work harder to prove they care.

(00:00:00) Introduction and context from Donald Robertson episode(00:02:10) Anger as social emotion vs internal emotions(00:03:10) Political case study: anger as tribal signal

(00:04:50) How anger serves as political signaling(00:05:10) Social incentives to express anger(00:06:00) The difference between expressing and feeling anger

(00:07:00) When loved ones expect your rage(00:07:20) The logic of anger as caring(00:08:00) Why people use emotional heuristics

(00:09:40) How Stoics must prove they care(00:10:00) The burden of showing character through actions(00:10:40) Why managing emotions is just the beginning

Download the Stoa app (it's a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we'll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

Caleb and Michael interview Donald J. Robertson on Anger and Stoicism.

We’ll be doing more live events and chats. Get the Substack app and stay tuned.