Who gets to call themselves a Stoic? Michael and Caleb tackle the issue of who is and isn’t a Stoic. Grounding their discussion in Michael’s recent article:

(03:00) The Stoic alignment chart: theory purists to rebels

(11:00) Benefits of gatekeeping: maintaining truth and standards

(21:00) Epictetus as motivating gatekeeper

(26:30) Risks: pedantry and missing the forest for trees

(40:00) When gatekeeping becomes antisocial

(46:30) Finding the balance

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

https://ancientlyre.com/

Some Stoic ideas cut against modern culture. Michael and Caleb examine seven truths that challenge how we think about politics, anger, success, and evil.

The Stoics make claims most people won’t like hearing. Politics can’t ruin your happiness. Anger is always wrong. Being a victim doesn’t make you virtuous. You can’t choose all your obligations. Nearly everyone lives in luxury today. Some lives are objectively better than others. And no one truly wants to do evil.

(00:00) Politics can’t make you unhappy.

(09:00) Anger is never appropriate.

(19:40) Neither victimhood nor victory are moral credentials.

(26:10) You don’t choose all your roles.

(34:20) Nearly everyone today lives in luxury.

(39:10) Some lives are better than others.

(43:10) No one intends to do evil.

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

Caleb explores Seneca’s warning about wealth from Letter 17 and why material success may be a trap. The episode questions whether financial independence really delivers freedom or just creates new forms of dependence.

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

https://ancientlyre.com/

Michael and Caleb examine skeptical modes from Sextus Empiricus. These arguments show why you can’t trust your sense impressions.

The Stoics and skeptics were rival schools. But they agreed on one thing: most people live under illusion. The skeptics said you can never overcome that. The Stoics said you can, but only if you’re extremely careful. Both agree you need to interrogate every impression.

(3:20) Skeptics vs Stoics on impressions

(9:00) Different animals see differently

(15:30) Humans disagree with each other

(20:20) Your senses contradict themselves

(26:40) Your disposition changes everything

(31:50) The ideal disposition for truth

(35:10) What you’re next to matters

(39:00) Rarity distorts value

(39:53) Different cultures, different truths

(43:10) Why philosophy starts with dissatisfaction

(45:10) How far should skepticism go

(49:40) Summary of nine skeptical modes

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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/

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

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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/

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

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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

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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/