Stoa Conversations: Stoicism Applied

In this episode, Caleb and Michael explore how Stoicism reframes our understanding of risk, teaching us to embrace uncertainty while focusing on what truly matters. They discuss:

• Why Stoics aren't reckless, but cultivate caution
• How Stoicism offers the highest reward with the lowest real risk
• Critiques that Stoicism is for the risk-averse, and why they fall short
• Why Stoicism may provide the ultimate psychological aid for meaningful risk-taking

Learn how ancient wisdom can help you navigate life's gambles with grace and purpose. The Stoics knew: true risk lies not in external outcomes, but in compromising your character.

***

Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

Download the Stoa app (it’s a free download): 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/

Is Stoicism just toxic positivity? No, obviously.

But what's the difference between toxic positivity and unrealistic optimism?  And how can Stoics avoid the real risks of both?

In this episode, Caleb and Michael dive deep into Stoic practice and its alleged similarity to toxic positivity. 

***

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

Download the Stoa app (it's a free download): 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.

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

The Stoic art of solitude and self-consistency

Can you be alone with your thoughts? Seneca's Letter X challenges us to master the art of solitude.

In this conversation, Caleb and Michael unpack Seneca's advice on solitude and explore its relevance in our hyperconnected world.

(00:58) The Paradox of Solitude

(05:40) Consistency Between Private and Public Life

(12:35) The Dangers of Isolation

(19:08) Keeping Others and Nature in Mind

(26:12) Is Solitude a Goal?

(31:04) The Internet: A Modern Challenge to Stoic Principles

(35:00) Becoming a Friend to Oneself

***

Listen as they discuss the Stoic approach to balancing social engagement with self-reflection, the importance of character in both solitude and company, and how to cultivate a healthy relationship with oneself.

Download the Stoa app (it's a free download): 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/

Join Caleb and Michael as they dissect the mental game of competition and explore how ancient philosophy can give us an edge in modern battles – both on and off the mat.

In this gripping episode, Caleb shares his experience competing in his first Brazilian Jiu-Jitsu tournament and the valuable lessons he learned about applying Stoic principles under pressure. Michael, who has competed hundreds of time, offers advice and challenges Caleb along the way.

Whether you're a martial artist, a competitor in any field, or someone looking to apply Stoicism to life's challenges, this episode offers actionable insight on maintaining composure and clarity – as well as challenges and reflections on how to apply Stoicism to jiu jitsu in particular.

(02:48) Jiu Jitsu Competitions

(04:58) What Is Jiu Jitsu

(07:05) Why Compete

(12:54) How Did It Go?

(17:23) Michael on Caring And Stoicism

(21:26) Michael's Advice For Caleb

(29:08) Should You Use The Restroom?

(35:06) Zooming In Too Much

(36:41) Epictetus vs Marcus on Competition 

(39:24) Participation Trophies Matter

(43:11) Caleb Doesn't Like Participation Trophies

(46:15) Social Resistance And Ego

(54:05) Caleb's Learnings

***

Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

Download the Stoa app (it’s a free download): 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/

Diogenes: the man who lived in a barrel and inspired Stoic philosophy.

In this episode, Michael and Caleb explore the life and ideas of Diogenes the Cynic - one of the most influential and eccentric philosophers of ancient Greece. They discuss:

(00:00) Epictetus on Diogenes' Freedom
(03:21) Diogenes' Life and Connection to Stoicism
(08:29) Diogenes' Approach to Philosophy
(15:59) Looking for an Honest Man
(21:27) Behold a Man – Plucked Chicken
(26:12) The Cup
(30:00) You Need A Master
(34:35) Alexander the Great – So Called
(39:00) Takeaways: Epictetus on Diogenes
(44:48) Favorite Diogenes Stories

Download the Stoa app (it's a free download): 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 Ontiveros speaks with Johnathan Bi, an entrepreneur and philosopher, about Friedrich Nietzsche's critique of Stoicism and egalitarianism.

The conversation begins with Jonathan sharing his personal journey from STEM to philosophy, setting the stage for a deep dive into Nietzsche's challenging ideas. They explore Nietzsche's opposition to Stoic egalitarianism and his concept of "higher men." The discussion delves into the psychology behind moral beliefs and value systems, examining how Nietzsche's insights can be applied to critically examine our own philosophical commitments.

https://greatbooks.io/

Johnathan’s YouTube

(01:50) From Hating Humanities to Loving Philosophy

(06:06) Silicon Valley Detour

(11:01) The Life of Action VS Contemplation

(19:58) Philosophy as a Way Of Life

(27:43) Nietzsche's Challenge To Stoicism

(31:04) The Equality Illusion

(39:20) Nietzsche on Epictetus

(50:04) Nietzsche For Every Day Life

(56:31) Why Ad Hominems Win & Metaethics

***

Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

Download the Stoa app (it’s a free download): 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/

In this episode of Stoic Conversations, Michael Tremblay offers a deep dive into one of Stoicism's most popular concepts: the Dichotomy of Control. Drawing from his 2021 article for the Modern Stoicism blog, Tremblay explores common misunderstandings about this principle and provides a more nuanced interpretation aligned with authentic Stoic philosophy.

Key points covered:

1. Misinterpretations arising from the English word "control"
2. Two common misunderstandings:Control as absolute ability to decide
   Control as strong influence
   
3. A more accurate interpretation: what depends on us vs. what doesn't
4. Practical applications of this refined understanding

https://modernstoicism.com/what-many-people-misunderstand-about-the-stoic-dichotomy-of-control-by-michael-tremblay/

***

Download the Stoa app (it’s a free download): 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/

Should Stoics become rich? What is your relationship to money?

Caleb speaks with Darius Foroux about his new book The Stoic Path To Wealth. They discuss a practical investment strategy and how Stoics should think about investing.

https://dariusforoux.com/

https://stoicpathtowealth.com/

(00:50) Darius's Story

(04:32) Stoicism

(11:51) Your Relationship With Money

(22:37) Becoming Rich

(34:25) Avoiding The Sidelines

(42:07) The Miracle of Compounding

(50:02) Role Models

***

Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

Download the Stoa app (it’s a free download): 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/

The ancient Stoic, Arius Didymus, provided a framework for practical wisdom and prudence. It’s still applicable today.

Courage

Moderation

(02:29) Reading

(05:01) Judgment

(17:19) View

(26:24) Shrewdness

(31:11) Discretion

(37:38) Soundness of aim

(41:31) Resourcefulness

***

Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

Download the Stoa app (it’s a free download): 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/

Michael and Caleb discuss the differences between modern self help and Stoicism – where self help is useful, where it isn’t, and recommend their favorite self help books.

(04:07) Defining Self Help

(11:31) Where Self Help Goes Wrong

(28:09) The Good in Self Help

(45:02) Best Self Help Books

***

Download the Stoa app (it’s a free download): 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/