Perennial Wisdom

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You’ve likely experienced the optimistic reset: a fresh note, a new week, and a well-crafted routine. It includes things like reading, prayer, or exercise. Then life happens. A late night. A tough conversation. A sick day. A looming deadline. One miss becomes two, and suddenly the whole “system” feels like a verdict: “I’m inconsistent.”

A “Rule of Life” is designed to protect you from this cycle of success and failure.

Think of it less as “rules” and...

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Today’s essay is about something most of us rarely talk about.

Quitting.

From the time we’re young, we’re taught to admire perseverance.

And often, that advice is wise.

But not always.

Sometimes the bravest, clearest, most honest act is not to continue—but to quit. Not from laziness. Not from fear. But from truth. From discer...

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Many of us treat our inner life like a home renovation project.

If I could just fix my overthinking, my consistency issues, my need for approval, and my procrastination, I could finally become “the person I’m supposed to be.” Yet often, the more we try to fix ourselves, the more tense and self-doubting we become—it’s like we are managing a difficult employee in our heads.

Here’s the uncomfortable truth: much of self-im...

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Christmas invites us to reflect on gifts, but the most meaningful one is the hardest to give. It isn’t bought or wrapped; it has nothing to do with ribbons or receipts. The true “present” of Christmas is presence itself—the quiet courage to be here, fully, without rushing past your own life. 

Before we offer anything to others, Christmas calls us to accept this moment as a gift. But that’s not usually how the season feels. ...

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Before we begin, it may help to name the kind of territory we’re entering—because this essay (or episode) is all about paradoxes and polarities.

A paradox is two things that seem to oppose each other but are both true. Similarly, a polarity is a pair of truths that don’t cancel each other out—they balance each other.

You experience this every day. You can want independence and connection at the same time. You can fee...

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In this episode of Perennial Wisdom, we explore the profound and surprising vision of happiness taught by the 13th-century theologian and philosopher St. Thomas Aquinas. Long before modern self-help, Aquinas argued that most of our suffering comes not from pain itself, but from aiming our deepest desires at things too small to satisfy them.

Through three core ideas, we examine why:

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In this episode of Perennial Wisdom, we explore the art of boredom: a journey through ancient philosophy, psychology, and modern thinkers like David Foster Wallace. From the desert monks who believed stillness revealed the soul, to Pascal’s warning that our fear of silence shapes our entire lives, to modern research showing boredom can unlock creativity. 

We talk about why boredom is so uncomfortable, how it shows us what we really want, and why we often use di...

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In this episode of Perennial Wisdom, we trace a journey from the streets of ancient Athens to the inner life of a restless bishop. Socrates challenges us with the idea of the unexamined life, while Augustine encourages us to look inward and seek truth within the depths of our own souls. Along the way, we examine how ancient rhetoric, self-persuasion, and spiritual reflection can help us break free from groupthink and reclaim our inner freedom.

This epi...

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In this episode of Perennial Wisdom, we enter the world of Arthur Schopenhauer—the philosopher of pessimism, and, unexpectedly, a teacher of compassion. Schopenhauer believed that happiness cannot be found by escaping suffering but by understanding it. Life, he wrote, “swings like a pendulum backward and forward between pain and boredom,” yet within that rhythm lies a quiet freedom—the freedom of acceptance.

Drawing from The World as Will and Representation and On the Basis of Morality, this reflec...

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In this episode of Perennial Wisdom, we sit down with Søren Kierkegaard, the 19th-century Danish philosopher often considered the father of existentialism. Specifically, we explore insights from his book Either/Or, which addresses one of life’s toughest questions: How do we live when every choice feels like a loss?

Kierkegaard believed that to live at all is to make a choice. And every choice—whether we act or remain still—shapes who we become.

<...

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In this episode of Perennial Wisdom, we explore the moral and psychological depth of Fyodor Dostoevsky, one of the greatest novelists and spiritual thinkers in history. From his near-execution in 1849 to his rebirth in the prisons of Siberia, Dostoevsky’s life became a living parable of human suffering, redemption, and love.

Drawing from Crime and Punishment, The Brothers Karamazov, and The Idiot, we uncover three perennial lessons for the modern world:

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In this episode of Perennial Wisdom, we explore the life and thought of Immanuel Kant through the lens of three enduring philosophical questions: “What can I know?” “What should I do?” “What may I hope?” Drawing on Kant’s groundbreaking ideas from The Critique of Pure Reason and The Critique of Practical Reason, we walk through his views on knowledge, morality, and hope.

Kant’s philosophy offers us tools for navigating uncertainty, making ethical decisions, and sustaining hope in...

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In this episode of Perennial Wisdom, we turn to the provocative thoughts of Friedrich Nietzsche (1844—1900) to explore one of the most overlooked yet essential inner struggles: the fear of change.

Building on the previous episodes—Socrates on the Fear of Death and Maslow on the Fear of Greatness—we now face Nietzsche’s challenge: to become who we are. Through poetic reflection and profound insights from Nietzsche, we explore how change is both essential and frightening.

<...

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In this episode of Perennial Wisdom, we explore a hidden but deeply human struggle: the fear not of failure—but of greatness. Drawing from Abraham Maslow's insights, we consider what it means to avoid our potential and why many of us unconsciously choose comfort over potential. 

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In this episode of Perennial Wisdom, we turn to Plato’s Apology and the final words of Socrates to explore how philosophy can liberate us from the fear of death. Socrates stood trial, was sentenced to die, and yet he remained calm, unshaken, and grounded in virtue. For Socrates, living an unexamined life poses a greater danger than death.

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In this episode of Perennial Wisdom, we turn to the life and teachings of St. Francis of Assisi to uncover a countercultural and liberating truth: true joy is not found in comfort, success, or status—but in humility, simplicity, and love.

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In this episode of Perennial Wisdom, we discuss why we often struggle to see ourselves or life clearly, and how to calm restless minds while examining our perceptions and our place in the cosmos. We focus on what it means to “look again” at life—to pause, to notice, and to practice humility and wonder. 

This episode draws on insights from spiritual teacher Ram Dass, philosopher Socrates, psychologist Adam Grant, and astronomer Carl Sagan.

Key Tak...

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In this episode of Perennial Wisdom, we examine an essay from the “Know Thyself” series on The Philosophy of Desire. You can expect to learn about the influence of desire in our daily lives. Why desire often shapes our decisions, self-image, and emotional states. This is volume one of a 10-part series on the art and science of self-awareness. If you’d like access to this series, consider becoming a Perennial Meditations member.

Key Takeaways

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Today, on this Sunday edition of Perennial Wisdom, we are turning to the pre-Socratic philosopher Heraclitus, who famously said,

Heraclitus believed that everything and everyone is in a constant state of change. While this idea might seem unsettling, he presents it not as a threat but as a vital key. To live well, we mu...

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In this episode of Perennial Wisdom, we discuss the timeless truths shared across cultures and traditions that guide us in cultivating a life well-lived. Rather than chasing life hacks, quick fixes, or fleeting trends, expect to learn why perennial wisdom invites us to slow down and return to what truly matters: cultivating character and finding meaning beyond ourselves.

Key Takeaways

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Today, on this Sunday edition of Perennial Wisdom, we reflect on humility—not as weakness or self-negation, but as wisdom—through the voice of one of the great spiritual teachers: St. Benedict of Nursia.

St. Benedict lived in the sixth century, during a period of political chaos and moral confusion. From this turmoil, he initiated a quiet revolution—a rule of life centered on prayer, work, and stability. His Rule became the basis for Western monasticism and conti...

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Today, on this Sunday edition of Perennial Wisdom, we turn to one of the great pillars of Western philosophy—Plato—and his vision of the Good. Not just goodness in the moral sense but the ultimate source of truth, beauty, and being.

Plato held that each human soul is inherently attracted to something ultimate. Though we might not always be conscious of it, beneath our pursuits for success, pleasure, approval, or knowledge lies a deeper desire—a longing...

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In this episode of Perennial Wisdom, we delve into how philosophy offers healing, not by curing mental illness, but by guiding us to live with clarity, freedom, and meaning. By drawing insights from ancient philosophy, theology, and Therapy for the Saneby Lou Marinoff, this episode explores philosophy’s role as a medicine for the soul. 

Key Takeaways

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In this episode of Perennial Wisdom, we turn to monks and the monastic life for wisdom. In this video essay, we explore how to “Think like a Monk” by drawing from The Wandering Mind by historian (and previous podcast guest) Jamie Kreiner, as well as the wisdom of early Church Fathers. Expect to learn how medieval monks battled distraction, cultivated silence, practiced simplicity, lived lives of service, and much more. 

Key Takeaways

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In this episode of Perennial Wisdom, my guest is Shane Trotter (author of Setting the Bar). In our conversation, Shane and I explore the complexities of character development, focusing on themes such as responsibility, discipline, and societal context. We also discuss the challenges of balancing personal and professional responsibilities, the importance of clarity in priorities, the distinction between duty and obligation, and much more. 

Key Takeaways

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In this episode of Perennial Wisdom, my guest is Prof. Dean Rickles, the author of Life is Short: An Appropriately Brief Guide to Making it More Meaningful. Dean is a professor of history and philosophy of modern physics at the University of Sydney, where he is also the director of the Sydney Centre for Time. ***Rebroadcast: This episode was recorded on March 22, 2023. 

 Key Takeaways

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In this episode of Perennial Wisdom, my guest is Brittany Polat (co-author of Stoic Ethics: The Basics). In the conversation, we explore the application of Stoicism in relationships, love, and ethics. You can expect to learn the importance of stepping back to gain perspective in relationships, the dichotomy of control in family dynamics, and the concept of indifference in Stoicism. 

Key Takeaways

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In this episode of Perennial Wisdom, I welcome Dr. Brian Russell back to the show. Brian is an author, professor of biblical studies, and transformational coach. He is also the host of Deep Dive Spirituality Conversations, a podcast dedicated to spiritual and missional formation. 

In this conversation, we explore the concept of spiritual formation, the doctrine of original sin, and its implications for understanding Christianity. We also delve into the relationship between virtue and sin, the role of g...

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In this episode of Perennial Wisdom, my guest is Dr. Carl Erik Fisher (author of The Urge: Our History of Addiction). In the conversation, Dr. Fisher, an addiction psychiatrist and bioethicist, shares insights on the multifaceted nature of addiction and its implications on human behavior. Expect to learn the importance of flexibility in psychological health, the need for balance in seeking wisdom, and the cyclical nature of personal growth. To learn more and stay connected, check out: Rat Park wit...

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In this episode of Perennial Wisdom, my guest is Shane Trotter (author of Setting the Bar). In the conversation, Shane and I explore the intersection of character and the common good. We discuss the role of community in character development and the value of adopting timeless virtues. Expect to learn practical approaches to fostering compassion, understanding human limitations, seeking the common good, and much more. Check out Shane’s Substack: Setting the Bar!

Key Takeaways

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In this episode of Perennial Wisdom, my guest Massimo Pigliucci (co-author of the new book Beyond Stoicism) discusses the importance of seeking wisdom beyond Stoicism. We explore the distinctions between virtue and pleasure, the nature of courage, and the interconnectedness of virtues. Prof. Pigliucci explains why we need a balanced approach to happiness, the significance of relationships in leading a meaningful life, and much more. 

Key Takeaways

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In this episode of Perennial Wisdom, my guest is Henry Shukman. Henry is a poet, author, meditation teacher, and co-founder of the single-path meditation app The Way. His most recent books are Original Love: The Four Inns on the Path of Awakening and the Zen memoir One Blade of Grass. He has taught at Google, the New York Times, Harvard Business School and Medical School, and the Institute of American Indian Arts. He has written several award-winning and bestselling boo...

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In this episode of Perennial Wisdom, my guest is James Romm (editor of How to Die and How to Have a Life). In the conversation, James and I discuss the importance of preparing for death, the role of virtue in achieving happiness, and the art of self-reflection. As you’ll hear in the episode, James is highly knowledgeable of Seneca's life and philosophy. He is the author of Dying Every Day: Seneca at the Court of Nero and several other...

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In this episode of Perennial Wisdom, my guest is Donald J. Robertson, author of How to Think Like Socrates. Donald is a psychotherapist, the author of several phenomenal books on Stoic philosophy, and a return guest on the podcast. In this conversation, we discuss the connections between Socrates and Stoicism. We delve into the Socratic method and its relevance in modern cognitive therapy. Donald emphasizes the importance of cognitive flexibility and the practical applications of Socratic techniques in everyday lif...

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In this episode of Perennial Wisdom, my guest is Ken Sheldon, author of Freely Determined. Ken is a psychology researcher and professor; his areas of study are positive psychology, motivation, and well-being. Today, you can expect to learn the complex interplay between free will, determinism, and happiness. The importance of autonomy and the role of personal choices in achieving well-being. Along with the downsides of a deterministic worldview and the significance of mistakes in personal growth. 

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In this episode of Perennial Wisdom, we search for lessons from the life and philosophy of Socrates. Expect to learn the key to simple living, the role of testing your assumptions, and much more. 

📺 Watch on YouTube: https://www.youtube.com/watch?v=JNDsjS8smf0&t=337s

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In this episode of the Perennial Wisdom podcast, we search for insights into the nature of suffering, gratitude, and the good life. Expect to learn why the Buddha said, “Life is suffering,” along with what philosophers and theologians can teach about gratitude and meditating on one’s life.

📺 Watch on YouTube: https://www.youtube.com/watch?v=iaZDnvNAuwQ&t=23s

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In this episode of Perennial Wisdom, we explore the paradoxical lessons on the nature of emotions. Expect to learn why “negative” emotions are not obstacles to the “good” life. The problem with psychological rigidity and the wisdom (and practice) of being open to life. 

📺 Watch on YouTube: https://www.youtube.com/watch?v=WdfQJbusyxA

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In this episode of Perennial Wisdom, I share a short guided contemplation inspired by the Essays of Michel de Montaigne. It's part of a new series on the podcast and the Perennial Meditations YouTube Channel.

📺 Watch on YouTube: https://www.youtube.com/watch?v=uN9pA_P38JE

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In this episode of Perennial Wisdom, we explore the ancient philosophy of pleasure (Epicureanism) to find three lessons for modern living. Expect to learn what the ancient Greek philosopher Epicurus thought about having enough, friendship, and the art of dying well.

📺 Watch on YouTube: https://www.youtube.com/watch?v=D2gLGg4PcN8&t=68s

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