Perennial Wisdom
Perennial Wisdom is a podcast for seekers and curious minds. Each episode explores philosophical and spiritual traditions for universal truths and enduring ideas to help you (and me) never stop learning how to live.
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The Art of Thinking—From Socrates to St. Augustine
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 episode offers a quiet, contemplative space for anyone overwhelmed by others' opinions and eager to reconnect with their own thoughts.
Key Takeaways
Why Socrates tied thinking to moral courage
How Augustine turned thinking into a form of prayer
The difference between reacting and reflecting
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Episode Transcript
The following is a transcript from “The Art of Thinking—From Socrates to St. Augustine” on the Perennial Wisdom podcast (Ep. 253).
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There is a kind of thinking that happens on the surface of life—reactive, anxious, hurried. And then there is another kind of thinking, deeper and quieter, where the soul begins to speak.
Socrates called it an examination.
St. Augustine called it inwardness.
Both called it a necessity for a life of truth.
This meditation is an invitation to descend—to move from noise to knowledge, from distraction to discernment.
1. Socrates and the Courage to Question
Imagine waking up one morning and realizing that most of your thoughts aren’t actually yours. They’re borrowed—absorbed from headlines, inherited from family, echoed from friends, and shaped by algorithms.
We scroll, we react, we repeat…
But do we think? That is the question.
Long before smartphones and noise, Socrates, in the streets of Athens, warned us about this danger. He insisted that freedom—real freedom—begins when we learn to think for ourselves.
Socrates, barefoot in the marketplace, asked the questions everyone else avoided. “What is justice?” “What is virtue?” “What is good?”
But he didn’t teach answers—he taught inquiry. His wisdom started with a humble admission: “All that I know is that I know nothing.”
His confession was not despair but liberation. For Socrates, to think was to awaken—to strip away illusion until only what is real remains.
When accused of corrupting the youth and sentenced to death, he did not retreat.
He told his accusers:
A man who is good for anything ought not to calculate the chance of living or dying; he ought only to consider whether in doing anything he is doing right or wrong. — Plato, Apology
Philosophy, for Socrates, was not about cleverness. It was about conscience—the daily practice of aligning one’s reason with what is just.
2. St. Augustine and the Journey Within
Centuries later, during a time when Rome was collapsing, another restless mind responded to the same call—but turned it inward. St. Augustine picked up where Socrates left off: recognizing that truth must be sought, but that the search leads not outward, but inward.
In his Confessions, he stressed,
And men go abroad to admire the heights of mountains, the mighty waves of the sea, the broad tides of rivers, the compass of the ocean, and the circuits of the stars, yet pass over the mystery of themselves without a thought.
St. Augustine’s life was a whirl of desire, doubt, and ambition. He studied the philosophies of his time, mastered rhetoric, and tasted every pleasure—and yet, he remained restless.
“Our hearts are restless until they rest in Thee,” he wrote.
The American philosopher James Miller described it this way in Examined Lives,
The quest for wisdom can be wayward, and a wise man cannot live by reason alone. These are two of the morals that one might draw from Augustine’s own account of the first half of his life in his Confessions. … In the story he tells in the Confessions, Augustine was forever trying to find the truth, the one and only way of life that might make a man perfectly happy.
St. Augustine came to realize that thinking was not just an abstraction; it was an act of confession. It involved confronting not only ideas but also motives, not only truth but self-deception.
He stressed:
Do not go outward; return within yourself. In the inward man dwells truth. And if you find that your nature is changeable, transcend yourself.
To think for yourself, St. Augustine believed, is to wake up to the light within—to discover that the act of attention is itself a form of prayer.
3. The Rhetoric of Freedom
To think for yourself is to engage in this inner rhetoric—the dialogue between belief and evidence, between passion and conscience.
Aristotle called it logos, the reasoned order that brings harmony between word and world. Jay Heinrichs, in his new book Aristotle’s Guide to Self-Persuasion, puts it this way:
Aristotle argued that any significant change in our lives, bad or good, constitutes a soul test. Bad news, good news: Stuff happens. Your response determines what kind of soul you have, and how much you live up to that soul.
Heinrichs continues,
Aristotle wrote that the secret of the good life, the happiest life, is to be as human as humanly possible. This meant aligning oneself with one’s noble and virtuous soul. … That is how we free ourselves from fears, lack of motivation, and bad habits. And our masterful use of words—with ourselves as well as with one another—leads to self-mastery.
Before we can persuade others, we must learn to persuade ourselves—not with slogans, but with sincerity; not with emotion, but with evidence. Aristotle emphasized that the challenge was not one of vanity, but of virtue.
The Modern Challenge
Thinking for yourself in the twenty-first century doesn’t mean escaping society—it means seeing through it. It means pausing before you repost. It means questioning what outrages you and asking why. It means trusting your conscience more than your feed.
Algorithms amplify what flatters us.
Philosophy asks what humbles us.
Socrates cautioned Athens about the crowd's susceptibility to deception. St. Augustine warned Christendom that the self is easily fooled.
Both were right—and both called us back to humility, the ground of freedom.
4. The Art of Inner Freedom
For both thinkers, the mind is not a machine—it is a mirror of the soul. Socrates turned reason into a moral act. St. Augustine turned confession into an act of truth.
In The Inner Experience, American Trappist monk Thomas Merton echoed this sentiment when he wrote:
Penetration into the depths of our being is, then, a matter of liberation from the ordinary flow of conscious and half-conscious sense impressions, but also and more definitely from the unconscious drives and the clamoring of inordinate passion.
Merton adds,
Freedom to enter the inner sanctuary of our being is denied to those who are held back by dependence on self-gratification and sense satisfaction, whether it be a matter of pleasure seeking, love of comfort, or proneness to anger, self-assertion, pride, vanity, greed, and all the rest.
Thinking for yourself involves resisting that temptation—transcending borrowed beliefs, avoiding our lower desires, and overcoming fear.
It is not rebellion but reverence.
For Socrates, being free meant being guided by the best part of ourselves. When the rational part leads, and the spirited and pleasure-seeking senses follow, a person is in control of himself rather than a slave to his desires. This harmony is justice within the soul—and this harmony is freedom.
Final Thoughts
Between Socrates and St. Augustine lies the story of human freedom. One taught us how to question; the other taught us how to listen. Both believed that truth is not a possession but a presence—something we enter, not something we own.
Toward the end of his Confessions, St Augustine observed,
I have loved You late, O Beauty that is always old and always new. You were within me, but I was outside, searching for You.
It’s important to remember that thinking for yourself doesn’t mean walking alone—it means walking consciously, aware of the divine reason that animates everything.
Ultimately, thinking for yourself isn’t about rebellion; it’s about respecting who you are. When you trust (and train) your own mind, you’re celebrating your true self and the wisdom inside you.
Reflection Exercise
For anyone interested in further reflection, I encourage you to consider these questions:
(1) What beliefs or opinions have you accepted without truly examining?
(2) When was the last time you were still enough to hear your own thoughts?
(3) What might it mean for you to seek truth not just with your mind, but with your soul?
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Thank you for reading/listening; I hope you found something useful.
Until next time, be wise and be well.
J.W.
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