Wisdom 101 Course | The Timeless Art of Leading a Life


The Stoic philosopher Epictetus once said, “How long are you going to wait before you demand the best for yourself?” But what does it actually mean to demand the best for yourself? What is the path to peace, tranquility, or happiness? How does one become a better parent, leader, friend, or anything else? This 5-week course on The Timeless Art of Leading of Life attempts to explore these types of questions.

In a Letter to Menoeceus, Epicurus wrote,

Let no one be slow to seek wisdom when he is young nor weary in the search thereof when he is grown old. For no age is too early or too late for the health of the soul. And to say that the season for studying philosophy has not yet come, or that it is past and gone, is like saying that the season for happiness is not yet or that it is now no more. Therefore, both old and young ought to seek wisdom, the former in order that, as age comes over him, he may be young in good things because of the grace of what has been, and the latter in order that, while he is young, he may at the same time be old, because he has no fear of the things which are to come. So we must exercise ourselves in the things which bring happiness since, if that is present, we have everything, and if that is absent, all our actions are directed toward attaining it.

Are you interested in starting the search for wisdom?

If so, the Perennial Leader Project offers a 5-Week Course called Wisdom 101: The Timeless Art of Leading a Life. The course is facilitated by J.W. Bertolotti, host of In Search of Wisdom (and Perennial Meditations on Substack). Expect to learn timeless perspectives, principles, and practices across philosophical and spiritual traditions to help us live our highest good.

What is wisdom? How does one live a good life? Learn more by clicking the links below to read or listen to specific sections or scroll through to read the entire page. Would you like this course emailed to you over 5-weeks? Sign up below:


I. Overview & Introduction

II. The Wisdom of Impermanence

III. The Wisdom of Connection

IV. The Wisdom of Not Knowing

V. The Cardinal Virtues

VI. The Theological Virtues

VII. The Wisdom of Contemplation

VIII. The Art of Journaling

VIII. The Wisdom of Stillness


The Timeless Art of Leading a Life



1. Perspectives

How are you leading your life?

Do you have a way of making sense of life during good and bad times?

The French philosopher and historian Pierre Hadot described philosophy as a way of life in three parts: metaphysics (how the world works), ethics (or virtues), and practices (or exercises). Here are three universal perspectives across wisdom traditions:

  • Impermanence — The Buddha taught, “All conditioned things are impermanent — when one sees this with wisdom, one turns away from suffering.”

  • Interconnectedness—In Meditations, Marcus Aurelius wrote, “You should meditate often on the connection of all things in the universe and their relationship to each other.”

  • Beginner’s Mind — Shunryu Suzuki wrote in Zen Mind, Beginner’s Mind, “In the beginner’s mind, there are many possibilities, but in the expert’s, there are few.” Although one might also think of humility, wonder, or an openness to learning new things. 

When navigating life — our perspectives (or views and beliefs) shape the principles we put into practice. For example, understanding the nature of impermanence helps us realize that tomorrow is not promised. Or, as Seneca put it, “The future lies in uncertainty; live immediately.”

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2. Principles

When it comes to principles for life, we are wise to adopt a set of time-tested virtues. Plato identified the four cardinal virtues with the character of a good city as described in The Republic. According to Plato, “Clearly, then, it will be wise, brave, temperate, and just.” The cardinal virtues of courage, temperance, justice, and wisdom are four near-universal principles adopted by Christianity and most of Western philosophy.

Although the term virtue can feel outdated or old-fashioned, it is relevant and practical. Virtue (or arete) translates as excellence or moral virtue. One could think of virtue as living up to one’s full potential or the highest good.

  • Courage — In Nicomachean Ethics, Aristotle observed, “Our aim is not to know what courage is but to be courageous; not to know what justice is but to be just.” When thinking of virtue, we must view virtue as action.

  • Temperance —Think of temperance as moderation or simply self-control. The Stoic philosopher Musonius Rufus suggested, “If we were to measure what is good by how much pleasure it brings, nothing would be better than self-control.”

  • Justice — The virtue of justice is described as fairness and kindness. The novelist Henry James put it this way, “Three things in human life are important: the first is to be kind; the second is to be kind, and the third is to be kind.”

  • Wisdom — Socrates transformed our understanding of wisdom. It is not just a matter of having skills, knowledge, or a long life of experience. It is realizing how little you understand about yourself, others, and the world around you.

Our principles help us to navigate life; one could think of them as points on a compass. The nineteenth-century philosopher Soren Kierkegaard believed the most important thing was to find a truth to live by. Seneca urged Lucilius, “Adopt once and for all a single rule to live by, and make your whole life conform to it.” The principles we choose set our direction and help us to be intentional about leading our life.

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3. Practices

When it comes to practices (or exercises), there are many to choose from across wisdom traditions. Think of practices like meditation, journaling, prayer, memento mori, and many others. 

Here are three from both philosophical and spiritual traditions: 

  • Meditation — “The practice of meditation teaches us how to relate to life directly,” explains the teacher and writer Pema Chödrön, “so we can truly experience the present moment, free from conceptual overlay.”

  • Journaling — The practice of journaling enables us to examine our day in an objective and non-judgmental way. In On Anger, Seneca put it this way, “When the lamp is taken out of my sight…, I pass the whole day in review before myself, and repeat all that I have said and done.”

  • Contemplation — Aristotle said, “contemplation is the highest activity of human life.” Similarly, the theologian Meister Eckhart suggested, “What we plant in the soil of contemplation, we shall reap in the harvest of action.”

Although much more is to be said about the timeless art of leading a life, it starts with creating (or adopting) a philosophy to lead your life. The art of living involves thinking about how you see (perspectives), how you live (principles), and what you do (practices) to lead your life.


The Wisdom of Impermanence


The notion of impermanence (or nothing lasts) is stressed across wisdom traditions. It is often viewed as a foundational perspective or universal truth. Although it seems we can often overestimate our understanding of impermanence.

A philosophy of life has three components: metaphysics (how the world works), ethics (or virtues), and a set of exercises or practices. However, most of us spend more time and effort on ethics and practices than on shaping our perceptions (or views and beliefs) about the world.

But people like the ancient pre-Socratic philosopher Heraclitus (and the Buddha) stressed that understanding “nothing endures but change” is central to living a good life. Heraclitus called “change” the only constant thing, emphasizing that everything flows, and nothing abides; everything gives way, and nothing stays fixed.

Similarly, Marcus Aurelius wrote this to himself in Meditations:

Is change something to fear? But can anything happen without change? Is there anything that’s nearer and dearer to universal nature? What about you personally? Can you take a warm bath unless the firewood undergoes a change? Can you be nourished unless your food undergoes a change? Can anything else worthwhile take place without change? So don’t you see that the changes you experience are no different and are similarly necessary to universal nature?

One of my favorite quotes of all time comes from the pre-Socratic philosopher Heraclitus: “No one ever steps in the same river twice, for it is not the same river, and they are not the same person.” But how many of us actually see ourselves as constantly changing? Are you making decisions as the person you are today (or a past version of yourself)?

The Buddha stressed, “One moment can change a day; one day can change a life.” In truth, the past and future have little to do with the direction we choose and the choices we make now. But it is not only Heraclitus and the Buddha stressing this point. The Existentialists also urge us to realize that we are constantly becoming.

My conversation with Skye Cleary (the author of How to Be Authentic) discussed how Simone de Beauvoir’s philosophy and the notion of becoming. Cleary writes,

For Beauvoir, there is no fixed essence to our being since we are always becoming something other than what we are today. ‘Existence precedes essence,’ meaning that we exist first and then spend the rest of our lives creating who we are (our essence).

To quote Heraclitus a final time, “The sun is new every day.” Each day (and moment) is an opportunity to begin again. The wisdom of impermanence is about understanding that nothing lasts. We are perpetually dying every day and becoming every day.

Additional Resources:


The Wisdom of Connection



Pierre Hadot observed that philosophy deepens and transforms habitual perception, forcing us to become aware that we perceive the world. Therefore, one must ask themselves whether or not they are perceiving the world accurately. The notion of interconnectedness appears throughout many philosophical and spiritual traditions.

In his Meditations, Marcus Aurelius put it this way,

In a way, all things are interwoven and therefore have a family feeling for each other: one thing follows another in due order through the tension of movement, the common spirit inspiring them, and the unity of all beings.

Marcus Aurelius advised himself to “meditate often on the connection of all things.” And in many passages throughout Meditations, he utilizes the wisdom of connection to act with kindness and virtue. In a well-known passage on dealing with difficult people, he concluded, “None of them can harm me, …, nor can I become angry with someone who’s related to me, or hate him, because we were born to work together, like feet or hands or eyelids, like the rows of upper and lower teeth.”

Similarly, the idea of connection aids us in answering perennial questions. The late Zen Master Thich Nhat Hanh suggested when we ask ourselves honestly the question — Who am I? If we have enough time and patience, it reveals some universal truths.

In his classic book Silence, Hanh wrote,

You may see that you’re made of elements, like water for example. If you remove the water from you, there’s no “you” left. You’re made of earth. If you remove the element earth from you, there’s no “you” left. You’re made of air. You need air desperately; without air, you cannot survive…

The Stoics utilized a visual known as Hierocles’ circles or oikeiôsis (see below) to practice the wisdom of connection. The objective is to draw further circles inward, treating our family as ourselves, friends as family, and so on, until ultimately, the entire human race.

​According to Hierocles’ circles,

For, in short, each of us is, as it were, circumscribed by many circles; some of which are less, but others larger, and some comprehend, but others are comprehended, according to the different and unequal habitudes with respect to each other. For the first, indeed, and the most proximate circle is that which everyone describes his own mind as a center, in which circle the body, and whatever is assumed for the sake of the body, are comprehended. For this is nearly the smallest circle, and almost touches the center itself. The second from this, which is at a greater distance from the center, but comprehends the first circle, is how parents, brothers, wife, and children are arranged. […]

Ancient Circles for Modern Living

Across the more than one hundred interviews conducted on In Search of Wisdom, several guests have raised concerns about the epidemic of loneliness. But if wisdom traditions point to the truth of interconnectedness.

Why do so many of us experience loneliness?

In his book Together, Vivek H. Murthy (21st Surgeon General) described loneliness this way,

Loneliness is the subjective feeling that you’re lacking the social connections you need. It can feel like being stranded, abandoned, or cut off from the people with whom you belong — even if you’re surrounded by other people. What’s missing when you’re lonely is the feeling of closeness, trust, and the affection of genuine friends, loved ones, and community.

We have lost (or forgotten) the ancient wisdom of seeing ourselves as interconnected. I imagine (like me) many of you did not learn about Hierocles’ Circles or “meditating often on our interconnectedness.” As legend has it, when Diogenes the Cynic was asked where he came from, he responded with one word: kosmopolites, meaning “a citizen of the world.” The cosmopolitan view (by the Cynics and Stoics) urges us to recognize all human beings equal and unconditional worth, a worth grounded in moral choice capacity rather than on traits that depend on fortuitous natural or social arrangements.

Marcus Aurelius used the analogy of a branch to stress the need to remain connected to the whole community. Marcus wrote,

A branch cut from its neighboring branch is necessarily cut away from the whole tree. In the same way, a human being severed from just one other human has dropped from the whole community. Now the branch is cut off by someone else, but a man separates himself from his neighbor by his hatred or rejection, not realizing that he has thereby severed himself from the wider society of fellow citizens. […]

Final Thoughts

My interview with Nancy Sherman (author of Stoic Wisdom) revealed that the roots of interconnectedness in Stoicism run just as deep as those of self-reliance. We have much to learn from the ancients and mistakes to avoid, says Sherman. Wisdom can help unite us to face our individual and shared challenges. “But only when empathy and mercy course through the veins of reason.”

Contemporary life makes it easy to forget that we are connected. A certain degree of wisdom is required to see and experience our connection.

But as Seneca stressed, “No one ever became wise merely by chance.” The wisdom of connection must be sought after — even Marcus Aurelius had to embark on the search. He had to cultivate and “meditate on the connection of all things.” Marcus Aurelius worked to expand his circles; therefore, we are wise to work to expand (and realize) our circles of connection.

Additional Resources:


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