The Stoic art of teaching from the edge of your understanding
Teaching from what you most need to learn
There is an interesting and peculiar irony in our path to develop mastery, and that is the wisdom we are most eager to share with others is often born from a place of our internal struggle.
When I find myself pushing the importance of patience in leadership, it’s usually after an event, or a week, where my patience has been tested. This, though isn’t a coincidence, the Stoics recognized this long ago.
Seneca, writing to his friend Lucilius, said, “docendo discimus” — while we teach, we learn. This thought and deep insight wasn’t just a wise philosophical conjecture but an understanding the Stoics had, which was that our knowledge becomes cemented through passing it on to others.
The Paradox of Teaching What We Haven’t Mastered
Many of us are bound by the thought that we can only teach something that we are the formidable most expert in. Yet, history reveals something completely different. The most transformative teachers are often those who are still wrestling with the very principles they are trying to share.
Consider Marcus Aurelius, emperor of Rome and perhaps history’s most influential Stoic. His Meditations was never intended for others consumption. These writings were his personal reminders, his journey, and reflections of a man struggling to embody the virtues he believed were so essential. In one entry, he writes to himself: “Begin each day by telling yourself: Today I shall be meeting with interference, ingratitude, insolence, disloyalty, ill-will, and selfishness.” This wasn’t just the insight of someone who had conquered these challenges, but it was someone preparing himself so he would be ready to face them when they showed up.
Last month, I found myself mentoring a manager they were overwhelmed by the unexpected delays and setbacks they were facing. As I coached them through it and discussed the principles of resilience and perspective, I realized I was also reinforcing lessons I needed in my leadership. The very act of explaining how to distinguish between controllable and uncontrollable factors and events helped me reclarify my thoughts about how I need to approach work and challenges.
The Protégé Effect
What the Stoics understood through the experiences they gained in life, cognitive science has confirmed through rigorous studies. Researchers have identified the “protégé effect,” a phenomenon where teaching others enhances the teacher’s understanding and retention of the material.
When we teach, several powerful cognitive processes activate simultaneously:
First, we must organize the information coherently so we can share it, which requires a deeper processing of the material than passively learning it. Second, we anticipate questions and objections others will have, forcing us to examine the concepts from different angles and perspectives so we can explain them. Finally, we translate the ideas into conversation, which demands our deep, genuine understanding rather than just being familiar with it.
A colleague once said that she never truly understood strategic planning until she had to explain it to new hires she was onboarding. “Having to break it down for someone else,” she said, “made me realize which parts I’d been skimming over in my own thinking.”
Stoic Wisdom, Modern Practice
The Stoics weren’t just philosophers; they were practical, and they were, in a sense, psychologists who recognized that knowledge without application remains hollow, it’s the practical application that mattered most. Epictetus, who began life as a slave before becoming one of Rome’s most respected teachers, emphasized that philosophy was not about impressing others with fancy rhetoric or clever arguments but about transforming your character through daily practice.
This perspective offers great insights into both leadership and personal development:
When you struggle with your own emotional regulation, coach or guide someone else through how to manage through those difficult feelings. When strategic thinking challenges you, mentor a team member on developing long-term planning skills. The lessons you most need to improve or integrate are in fact those you should be sharing.
The Teaching-Learning Cycle
How might we become more purposeful and apply this Stoic insight? Several approaches have proven particularly effective:
Begin from a place of imperfection. The most authentic teaching comes not from being perfect but from a place of honesty and engagement with pursuing growth. Last year, I shared my framework for decision-making with my team while I was still acknowledging the areas where I was still refining my approach. This transparency created the space for collaborative learning discussion rather than preaching from a place of expertise.
Document your developmental edge. Following Marcus Aurelius’s example, maintain a leadership journal where you document your areas of struggle along with your areas of success. These reflections will often give you the most valuable insights that you will be able to share with others.
Teach through dialogue rather than monologue. The Socratic tradition that heavily influenced Stoicism emphasized questions over declarations. When mentoring others, approach conversations with genuine curiosity. Ask, “What challenges your resilience most?” rather than simply prescribing techniques to become more resilient.
Create teaching opportunities. Don’t wait for the right, perfect formal occasion to share something. Brief team discussions, thoughtful questions during meetings, and spontaneous conversations can all provide platforms for mutual learning.
Overcoming Barriers to Teaching While Learning
Even understanding the benefit we get from teaching what we often need, we still hesitate to go down that path and teach what we haven’t mastered. Three common roadblocks come up here:
Imposter syndrome- yes, that voice that whispers that we don’t have the knowledge, we’re not enough. Epictetus would remind us that wisdom begins with first acknowledging our limitations. Your vulnerability in admitting what you’re still learning can create an authentic connection with those you teach.
Fear of contradiction suggests that being wrong takes away from our credibility. The Stoics would argue the opposite: intellectual flexibility strengthens us rather than weakening our authority. When I’ve acknowledged errors in my thinking by trying to be less wrong, team trust will deepen.
Time constraints seem to preclude teaching opportunities. Yet teaching, even in burst, does not have to be formal or time-intensive. Even brief reflections shared during team meetings can initiate powerful learning and discussions.
The Spiral of Growth
The Stoic approach isn’t linear but cyclical. We learn, we teach, we discover gaps in our thinking or understanding, we refine our knowledge, and we teach again, and each cycle will deepen our wisdom.
Zeno, the founder of Stoicism, began not as a teacher but as a student who lost everything in a shipwreck. His quest for wisdom led him to share his developing philosophy with others beneath the painted porch (the stoa poikilē) in Athens. From personal catastrophe emerged teachings that would influence Western thought for millennia.
Our journeys follow similar patterns. The leadership principles we struggle to consistently apply become the insights we often most passionately share. The practices or tools to regulate emotions we practice imperfectly become the coaching we offer to others facing similar challenges.
In embracing this paradox — that we teach best what we most need to learn — we discover a growth path that is both humbler and more powerful than the pursuit of expertise alone. We recognize that mastery comes not from arriving at a destination but from committed practice shared openly with others.
What principle or knowledge area are you currently working to embody or learn? Perhaps that’s precisely what you should be teaching.