Stoicism’s Lessons on Becoming Wise - Ryan Holiday

An illustrative story from his recent talk in Kentucky paints this vividly: after a series of travel delays and a mix-up with slide presentations, Ryan was forced to deliver a 45-minute talk sans visuals, in front of a live band improvising. Rather than succumbing to frustration, he leaned into the challenge and discovered fresh insights emerged. This experience reinforced a core lesson—while preparation is necessary, the ability to perform amidst chaos is invaluable. It connects deeply with Stoic ideas about control and perception: we must accept external disruptions while controlling our response.

Censorship

The conversation takes a serious turn as Ryan recounts his recent experience with the Naval Academy. Over four years, he has given a lecture series on cardinal virtues to incoming cadets, culminating in a planned talk on wisdom. However, just before the event, the Academy requested he omit critiques of their decision to purge hundreds of books from their library—books addressing diversity, history, and difficult social issues. This censorship, imposed under political directives targeting "wokeness," challenged Ryan's ethical boundaries.

He explains how confronting this censorship highlighted the paradox of ethics in power structures. The Naval Academy, tasked with cultivating ethical leaders who must think independently and challenge authority, was simultaneously suppressing difficult truths. Ryan chose to withdraw rather than compromise his message. The refusal to engage with uncomfortable ideas endangers intellectual vitality. The incident exemplifies how restriction of ideas not only undermines education but also degrades leadership—especially in institutions responsible for wielding great power.

Wisdom as an Evolving Virtue

Ryan delves into the enigma of wisdom—a virtue notoriously difficult to define or claim. Unlike courage or discipline, wisdom is multifaceted, blending knowledge, experience, creativity, insight, and humility. Importantly, wisdom resists possession; the more one learns, the more one recognizes their ignorance. Wisdom is described as a horizon that expands with every step taken, perpetually out of reach though always guiding.

This ongoing quest requires humility, a recognition Ryan stresses repeatedly. The paradox of wisdom is that those who claim it most loudly almost certainly lack it. True wisdom comes with an openness to continuous learning—a "learn, apply, repeat" cycle that integrates intellectual understanding with lived experience. Wisdom is never static; it demands a humble acceptance that knowledge is infinite and that growth is a lifelong endeavor.

Challenges of AI and Shortcut Culture

In a modern world obsessed with "life hacks" and shortcuts, Ryan offers a counterpoint anchored in patience and persistent effort. He critiques the allure of quick fixes, such as expecting artificial intelligence to deliver comprehensive wisdom without the groundwork of critical thinking. While tools like AI offer vast knowledge, they do not replace the necessity of discernment—knowing what questions to ask, sifting good answers from falsehoods, and applying insights wisely.

He warns against the seductive illusion that knowledge can be downloaded or superficially absorbed. Mimicking wisdom through memorization or regurgitation is insufficient. Instead, wisdom requires deep assimilation, the ability to transfer abstract concepts into concrete actions and ethical decisions. This perspective encourages embracing the discomfort of hard work over the false ease of quick solutions.

Historical Narratives

Ryan reflects on the role of history and storytelling in transmitting wisdom. He distinguishes between literal historical fact and the deeper figurative truths conveyed by myths and biographies. Stories like that of the Roman general Cato (Catis) or George Washington's resignation exemplify ideals of restraint, sacrifice, and service rather than precise factual recounting.

Such narratives serve as "portable stories" or "aphorisms," compact lessons that anchor moral and philosophical reflection. While historians seek objective truth, Ryan notes that most people benefit more from the lessons and values these stories embody. Ancient tales act as scaffolding, helping individuals frame their experiences and decisions in alignment with enduring human virtues.

Balancing Tradition and Innovation

A nuanced discussion arises about the tension between innovation and respect for tradition. Ryan underscores the necessity to understand why systems and institutions exist before attempting to overhaul them. Using examples like the Wright brothers and abolitionists Abraham Lincoln and Thomas Clarkson, he illustrates how effective reformers combine fresh perspectives with deep study of existing structures.

True wisdom requires negative capability: holding seemingly contradictory ideas simultaneously. Innovators must remain open to questioning the status quo while empathetically grasping the historical and practical reasons behind it. This balance prevents hubris and rash disruptions, allowing for change grounded in understanding and strategic empathy.

Emotional Regulation and Stoic Practice

Emotional regulation emerges as a cornerstone of wisdom and effective living. Ryan stresses that Stoicism is not about suppressing emotions but mastering their influence. Recognizing feelings like anger, envy, or anxiety without impulsive reaction is a skill honed over time, akin to physical training.

The metaphor of exercise resonates: just as muscles strengthen through repeated practice, emotional discipline grows through intentionally choosing responses. Ryan reveals that part of his own discipline involves deciding what to think about and when, deliberately setting boundaries to prevent anxiety and distraction. Emotional regulation fosters equanimity, enabling clarity and resilience amid life's chaos.

Wisdom's Relationship with Intelligence and Ego

Ryan explores the pitfalls highly intelligent people face in developing wisdom. Intelligence, while valuable, can be undermined by ego, complacency, and closed-mindedness. A common mistake of the clever is mistaking knowledge accumulation for wisdom or falling into the trap of overconfidence.

He articulates how ego distorts perception, making individuals resistant to new learning or input that challenges their identity. Moreover, smart people often neglect emotional growth, leaving unresolved childhood wounds or vulnerabilities unaddressed. In contrast, true wisdom entails humility and ongoing self-examination, dismantling biases and blind spots.

The Cost of Wisdom

The guest acknowledges that acquiring wisdom is not without its burdens. Awareness and knowledge invite self-consciousness and sometimes cynicism. Excessive rumination can paralyze action, and hard-earned wisdom may breed a certain jadedness if not tempered by hope and purpose.

Ryan emphasizes the need to guard against becoming hardened or disconnected by wisdom's weight. Instead, the wise must learn to balance critical insight with wonder and optimism, preserving the joy of discovery alongside skeptical rigor. This balance sustains engagement with the world rather than retreat from it.

Recognizing Unteachable Lessons

One profound theme is the concept of "unteachable" lessons—truths that individuals cannot learn secondhand but only through personal experience. Ryan cites examples like realizing "money won't make you happy" or the ephemeral nature of fame. Though commonly spoken, these lessons remain transformative precisely because they require lived understanding.

The process involves ongoing cycles of reading, reflection, and direct experience. Knowledge without corresponding life experience is incomplete. Wisdom, therefore, emerges at the intersection of ideas and practice, weaving intellectual grasp with emotional insight over time.

Wrestling with Contradictory Reality

Ryan discusses the idea of "negative capability," the capacity to entertain conflicting truths without premature resolution. He notes how this ability underpins wise leadership and nuanced thinking, allowing one to hold empathy for opposing views while maintaining core values.

Examples from history and philosophy reinforce this idea: understanding why people believe what they do, even if fundamentally flawed, enables effective dialogue and strategy. The wise person accepts complexity, eschewing simplistic answers in favor of thoughtful humility and comprehensive perspective.

Sustained Effort, Discipline, and Presence

Throughout the conversation, Ryan continually returns to the centrality of sustained discipline and presence in the cultivation of wisdom. He reflects on his own creative process, explaining that for him, joy is found in the work itself rather than external accolades. Achievements are milestones, not end points.

He highlights the importance of being fully engaged in the present moment—whether swimming, writing, or delivering a talk—rather than consumed by outcomes or vain celebrations. This mindfulness aligns with Stoic precepts, fostering resilience and focus amid uncertainty. Ultimately, wisdom is a practice of presence as much as insight.