Chapter 1: The Courage of Alexander the Great

Learning from the Lives of Great Men

More than two thousand years ago, a Greek historian named Plutarch set out to capture the essence of leadership, virtue, and human character in a monumental work known as Lives of the Noble Greeks and Romans — or simply Plutarch’s Lives. His purpose was simple yet profound: to chronicle the achievements and moral struggles of the greatest figures in history, not merely to record events, but to reflect on the qualities that made these men worthy of admiration—or sometimes, caution.

Plutarch wasn’t just interested in recounting battles won, empires built, or power seized. His focus was the character of these men—their courage, ambition, wisdom, flaws, and failures. He believed that by studying their lives, we could uncover timeless lessons about what it means to live well, lead wisely, and face challenges with integrity.

Though the world has changed immeasurably since the days of Caesar, Alexander the Great, and Marcus Aurelius, the human condition remains much the same. The same questions men asked back then—about how to lead with honor, how to handle adversity, and how to balance ambition with morality—are questions we ask today. Technology may have evolved, societies may have transformed, but the core principles that make a man of character have remained unchanged.

Of course, these men were very much a product of their time. The cultural, political, and social landscapes they navigated were drastically different from ours. But what makes their stories invaluable is that they reveal universal truths about human nature—truths that transcend the centuries.

Their triumphs show us the power of courage, determination, and vision. Their mistakes reveal the dangers of unchecked ambition, arrogance, or moral compromise. Their lives offer us a blueprint—not just for success in the world, but for personal growth, leadership, and the cultivation of inner strength.

This book, How a Man Should Live, distills those ancient lessons for the modern man. In our rapidly changing world, men face new pressures to conform, succeed, and lead, often without a clear sense of what those words really mean. By revisiting the lives of history’s greatest leaders, thinkers, and warriors, we can find clarity on what truly matters. These men faced their own trials, and their responses still hold relevance today.

We are not building empires or marching to war in the same way they did, but the battles we fight—in our careers, families, and within ourselves—are no less significant. And the virtues that shaped these ancient leaders—strength, integrity, resilience, humility—are the same virtues that can shape the lives of men today.

In each chapter, we will explore the life of a different leader or thinker from Plutarch’s writings, breaking down the key lessons from their triumphs and failures. But this book isn’t just a history lesson. It’s a guide, meant to be lived. Every chapter will provide practical exercises so that you can take these ancient lessons and apply them directly to your own life—building the foundation for strength, character, and purpose in the modern world.

The question is no longer just, “How did these great men live?” but “How should a man live today?”

Let’s begin.

The wind whipped across the plains of Issus, a biting chill that mirrored the fear gnawing at the hearts of the Persian soldiers. Before them, a phalanx of Macedonians, a tide of bronze and steel, held their ground. At the head, a young man, barely more than a boy, surveyed the vast battlefield with eyes that held not terror, but a fierce, unwavering light. This was Alexander, not yet thirty, facing an army ten times his size, yet his gaze held the quiet certainty of a man who knew, deep in his bones, that he would prevail. His courage, a shimmering flame in the heart of the storm, wasn't a reckless abandon, but a calculated risk, a leap of faith fueled by unwavering belief in himself and his men. It was a courage born not of bravado, but of a profound understanding of the stakes.

Plutarch, chronicler of lives both grand and ordinary, paints a portrait of Alexander not as a mythical demigod, but as a man of flesh and blood, a man consumed by ambition, yet driven by a relentless pursuit of excellence. His courage wasn't confined to the battlefield; it was the bedrock of his character, the force that propelled him to conquer not just empires, but his own limitations. He faced down not only armies, but also the insidious whispers of doubt, the gnawing anxieties that plague even the most resolute among us. His relentless pursuit of knowledge, his willingness to learn from others, even his enemies, speaks to a courage that extended beyond physical prowess, a courage that demanded intellectual humility and a constant striving for self-improvement. This is the courage that resonates most powerfully today, a courage that transcends the clash of swords and shields, a courage that demands we confront our own inner battles, our own personal Gordian knots.

Consider the Granicus River, a seemingly insignificant waterway that became a crucible of courage. Alexander, facing a vastly superior force, plunged into the icy waters, leading his men into the heart of the enemy. The image is stark, brutal, yet breathtaking in its audacity. It wasn't a foolhardy charge, but a calculated gamble, a strategic maneuver born of courage and an understanding of the psychology of war. He understood that true leadership lies not in commanding from afar, but in sharing the risks, in bearing the brunt of the battle alongside those he led. This is a lesson lost on few, yet often forgotten. In our modern world, where leadership often hides behind screens and sanitized reports, Alexander's example serves as a stark reminder that true leadership demands vulnerability, a willingness to stand shoulder to shoulder with those we serve, to share in their struggles and triumphs.

The courage to lead isn't about grand pronouncements or sweeping gestures. It's about the quiet determination to face the day, to confront the challenges that life inevitably throws our way. It's about the small acts of bravery, the daily choices that demand we step outside our comfort zones, that push us beyond the familiar and into the unknown. It's the courage to speak truth to power, to stand up for what we believe in, even when it means facing ridicule or opposition. It's the courage to admit our mistakes, to learn from our failures, and to rise again, stronger and wiser. It's the courage to love deeply, to risk vulnerability, and to embrace the uncertainties of life with open arms. It's the courage to be fully ourselves, flaws and all, and to live a life of purpose and meaning.

The wind still whispers across the plains of Issus, carrying with it the echoes of Alexander's courage. And as we listen, we hear not just the clash of swords, but the quiet, persistent beat of a heart that dared to dream, to strive, to conquer, not just the world, but himself. What small act of courage will you embrace today? What fear will you confront? What battle will you choose to fight?

“I am not afraid of an army of lions led by a sheep; I am afraid of an army of sheep led by a lion.” - Alexander the Great

Son of Philip, heir to a legacy forged in ambition and bloodshed, Alexander learned early the intoxicating scent of power, the bitter taste of betrayal. His tutor, Aristotle, instilled in him not just the classics, but a thirst for knowledge that mirrored his father's insatiable hunger for conquest. Yet, even in the shadow of such towering figures, a distinct spark ignited within him – a restless energy, a yearning to surpass all that came before. This was not merely the ambition of a king; it was the burning heart of a myth in the making.

His conquests were a whirlwind, a relentless storm across the known world. Persia fell before him, not just to the honed edge of his phalanx, but to the sheer force of his will, a will that seemed to bend the very fabric of reality to his desires. He rode into battle, a figure sculpted from sun-drenched bronze, his laughter echoing amidst the clash of steel. But the echoes of those victories, the whispers of his triumphs, were often drowned out by the screams of the vanquished, the silent lament of shattered lives. The tapestry of his empire, so brilliantly woven with threads of glory, was stained with the darker hues of brutality and bloodshed.

He sought not just dominion over lands, but over the very definition of greatness. His relationship with Hephaestion, a bond deeper than brotherhood, was a mirror reflecting his own internal struggles – the yearning for connection, the desperate need for love amidst the isolating heights of power. Their shared journey, a testament to the enduring power of human connection, was also a stark reminder of the fragility of life, the bitter sting of loss that even a king could not escape.

Alexander’s death, young and sudden, cast a long shadow over his empire. Did his ambition ultimately consume him, leaving behind a legacy more defined by its unfinished nature than its vast scope? Or did his relentless pursuit of greatness, despite its flaws, leave an indelible mark on the world, a testament to the boundless capacity of the human spirit to dream, to conquer, to create, and ultimately, to fall? The answer, perhaps, lies not in the sweeping grandeur of his conquests, but in the quiet reflection on the enduring questions of mortality and legacy that his life continues to evoke. The echoes of his name, a whisper across the centuries, remind us that even the most dazzling flames eventually fade, leaving behind only the embers of memory, and the enduring questions they ignite within us.

Plutarch portrays Alexander's courage, not as reckless bravado, but as a multifaceted virtue rooted in self-awareness, strategic thinking, and a commitment to personal growth. This isn't just about battlefield bravery; it's about the courage to confront our inner demons, to pursue excellence, and to lead authentically. In today's world, where pressures to conform and anxieties are rampant, understanding and cultivating this type of courage is paramount for men's well-being.

The nuances of courage are often misunderstood. It's not the absence of fear, but the willingness to act despite it. It's about facing challenges, even when the outcome is uncertain, and accepting vulnerability as a necessary component of leadership and genuine connection. Modern society often equates success with invulnerability, creating a culture where men feel pressured to suppress their emotions and avoid showing weakness. This can lead to isolation, mental health struggles, and strained relationships. The truth is, courage requires acknowledging our fears and insecurities, and acting in spite of them.

The impact of courage (or its absence) on men is profound. Without it, men may struggle to assert their needs in relationships, leading to resentment and disconnection. In their careers, a lack of courage can hinder ambition and prevent them from taking risks necessary for growth. The pressure to conform to rigid masculine ideals can severely impact mental health, leading to depression, anxiety, and substance abuse. Conversely, courageous men are better equipped to navigate challenges, build healthy relationships based on authenticity, and pursue their goals with resilience. They are more likely to seek help when needed, fostering a stronger sense of self-worth and overall well-being.

Contemporary psychology emphasizes the importance of emotional intelligence and self-compassion in building resilience. Research shows that men who embrace vulnerability and seek support are not weaker, but stronger. The ability to confront one's fears and insecurities is a sign of emotional maturity, not a weakness. Philosophically, the concept of virtue ethics highlights the importance of cultivating moral character, and courage is central to this. It's not just about individual achievement, but about contributing to a better world through courageous action.

The wind of change is blowing, urging men to redefine masculinity. It's a call to embrace the full spectrum of human experience, including vulnerability and imperfection. It's a call to cultivate the courage to be authentic, to lead with empathy, and to live a life of purpose. The question remains: what small act of courage will you embrace today? What fear will you confront? What battle will you choose to fight? Begin by taking that first step, however small. The journey of courage is a lifelong pursuit, and each step forward, no matter how hesitant, is a victory.

Try this exercise:

The Alexander Challenge: Embracing Courage This Week

We challenge you to embody the courage of Alexander, not through grand gestures, but through small, deliberate acts of bravery. This isn't about conquering empires, but about conquering your own inner battles.

1. Journaling: Identify one specific fear that's been holding you back. It could be anything – speaking up in a meeting, initiating a conversation, expressing a feeling. Now, write down one small, manageable step you can take this week to confront that fear. This step should be achievable and feel slightly uncomfortable, pushing you just outside your comfort zone.

2. Self-Reflection: Reflect on one area of your life where you could use more courage. Is it in your relationships, your career, or a personal project? What's preventing you from acting with more courage in this area? Write down your thoughts and identify a potential obstacle to overcome.

3. The Courageous Act: This week, commit to performing the small step you identified in your journal entry. This might involve a brief conversation, a small task that makes you feel slightly uneasy, or simply expressing a thought or feeling you've been holding back.

4. Vulnerability Conversation: Share your experience (or a part of it) with a trusted friend, family member, or mentor. Talking about your vulnerability can be incredibly powerful, and sharing your journey with someone else can help solidify your courage.

Remember, courage isn't the absence of fear, but acting despite it. This week, focus on progress, not perfection. Even the smallest step forward is a victory. Celebrate your accomplishments, no matter how small they may seem. The journey of courage is a lifelong pursuit, and each step you take this week will strengthen your resolve for the weeks and years to come.