The Quiet Strength of Courage & Philosophy
Dear Faithful Companion,
As I sit at my desk, the cover of Courage is Calling by Ryan Holiday captures my focus—a powerful reminder of my commitment to make 2025 a year of growth and self-improvement. This is the first of twelve books I’ve chosen to read throughout the year, each selected to inspire and challenge me as I strive to better understand myself, navigate life’s complexities, and lead with purpose and conviction.
Thanks to Adam, stoicism has grown into a cornerstone of my life—not just as a philosophy, but as a practical framework for living well. It’s been incredibly rewarding to see many of my friends develop their own interest in stoicism. Some discovered it before I did, while others I’ve had the privilege of introducing to the subject. Sharing insights and reflecting together on how these timeless principles apply to modern life has deepened my appreciation for this philosophy.
Ryan Holiday has been a pivotal guide on my journey. I follow his Daily Stoic, subscribe to his emails, listen to his podcast, and even had the pleasure of attending one of his live lectures. I’m especially grateful to Rob for inviting me to see Ryan Holiday in Toronto last December. What started as a simple invitation turned into a memorable boys’ night out with Rob and Ray—filled with great conversation, laughter, and mutual admiration for a writer whose work continues to inspire us all.
In Courage is Calling, Holiday explores the nature of fear and courage in ways that are both timeless and deeply relevant. One passage that stood out comes from the chapter “Fear Is a Self-Fulfilling Prophecy”:
“Fear leads to poor decisions. Fear makes us follow the herd. Fear makes us hesitate. Fear leads to overreaction. Fear creates destructive patterns and habits. Fear is the enemy.” (Courage is Calling, p. 43)
This observation is as true in personal life as it is in leadership. Fear, at its core, is a powerful force—one that often drives hesitation, overthinking, or reactive decisions that fail to align with our values or long-term goals. It clouds judgment, fosters doubt, and, if left unchecked, can paralyze us into inaction. Yet, stoicism offers a transformative perspective: fear is not an insurmountable roadblock but rather a signal, an invitation to step forward and act with intention.
Courage, in this context, is not an extraordinary or rare virtue reserved for those grand, life-altering moments we envision in stories. Instead, it is something far more accessible, something we can all cultivate. Courage is like a muscle, strengthened through small, deliberate actions that compound over time. It shows up in everyday life—in the willingness to confront an uncomfortable truth, to make a decision without perfect certainty, or to persevere through a difficult task despite self-doubt. Each act of courage, no matter how seemingly insignificant, builds a foundation of resilience, empowering us to face larger challenges with greater resolve.
By viewing fear as an opportunity rather than an obstacle, stoicism helps reframe how we approach life’s uncertainties. It teaches us that courage is not about the absence of fear, but about moving forward despite it. This shift in mindset not only enables personal growth but also sets an example for others to follow, whether in our roles as leaders, friends, or family members.
Inspiration is only as valuable as the effort we put behind it. Picasso’s words, “Inspiration exists, but it has to find you working,” serve as a powerful reminder that action transforms inspiration into progress. Stoicism is rooted in this very principle: it’s not enough to admire courage, wisdom, or discipline; one must actively practice these virtues in daily life.
For me, that means taking the insights I gain from Holiday’s work and turning them into deliberate, meaningful actions. Whether it’s making decisions with clarity under pressure, articulating lessons to my team, or showing up consistently even when challenges seem daunting, the philosophy of stoicism provides a framework for channeling inspiration into action.
This is a philosophy anyone can apply, regardless of their circumstances. Courage might mean starting something you’ve long put off, taking responsibility for your actions, or simply committing to daily habits that align with your values. It’s in these seemingly small but intentional acts that we shape the course of our lives and find strength in moments where fear might otherwise prevail.
Verbum Ultimum: The quiet strength of stoicism reminds me that courage is not extraordinary but habitual—a way of meeting life head-on with determination, clarity, and purpose. I’m thankful for the inspiration I’ve found in this book, the conversations I’ve shared with friends, and the reminder that we’re all capable of turning our inspiration into meaningful action. Let inspiration find us working, so that courage may shape the days to come and wisdom may guide the journey forward.
Until next we meet, with ink as my witness and virtue as my guide.
JCB
