I did not set out to use artificial intelligence as part of my writing process. Like most things in my work, it began as a practical response to a problem. I was trying to clarify an idea—tighten an argument that felt structurally sound but poorly expressed. The tool I was using responded with something unexpected: not just a rephrasing, but a reframing. It wasn’t always correct. Often it wasn’t. But it forced a different question: ...
Stoic Backgammon A Profitable Pastime Executive Summary Stoic Backgammon treats the ancient game as a practice of philosophy—not metaphorically, but literally. Each chapter pairs a phase of play with a Stoic principle, demonstrating that the board enforces what the Enchiridion describes: some things are up to us, others are not. The dice are not; the move is. The core message: the right response to uncertainty is not prediction but character. ...
Letters Truth Without Outcome Executive Summary Letters collects correspondence on the difficult topics that most public discourse avoids: what it means to speak the truth when outcomes are uncertain, how conscience functions under pressure, and whether interior strength has any public value. The essays are written as letters—direct, addressed, unguarded—because the subject matter demands intimacy rather than performance. The core message: honest speech is not a strategy for winning. It is a practice of remaining present. ...
Misaligned Right Subject, Wrong Adjective, Disastrous Result Executive Summary Misaligned begins with a late-life diagnosis and follows its implications outward: through a first marriage that ended in miscommunication rather than malice, through a career built on containment, and through the slow recognition that many strengths become liabilities when the context changes. It treats the gap between internal experience and external expectation as a structural problem, not a personal failure. The core message: alignment is not a state to achieve—it is a map to question. ...
The Stoic CGM A Data-Driven Guide to Reinventing Yourself Executive Summary The Stoic CGM treats continuous glucose monitoring as a practice of self-knowledge—not merely a medical intervention, but a discipline of attention applied to the body’s own politics. It examines what happens when Stoic principles meet metabolic data: how to respond to information without being ruled by it, and how to govern the self when the self is constantly in motion. The core message: the body is not an enemy to defeat, but a system to comprehend. ...
🪞 A Reflection “Nearly all men can stand adversity, but if you want to test a man’s character, give him power.” — Abraham Lincoln Power has always been the ultimate mirror. It reflects what we are when nobody can stop us. Titles and elections make it look formal, but the real test happens in smaller, quieter places—at a desk, in a meeting, in how we handle the people who can’t fight back. That’s where character either deepens or curdles. ...
Look again at that pale blue dot. A speck suspended in sunlight. Every person you’ve ever loved. Every shout, every triumph, every quiet act of grace. All of it, balanced on a pixel. Distance compresses us. It turns conflict into noise and perspective into truth. From out there, certainty looks small. Humility looks like intelligence. Curiosity looks like courage. The Pale Blue Dot does not diminish us. It clarifies us. ...
A Life Made Whole Essays on Inner Strength and Resilience Executive Summary A Life Made Whole examines the long process of integration—not the dramatic breakthroughs, but the daily work of holding together what experience threatens to fragment. It treats the Stoic virtues not as ideals to achieve, but as practices to maintain under pressure, loss, and the slow erosion of circumstance. The core message: wholeness is not a state to reach, but a direction to hold. ...
🪞 A Reflection When people talk about investing, they usually focus on charts, PE ratios, or the “hot” asset of the moment. But Morgan Housel, in The Psychology of Money, reminds us that the hardest part of investing isn’t math — it’s behavior. Your emotions, your patience, and your discipline will determine more about your wealth than any spreadsheet ever will. Wealth Is What You Don’t See Wealth isn’t the car in the driveway or the vacation photos online. Real wealth is invisible: the money you quietly didn’t spend, the patience you showed when others splurged. For retirees, that discipline decades ago is what pays dividends today. ...
Markets are very good at finding the weak joint in a man’s composure. You can believe yourself disciplined when the line is moving up and to the right. You can quote long-term return data, admire compound interest, and say the proper things about patience. Then the market drops hard before lunch, the headlines turn red, and the abstract virtue becomes a practical test. The question is no longer whether you believe in discipline. The question is whether discipline still has your hands when fear reaches for the keyboard. ...