SourceFebruary 24, 2026clippings

Philosopher's Notes | On Character

On Character

Choices That Define a Life

About the Book

Brian's take

I read this book the day after I read Admiral William H. McRaven’s Conquering Crisis. Admiral McRaven and General Stanley McChrystal are two of my favorite leaders and authors, and they both share the same rare combination of real world gravitas and practical wisdom you can apply immediately. This is the second Note I’ve created on one of General McChrystal’s books, and On Character is exactly what the subtitle promises, a collection of sharp, thoughtful essays on the choices that define a life, organized into three parts: Conviction, Discipline, and Character. McChrystal gives us a simple equation that is as elegant as it is demanding, Character = Convictions x Discipline, meaning if you lack either deeply held beliefs or the discipline to live up to them, the product is zero. Big Ideas we explore include character as convictions multiplied by discipline, your life take two, obsession as the price of the exceptional, what a hero really is, and closing the gap with the final roll call.

“Convictions are the mainsprings of action, the driving force of life.”

What a man lives are his convictions.

Bishop Francis Kelley, former military chaplain

“Reputation is what men and women think of us.”

Character is what God and angels know of us.

Thomas Paine

“Getting your priorities right should be priority number one.”

General Stanley McChrystal

“The common denominator in most great leadership isn’t superior recruiting, clever game plans, or motivational slogans.”

It’s about setting high standards and embodying them. It’s not complicated or sophisticated, just difficult. And sometimes, that’s the secret.

General Stanley McChrystal

“Our circumstances are often not of our making, but what we do with them is.”

Some endings are not really the end; they’re just an opportunity to keep moving forward.

General Stanley McChrystal

“When all is said and done, knowing who we are is more difficult than it seems. I have a model for the person I want to be and often am, but all too frequently reality intervenes and I see myself falling short in ways that disappoint and sometimes surprise me.”

In those moments, I find that I must simultaneously demand the most from myself and allow for failure. Life, I’ve found, is a never-ending effort to embody values we admire.

General Stanley McChrystal

“And we can deceive ourselves—in which case I have rationalized my way to amorality, and that’s not something I’m willing to do.”

To be sure, lax convictions can be liberating for those who hold them but I judge such unwillingness to commit as pathetic. At the very least, these individuals may console themselves that they are not alone.

General Stanley McChrystal

“The West Point Cadet Prayer captures the essence of behaving as we should, regardless of the costs: ‘Make us to choose the harder right instead of the easier wrong, and never to be content with a half truth when the whole can be won.’”

General Stanley McChrystal

“But as our politics drift ever closer to demagoguery and digitally enabled mob rule, I watch self-proclaimed leaders of character debase themselves in the mistaken hope that political success includes redemption.”

It will not.

General Stanley McChrystal

“As Marcus Aurelius reminds us, to act with the hope or expectation of being remembered or honored by future generations is pointless.”

Those generations pass away, too. Instead, he advocates not complicating our calculus. Just do what we believe is right simply because it’s right.

General Stanley McChrystal


Character = Convictions x Discipline

28:21

Introduction

From the book

“If I’m ultimately buried at Arlington National Cemetery, my grave, by regulation—and just like my father’s—will be marked with a 13” x 42” x 4” white marble headstone upon which a maximum of eleven lines of text will record my name, dates of birth and death, military service, final rank, and perhaps the wars in which I served.

On the other side will be my wife’s name and the dates of her life. Those lines are not much to record the essence of who we were, but they aren’t intended to. That reality, more difficult to define, cannot be recorded in dates, accomplishments, or even perceived successes and failures. It is found in our character—the most accurate, and last full measure, of who we choose to be. Every other metric is superfluous. So, this is a book abut character, but one necessarily constructed of my convictions.”

Brian's Notes

I read this book the day after I read Admiral William H McRaven’s book, Conquering Crisis.

Admiral McRaven and General McChrystal are two of my favorite leaders and authors.

I’ve created Notes on all five of McRaven’s books, including Make Your Bed (which he published after his commencement address went viral), Sea Stories (his autobiography), The Hero Code, The Wisdom of the Bullfrog, and Conquering Crisis.

This is the second Note I’ve done on one of General McChrystal’s books. Check out my Notes on Leaders: Myth and Reality.

As per the back flap of the book: “After thirty-four years of service in the US Army, Stanley McChrystal retired as a four-star general. He was commander of the International Security Assistant Forces in Afghanistan and previously served as commander of the nation’s premier counterterrorism force, the Joint Special Operations Command.”

He’s the author of My Share of the Task, Team of Teams, Leaders, and Risk. He’s also the founder and CEO of McChrystal group, a leadership consulting firm.

This book is, as per the sub-title, all about the choices that define a life and, of course, how to make those choices wisely. (Get a copy here.)

McChrystal says he was originally going to call it What I Think About the Things I Think About —which would have been the perfect title, albeit a little less laconic than what we he went with. The book features dozens of brief essays and is organized in three parts: Conviction, Discipline, and Character.

As you’d expect, it’s packed with Big Ideas. As always, I’m excited to share a few of my favorites and help you apply them to your life TODAY so let’s jump straight in.

P.S. Check out my Notes on books by other Generals: Colin Powell’s It Worked for Me and Jim Mattis’s Call Sign Chaos.

And, check out my Notes on books by other Admirals including: James Stockdale’s Courage Under Fire and Thoughts of a Philosophical Fighter Pilot, James Stravridis’s To Risk It All, Bob Harward’s The Gouge, and Mike Manazir’s Learn How to Lead to Win.


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