From the bestselling author of Team of Teams and My Share of the Task, reflections on character, and who we choose to be.
“Reputation is what men and women think of us; character is what God and angels know of us.”
—Thomas Paine
How to measure a life? After a career of service, retired four-star general Stanley McChrystal had much to contemplate. He pondered his successes and failures, his beliefs and aspirations, and asked himself, Who am I, really? And more importantly, who have I become? When I die, how will I be measured?
In the end, McChrystal came to a conclusion as simple as it was the reality of who we are cannot be recorded in dates or accomplishments. It is found in our character—the most accurate, and last full measure, of who we choose to be.
On Character offers McChrystal’s blueprint for living with purpose and integrity, challenging us to examine not just our deeds but who we become through them. Drawing from a lifetime of experience, he distills profound insights on setting and meeting standards, aligning actions with beliefs, and offers practical advice on overcoming obstacles and pursuing self-improvement.
According to McChrystal, character is not a trait inherited at birth, nor does it automatically come from education, position, or experience. Character, instead, comes down to a succession of choices, most mundane, several momentous, that reveal the deep truth of our capacity for virtue.
In an era where understanding and upholding our ideals is more crucial than ever, On Character offers an inspiring roadmap for personal growth and integrity—a call to become our best selves, both as individuals and as Americans.
Stanley Allen McChrystal (born August 14, 1954) is a retired United States Army General. His last assignment was as Commander, International Security Assistance Force (ISAF) and Commander, U.S. Forces Afghanistan (USFOR-A). He previously served as Director, Joint Staff from August 2008 to June 2009 and as Commander, Joint Special Operations Command from 2003 to 2008, where he was credited with the death of Abu Musab al-Zarqawi, leader of Al-Qaeda in Iraq, but also criticized for his alleged role in the cover-up of the Pat Tillman friendly fire incident. McChrystal was reportedly known for saying and thinking what other military leaders were afraid to; this was one of the reasons cited for his appointment to lead all forces in Afghanistan. He held the post from June 15, 2009, to June 23, 2010.
Following unflattering remarks about Vice President Joe Biden and other administration officials attributed to McChrystal and his aides in a Rolling Stone article, McChrystal was recalled to Washington, D.C., where President Barack Obama accepted his resignation as commander in Afghanistan. His command of the International Security Assistance Force in Afghanistan was immediately assumed by the deputy commander, British General Sir Nicholas "Nick" Parker, pending the confirmation of a replacement. Obama named General David Petraeus as McChrystal's replacement; Petraeus was confirmed by the Senate and officially assumed command on June 30. Days after being relieved of his duties in Afghanistan, McChrystal announced his retirement.
In 2010, after leaving the Army, McChrystal joined Yale University as a Jackson Institute for Global Affairs senior fellow. He teaches a course entitled "Leadership," a graduate-level seminar with some spots reserved for undergraduates. The course received 250 applications for 20 spots in 2011 and is being taught for a third time in 2013.
McChrystal co-founded and is a partner at the McChrystal Group LLC, an Alexandria, Virginia-based consulting firm.
McChrystal's memoir, My Share of the Task, published by Portfolio of the Penguin Group, was released on January 7, 2013. The autobiography had been scheduled to be released in November 2012, but was delayed due to security clearance approvals required from the Department of Defense.
McChrystal is the son of Mary Gardner Bright and Major General Herbert J. McChrystal, Jr., and was the fourth child in a family of five boys and a girl, all of whom would serve in the military or marry military spouses. His older brother, Colonel Scott McChrystal, is a retired Army chaplain, and is the endorsing agent for the Assemblies of God.
McChrystal married his wife Annie in April 1977, and the couple has one adult son, Sam.
I love this book, and I think every American should read it. General McChrystal encourages readers to think critically about who they are, what they value, and why. His focus isn’t to get you to see the world the way he does. Instead, he provides perspective and encourages reflection. Give yourself the gift of picking up and reading this book. You’ll be better for it.
The fifth book of McChrystal’s that I’ve read, I remain impressed by his integrity and (no pun intended) character. This wasn’t his best book. There isn’t a clear narrative arc to it; they’re vignettes on various topics loosely based on character, morality, and the important choices in life. Some are humorous. Some are serious. Many are loving.
The chapter I anticipated most was his thoughts on the U.S.’s exit from Afghanistan and the nearly immediate return of the Taliban to power. I think he chose his words almost too carefully, or perhaps it was edited or redacted to obscurity. Either way, it felt like he minced his words too finely.
Nonetheless, I have tremendous respect for General McChrystal. The world needs more leaders and thinkers like him.
It is interesting to read the confusion in reviews by a few readers thus far. I knew from the beginning what Gen. McChrystal was aiming to achieve: This is his last will and testament of a life well served. It is his parting gift of lessons as if we were his grandchildren. For that, it achieves his purpose and I am grateful for his gift. Thank you, Gen. McChrystal.
Confusing. Not sure what the book is actually about. His thoughts are all over the place. The only thing I immediately realized is that this general truly likes himself. His ego is large.
I never probably would’ve picked this book and I didn’t like this book but it was for a work book club so I can’t tell them I didn’t like this book, but you all should know I didn’t like this book
This is a masterpiece. A clarion call to depth of character and graphic depiction of what that is and isn’t. I wish for our nation everyone would get a chance to read it and be transformed by it.
4.5 stars rounded up. I’m cautiously optimistic about McChrystal books, as they’ve started to recycle content a bit too much for my taste, blending together in a Huel-like sludge that’s technically palatable but eminently mundane.
This book is not that, it’s actually quite good.
Maybe it’s because McChrystal is now into his 70s or he’s less focused on his consulting work, or perhaps I’m the one who’s changed since his last book, but the vibe is solid and reflective. Much more “Meditations” than machismo.
If you’re looking to do some of your own reflection, this book is a useful partner. I’m better for having read it and expect to read it again. Check it out.
Encouraged by its appearance on various summer reading lists, I thought this was worth a go. And it’s definitely a quick, summer-y read (if you’re in the mood for something introspective).
Where the book is at its best is where McChrystal talks about the role of discipline in building character - even though you get the strong sense that he’s pulling punches (running US special forces in the mid-2000s comes with the sort of disciplinarian mindset that you suspect may have lots of edges sanded off before it is written down). It is less persuasive in that it tries to be too accommodating of lots of different interpretations - which works as the author is now fifteen years retired, but which still doesn’t ring entirely true.
Despite being a short book, this felt like one of the 30-mile marches the general is so fond of referring to. I’d recommend David Brooks for more serious contemporary writing on character. Sincerity, while admirable - and this book is full of it - is not a substitute for argument.
There’s no new moral framework, exploration of psychology or even much philosophy. There’s certainly nothing that reaches the level of a thesis. While the Stoics make cameos, they don’t elucidate any novel arguments.
“I’ve done my duty, you should consider doing yours” is perhaps the most coherent message.
This is followed closely by the observations that we are imperfect and that in time we will be forgotten.
And so perhaps, in these reflections on our flawed and fleeting nature, this book embodies - however unintentionally - its very message.
In the vein of Marcus Aurelius, McChrystal reflects on events that shaped his values and beliefs. While no Meditations, the reflections are easy to read over breakfast to start the day.
This was really good. I say that as someone fairly well read in the realm of biographies and even more well read in biographies of military leaders in particular. McChrystal did a good job. He also has done a GREAT job moving past the issues around the end of his time in the military in a healthy and productive way which is fantastic to hear. There wasn't a hint of bitterness I was able to detect and that in fact says a lot about his personal character.
In On Character: Choices That Define a Life, General Stanley McChrystal shares stories and lessons from his time as a soldier, leader, and coach. The book feels like reading his personal journal, filled with moments of honesty and reflection. He looks back on what shaped his values and how they guided his choices. McChrystal says real character comes from the mix of conviction and discipline—the beliefs we hold and the effort we make to live by them.
He doesn’t focus on battles or war stories. Instead, he talks about what it means to live with purpose, raise a family, stay loyal to friends, and prepare for loss. Each short chapter gives readers a chance to stop and think about their own beliefs and choices. McChrystal admits he’s still learning, still improving, and still trying to live up to his own standards. He invites readers to do the same and to think deeply about what they believe and who they want to be.
Top Takeaways - The book is a personal reflection on the meaning of character and values. - McChrystal defines character as the product of conviction and discipline. - Conviction means knowing what you believe and why it matters. - Discipline means living those beliefs every day, even when it’s hard. - Character shapes what we accept and what we refuse to tolerate. - McChrystal shares lessons from his life as a soldier, leader, and mentor. - He focuses on universal themes like family, friendship, loss, and purpose. - The stories are short, honest, and written in a reflective first-person style. - He reminds readers that character is built over time through choices. - The book challenges readers to think about what they believe and who they want to be.
I just finished reading Stan McChrystal’s new book #oncharacter.
What an extraordinarily thought provoking and deeply inspiring book it is. And timely.
I was struck by many aspects of the book but in particular his provocation to make sure we think for ourselves. That we form opinions after careful consideration and independent analysis.
As you refine your reading list for this summer. I highly recommend adding this
I was gifted this book through a leadership course and had high hopes. Overall I found it underwhelming. The central message—that character is the foundation of leadership and must be cultivated through discipline and values—is important, but it isn’t especially new. Much of the book feels like a rehash of familiar leadership themes I’ve read in countless other works. While McChrystal’s military background gives him credibility, the anecdotes sometimes read more like Reader's Digest leadership vignettes than deep insights, and I often felt the stories ended abruptly, lacking cohesion with the section of the book.
I appreciate McChrystal’s sincerity and agree with his call for integrity in both personal and public life. However, I wish the book had gone deeper into fresh examples or provided more actionable frameworks. As it stands, it’s fine if you’re new to leadership reading, but not essential if you’ve explored the topic before.
Although this is only the second review of his books that I've shared on goodreads, I've actually read four of General Stanley McChrystal's works. His "Team of Teams" is a favorite of mine. And I really enjoyed "Leaders" - although I thought his "Risk: A User's Guide" dragged a little at times.
This latest (and final, according to his Acknowledgments) work falls somewhere in between these other books. I don't think it was quite as good as "Team of Teams." But it definitely is my second favorite of his works.
It's certainly his most personal. To help you understand why, I'll share the jacket description:
"How do we measure a life?
After a distinguished career, retired four-star general Stanley McChrystal faced this question head-on. He reflected on his successes and failures, wrestling with the essential question: Who am I, really? And more important: how will I be measured when I'm gone?
In the end, McChrystal's conclusion was both simple and profound: our true measure isn't found in dates or awards; it lies in our character—the ultimate testament of who we choose to be.
'On Character' draws from McChrystal’s rich experience to explore the discipline required to live up to our beliefs. Through gripping tales of triumph and defeat, he distills powerful insights that challenge us to examine not just our accomplishments but who we become through them.
According to McChrystal, character isn't something inherited or bestowed by education or status. Instead, it emerges from a series of choices - some mundane, others monumental - that reveal our capacity for virtue. It's about living up to our beliefs as individuals, citizens, and fellow Americans, grounded in our convictions and the discipline we summon to uphold them. McChrystal challenges us to reflect on how we can embody our principles in every aspect of our lives, shaping not only our own character but also the fabric of our society."
As you can see from this description, it's a highly reflective work that forces the reader to examine their own character and overall life. To keep score, if you will, of how closely we actually live a life of conviction, discipline, and character as compared to how we could. As he notes near the end of the work:
“In the end, living is the point. Yet it is not when or where we live, but how we live. The score reflects a game’s outcome, but the manner of play defines its quality. The character we reflect summarizes our lives as no other metric can. Until the end, I will judge that my greatest challenge lies in closing the gap between the character I display and what I was capable of. We often hope players will ‘leave it all on the field,’ and our pursuit of character should do nothing less.” [p. 282]
Not exactly a beach read, right?
Still, I highly recommend everyone not only read this deeply personal work, but that they take the time to self-reflect on McChrystal's points. I know I did.
I'll end this review with a few more gems from the book. Even if you don't read the entire work, I think you'll enjoy these powerful excerpts:
“Few concepts are as powerful or as fraught with danger as the idea of They. When we generalize, hyperbolize, and leverage the emotional commitment we’ve created with such binaries, we carry huge responsibilities for what we’ve sown. It may be that life is an inevitable game of us versus them, but we have some control over who we cast for each side.” [p. 24]
“Politics in America are broken. Whether you are conservative, liberal, or something in-between, the current construct doesn’t work. If your car or plumbing don’t function correctly, you fix them. It’s time to fix our politics.” [p. 88]
“Books help us consider stories, including our own life story, as more than a single page we’re on at that moment. We live with the consequences of our actions in the chapters ahead.” [p. 102]
“…great athletes – and most successful people in any endeavor – understand how few things in life are obtained without effort commensurate with their values. Observers might…say, ‘I could never do that.’ Of course they could. They just have chosen not to.” [p. 113]
“I am convinced that few truly great achievements are reached by individuals with an impressive work-life balance, and the price of greatness is, in a word, great.” [p. 120]
“Reputation is what men and women think of us; character is what God and angels know of us.” – Thomas Paine [p. 167]
“…the siren’s call of self-interest is seductive and finds no shortage of willing suitors.” [p. 210]
“I don’t try to be all I once was but also don’t accept being less than I can be.” [p. 265]
“But do think about death. Often. More specifically, about my life thus far and what I can and should do between now and the moment I pass. I hope I’ve been a good man, but I know I haven’t been the person I could have been. And for my remaining time, I’d like to do better.” [p. 277]
A book for all reasons from a man for all seasons.
General McChrystal starts his book with his dedication: “With admiration to all those who live a life of character. And with encouragement to all of us who fall short but continue to try.” Immediately following is René Descartes’s famous quote: “I think, therefore I am.” It turns out I went to the same high school (and the same college) as the General. I believe that when I was there, and correct or not, one of the Christian Brothers mentioned that the “Cogito, ergo sum” expression could also be read, “As I think, therefore I am.” It is on this basis, and whether or not McChrystal meant it this way or not, that I very much enjoyed his book. In support of my theory, I note that not only was McChrystal’s working title for his book “What I Think About the Things I Think About,” but the photograph on the back cover of the book shows him deep in thought.
I would define character simply as steadfast adherence to a strict moral or ethical code. McChrystal defines character as a choice. “It is built upon convictions, or deeply held beliefs, that we embrace and the discipline we muster to live up to them.” He also believes that “despite its deeply human nature, it is curiously mathematical: Character [the resulting product] = Convictions x Discipline.” Conviction he defines as “what we believe, and how we enforce those beliefs, form the foundation of our character.” Discipline he defines as “our ability to follow through on our stated beliefs provides the sinew to connect our convictions to the character they are meant to uphold.” In this sense, he defines character as “The essential structure of our lives is what we are willing to tolerate—and what we are not.” With this in mind, McChrystal develops 22 chapters based on Convictions, 18 on Discipline, and the final 28 on Character, with two more added for Epilogue and Acknowledgments. Two of my favorite chapters are back-to-back: the last chapter in Convictions and the first one on Discipline: “Fixing Politics: What you don’t fix will kill you,” and “A Call to Think: The most critical discipline is to think for ourselves.”
In most chapters, McChrystal begins by describing a situation, usually military, from his life. He then reflects upon the general concepts and issues involved. Finally, he returns to the situation and offers pithy, quotable advice based upon the concepts developed and illustrated. Understandably, he gives several examples where he weaves in what he learned at West Point: viz, The Cadet Honor Code: “A cadet will not lie, cheat, steal, or … [tolerate those who do].” And a portion of the Cadet Prayer: “…Make us choose the harder right than the easier wrong, and never to be content with a half truth when the whole can be won.”
Remarkable is that throughout the book, the author strongly recommends persistence in attempting to do good, even though failure occasionally happens to all of us, and admits to it himself in sometimes humorous situations. Humility is a character trait he wears very well.
All in all, and “thinking” about it, I found McChrystal’s book to be a fascinating discourse on his book’s weighty title: “On Character: Choices That Define a Life.” Highly and enthusiastically recommended!
“Heroism, in my view, is not merely a spasmodic response to a single situation,” says the former US Army four-star General. “It is the result of measured actions over time that curatively constitute a level of behavior that sets a person apart from, and above, what we usually suspect.”
McChrystal meets his own high standard.
He is the author of a new book titled “On Character: Choices That Define a Life,” which started simply enough as a series of 800-1,000 word essays McCrystal had written over a period of time. The book’s working title was initially “What I Think About the Things I Think About,” and his agent, editor, and publisher didn’t think much of that title.
More importantly, though, they saw that a single theme was woven through virtually all the passages — and that theme was character. They encouraged him to explore that more deeply, and he did. So throughout the book, McCrystal details the components of a tight mathematical equation that he formulated: Character = Convictions x Discipline.
Each chapter essentially asks the reader a question each of us must ponder and answer for ourselves. This book illustrates McChrystal’s answers, and here are a few of my favorite gems from the book:
“It is found in our character — the most accurate, and last full measure, of who we choose to be.”
“Life, I’ve learned, is mostly about who we decide to be. There are variables we don’t control, such as physical traits we inherit and many of the circumstances surrounding us. But what and whom we choose to believe in, and how those beliefs shape our character, is up to us.”
“At this stage in my life, I am thankful for having as few regrets as I do. But the number isn’t zero. I certainly regret the instances when I felt the organization let me down, but I can live with those. Sometimes, I even indulge in self-pity. But the moments I truly regret are the ones when I believe I could have stood stronger for someone who depended on me or when I let the organization fail a teammate. That really haunts me and drives me to do better next time.”
“I try to remember that rational, well-intentioned people can reach very different conclusions on knotty issues. I admit that my own views reflect life’s journey, and I could just as easily have arrived at very different opinions were my circumstances different.”
“In the end, much of this is a matter of accepting that life is an arc, not an ever-ascending slope we climb to all we ever dreamed. I don’t try to be all I once was but also don’t accept being less than I can be. Do I miss seeing them and waiting when the plane lands? Not really. But do I miss being someone people want and need in the room? Sometimes, I do.”
I think it’s important to note that in 2010, General McCrystal was the leader of the allied forces in Afghanistan. However, after a Rolling Stone article was published in which some members of his staff made unflattering remarks about the Commander-in-Chief, President Obama accepted McChrystal’s resignation. The video clip link below comes from the first public interview McChrystal gave after being fired. The pain, disappointment, embarrassment, and a hint of anger are evident.
Please watch it. After you do you’ll understand why I started out by calling Stan McChrystal a hero. Well, he is that and more. He is a man of conviction, discipline, and indeed, character.
I went into this thinking this would be an exploration of McChrystal's interpretation of what is meant by character, how he thinks about it, why he thinks it's important, what he thinks about what others have said about the importance of character, and so on. And, to some extent, the book has bits and pieces of these topics. But he has approached the topic differently than this. On Character is made up of dozens of short chapters (no more than 4-5 pages each) about a topic ranging from McChrystal's thoughts on the uses and limitations of anger, the importance of civil rights, whether the US was successful in Afghanistan, not fixating on our differences, and so on. These chapters are grouped into three larger sections, and the sum of all that is actually supposed to be an illustration of McChrystal's character more than a rumination on character broadly.
That's fine and I don't think it necessarily makes the book better or worse...but it just wasn't what I was expecting or hoping for. I didn't care for the short chapters. I assume this was a purposeful constraint McChrystal imposed on himself in order to cover a wider array of subjects, but I think he did himself and his readers a disservice by doing that. If he wants us to approximate his character from these shorter chapters, then it stands to reason he would want us to have as many data points as possible to get a more accurate estimate. At well over 30 such chapters, whatever conclusion the reader makes should be statistically significant in that case. But I think the gains you get from a larger sample size here have to be balanced against the declining marginal return of having so many chapters that don't delve very deep.
But having only 4-5 pages to cover a topic prohibits much deep exploration or affords any time to trace interesting threads. Many times you're reading a chapter and he writes one sentence that cracks open a potentially deeper discussion...but then it's gone because there's no time. I also get the feeling that he had to cut a ton of extra prose out of many chapters to fit them under the 5 page threshold, and so sentences will share a paragraph, but not necessarily a clear line of thought.
Stanley McChrystal’s “On Character: Choices That Define a Life” is a deeply reflective exploration of what it truly means to live with integrity, drawing on the retired four-star general’s decades of military service and personal introspection. Unlike many leadership books that focus on tactics or charisma, McChrystal argues that **character is the ultimate metric by which a life should be measured**—not rank, reputation, or even happiness, but the sum of our convictions and the discipline to live by them. McChrystal’s central formula—**Character = Convictions × Discipline**—distills a lifetime of experience into a deceptively simple equation. Convictions, he writes, are the “mainsprings of action,” while discipline is the relentless will to act on those beliefs, even when it’s inconvenient or difficult. Without both, character is hollow. He is candid about his own shortcomings, including the public end to his military career and regrets as a father, using these moments not for self-pity but as lessons in humility and growth. The book is structured around three pillars: - **Conviction:** Deeply held, pressure-tested beliefs, not just inherited or assumed values. - **Discipline:** The daily, sometimes mundane effort to act in accordance with those convictions. - **Character:** The cumulative result of choices, big and small, that reveal our true selves. McChrystal’s writing is practical and grounded, often reflecting on how character is forged through adversity and the importance of aligning actions with values—even when no one is watching. He warns against the erosion of character in modern society, urging leaders and citizens alike to close the gap between stated ideals and lived reality. What sets “On Character” apart is its blend of soldierly wisdom and personal vulnerability. McChrystal doesn’t offer easy answers or prescriptive steps; instead, he invites readers into a conversation about what it means to become our best selves, both individually and collectively. In an era of cynicism and division, his call to build character—one choice at a time—feels both urgent and refreshingly timeless.
Reading this book is like saying your nightly prayers, eating one meal only everyday, respecting your country, making your bed neatly in the morning, remembering to write hand written thank you notes, never quitting anything tough, stepping up to leadership roles with empathy and modesty even when commanding thousands of troops in combat missions overseas. If you have done all this and less, you are "On Character: Choices that Define a Life" according to the admonitions of General Stanley McChrystal.
It's a book filled with little three and four page chapters of life lessons. None of them are eye opening or gob smackingly elucidating. They are wise, sage, timeless advice from a man who achieved the highest glory of military service and is now prosperously living his post fighting years through public speaking engagements, book writing, pension collecting and working within Washington to advise and profit monetarily from other government agencies.
The author is 71, and his age and generation marinate the life lessons of this book.
If you have ever experienced a stern, unsmiling grandma who told you to sit up straight and finish everything on your plate, or sat in class while a sadistic teacher chewed you out for not paying attention, and if you enjoyed all these moments, you will surely enjoy this book of somnambulistic stories.
Postscript: I thought more about this book, which is on the surface about values, integrity and morality. It has another layer of subversive and thoughtful critiques of how the US and its people behave, think, justify and delude themselves in politics, war and personal life. The general does this without naming the orange elephant in the room, but clearly, assuredly and deliberately, he tears down Trumpism and its toxins by elucidating the best and worst examples of grace under pressure, often using his own life as a teaching aide. He contrasts honor, integrity and ethics with their antonyms.
To read this book is to partially rediscover what it means to think and act with conscience. And for that reason alone it possesses high value as a type of agnostic good book of wisdom.
My military career overlapped with Gen McChrystal's for twenty of the thirty years I served. He was a respected military leader in the vein of James "Maddog" Mattis, with a reputation for leading from the front. When he "resigned" from the service, it was not a surprise to me that the reason was unrelated to a moral failing, nor even something he personally said, but for actions that happened while he was in charge--actions he was responsible for. He acknowledged that responsibility and tendered his resignation.
In his latest book, "On Character," General McChrystal reflects on a life of service to explore what truly defines us—not our accomplishments, but the choices we make and the values we uphold. In clear and simple language, he argues that character is built deliberately over time, shaped by everyday decisions (how you wait for your luggage at the airport) as much as pivotal moments.
The book resonated with me. He doesn't claim every leader has a flawless character--he argues every good leader should strive for their best character. None of us is perfect. Maybe I was drawn by his call for integrity in a social media-driven world, where the concept is sorely lacking. Maybe it was because he talks about what it's like to think about character in the later years of life. The events you should look back on, and how you reflect on them. His book is part memoir, part love story to his wife and family, and a call to live with purpose and principle even after you graduate from leadership roles.
"Character" is my favorite topic, as I'm sure my Cadets, students, Scouts, and children could tell you. In over 50 years of life on this planet, including 27 in the Army, the biggest lesson I've learned is the importance of character. In the Army, character is the first leader attribute (of three--also presence and intellect), and I was fond of telling my Cadets it is first for a reason--because it's the most important. So I thoroughly enjoyed Gen. McChrystal's book on character. Despite stating he hoped the reader would not agree with everything he wrote, I found myself agreeing with him in almost all of his reflections and life lessons. The one area I might diverge is about the importance of religious faith in my life. For me, it is vital. McChrystal states he is a bit undecided about this. Elsewhere, McChrystal discusses the importance of standards (in one chapter) and discipline (throughout the book). These are two elements I've always been keen to reinforce with my Soldiers, Cadets, and even my own children. He does an excellent job of reinforcing why these are so important to overall character. One day--perhaps 19 years from now when I'm the age McChrystal was when he wrote this book, I hope to be able to document my own life lessons and keys to success for my children and grandchildren. If not, I will recommend this book to them as an excellent stand-in.
McChrystal’s On Character is the kind of book that feels less like a lecture and more like a quiet talk with someone who has seen a lot and lived through the weight of his choices. It’s steady, disciplined, and at times almost too polished, but underneath there’s a humility that carries the pages forward.
What I appreciated most was that he doesn’t beat his chest. He isn’t trying to sell you on the myth of the general. Instead, he keeps circling back to the daily decisions that shape who we are when no one is watching. Integrity. Discipline. Humility. These aren’t presented as slogans but as habits carved into a life over time.
The writing can get stiff in places. There are moments when the prose feels like a uniform that’s been pressed too sharp, when a simpler word would have landed harder. But even then, it never loses sincerity. It lingers with the burn of a good bourbon—sharp in the throat, warm in the chest, worth sitting with.
I don’t think this book will fire anyone up in the way a lot of leadership or self-help books try to. It’s quieter than that. Slower. More reflective. The kind of book you read, set down, and find yourself thinking about the next time you’re faced with a choice that doesn’t have an audience.
Four stars because it doesn’t need to be perfect. It just needs to be honest. And this one is.
I find myself going to Stan McChrystal’s books like a moth to a flame. I tend to define my professional life in chapters by which McCrystal book I read most recently. On Character: Choices That Define a Life reminded me how much character shows itself when pressure is highest. In demanding environments, people notice quickly whether actions truly align with stated values, and even small lapses can ripple across a group and affect the culture in a negative way, in such a manner that is not recoverable, and it's a professional death sentence for the person responsible for cohesion. Organizations are sometimes defined by the dark periods of bad leaders, like some would discuss Picasso's Blue Period or residents of Sarajevo talk fondly of the 1992–1996 Siege during the Bosnian War. The small team's leader will quickly paint themselves as ineffective and disingenuous, and that will be their legacy. What struck me in McChrystal’s reflections is how trust and cohesion come not from dramatic speeches or authority, but from consistent choices made in the moment; choosing fairness over expedience, humility over ego, accountability over excuses. I’ve seen how those quiet decisions can steady a team when circumstances are toughest, which made this book feel less like abstract philosophy and more like a confirmation of lived reality.
I bought the book because I was way down on the library wait list. In retrospect, I wish that I'd waited. It's not bad, but it seems like a collection of thoughts for his family (probably for his granddaughters) and posterity. The original title ('What I Think About the Things I Think About' according to the Acknowledgements at the end) gives a more accurate sense of its contents. The publisher has done a good job of renaming it and packaging it for sale, but the result (I fear) is misleading. The 19th century book 'Character' by Samuel Smiles, or the David Brooks book 'The Road to Character' are more useful. Here we find reminders that handwritten notes are good. Maybe try the OMAD ('One Meal A Day') diet for weight control and discipline. 'Character' is actually part 3 of the 3-part book (part 1 being 'Conviction', and part 2 being 'Discipline'). But again, the book felt like a miscellaneous collection of opinions, thoughts, and memories. Reflections on mortality take over at the end, but this is understandable for an elder gentleman. For a retired general he is surprisingly liberal (pro-civil rights, anti-death penalty, pro-abortion, a believer but not apparently religious). YMMV.
The central idea of this book is that convictions combined with discipline form the foundation of character. This concept applies not only to individuals but also to organizations and even nations. Stanley McChrystal reflects on a wide range of topics, including torture, teamwork, U.S. politics, and family.
The main point of the book is interesting and worth reflecting on. However, McChrystal spends relatively little time systematically developing his thesis, and much of the text feels disorganized—almost like a stream of consciousness.
The most valuable takeaway is the emphasis on thinking about our values first and foremost, both at the individual and organizational levels. While this is certainly not a new idea, it remains an important one. It would have been more impactful if explored in a more structured and logical manner. For example: What are a nation’s values? How should they influence foreign and domestic policy? What are our personal values? How should they shape our professional choices and interactions with others? McChrystal touches on these questions, but rarely in depth.
I wouldn’t strongly recommend this book. Some of McChrystal’s interviews might be worth listening to, and the questions he raises are worth pondering—but this book itself does not address them in a satisfying or coherent way.