I. Overview and Central Argument: On Character

General Stanley McChrystal’s book, “On Character,” serves as a late-in-life introspection and exploration of what constitutes character and how it is developed. The central argument, explicitly stated, is that “IN THE END, CHARACTER IS THE ONLY METRIC THAT MATTERS.” McChrystal defines character with a simple, yet “thunderously consequential,” equation: Character = Convictions × Discipline. He posits that a lack of either substantive convictions (what you believe) or discipline (the will to act on those beliefs) renders character valueless. The book is a personal search for this character, acknowledging that his own “neither… nor character are all that they could be, or even all that I wish they were,” but emphasizes that it is a continuous “work in progress.”

II. Key Themes and Ideas:

The excerpts highlight several interconnected themes crucial to understanding McChrystal’s perspective on character:

• The Primacy of Character: Character is presented as the ultimate measure of a person’s worth, transcending external metrics like military rank, wealth, public acclaim, or even happiness. It is “what God and angels know of us,” in contrast to reputation, which is “what men and women think of us.”
• Character as a Product of Convictions and Discipline: This foundational equation is central. Convictions are described as the “mainsprings of action,” the “driving powers of life.” Discipline is the “will of an individual to consistently do what they believe is right,” requiring constant effort and practice.
• The Importance of Deep Reflection and Circumpection: Reaching substantive convictions “demands deep reflection.” McChrystal argues against a narrow introspection focused solely on one’s own life, advocating instead for “circumspection” – looking around and considering all angles to understand the world and oneself more holistically. His own sudden career ending was a catalyst for this deep thinking.
• The Influence of Experience and Environment on Convictions: While advocating for individual thought, McChrystal acknowledges that beliefs and perspectives are significantly shaped by one’s environment and journey. He uses the example of the Pashtun elders and even al-Qaeda suicide bombers to illustrate how different upbringings can lead to vastly different convictions.
• The Role of Discipline in Living Out Convictions: Discipline is not an inherent trait but a learned skill developed through experience and intentional effort. Mundane acts of self-control, like making one’s bed or adhering to a meal plan, build the habit of discipline which is then applied to more substantive convictions like honesty and how one interacts with others. Falling short of standards “causes me real distress,” reinforcing the value of discipline.
• The Challenge of Living Up to Values: Professing values is easier than consistently living by them. McChrystal uses military examples like the Code of Conduct under interrogation and the “Ship, Shipmate, Self” value to illustrate the difficulty of upholding standards under pressure, both external and internal. He questions whether actions are driven by genuine values or a desire for external approval.
• The Nature of Commitment and the Cost of Quitting: Life presents countless opportunities to commit, and breaking these commitments, even seemingly minor ones, can become a habit that diminishes the value placed on all promises. The decision to quit should be thoughtful, as there are “always consequences that someone has to pay.” The Ranger School experience highlights the struggle between the desire to excel and the difficulty of enduring hardship.
• Trust as Sacred and Systems for Ensuring Trustworthiness: Trust is presented as a “sacred” element in relationships, although it is not to be taken for granted, especially in the broader societal context where norms and systems enabling trust have eroded. McChrystal values being trustworthy and trying to be honest in every interaction.
• Navigating Moral Complexity and Avoiding Rationalization: Moral standards are not always simple or straightforward. McChrystal discusses the difficulty of setting absolute standards and the temptation to rationalize exceptions based on desired outcomes or advantages. He views a willingness to commit to standards, even when imperfectly adhered to, as essential, judging “lax convictions” as “pathetic.” The Juul Labs example illustrates how even admirable individuals can rationalize actions based on perceived benefits.
• The Impact of Leaders and the Importance of Setting Tone: Leaders are responsible for setting the tone for their teams. The anecdote of the General and his aide illustrates the subtle ways in which leaders’ behavior and expectations influence those around them. McChrystal advises aspiring leaders to “Command like it’s your last job” and be the person and leader the organization needs, rather than making overly cautious decisions to advance.
• Reflecting on the Arc of Life and the End: Considering one’s own mortality and the finite nature of life brings appreciation for what matters most. McChrystal finds value in reflecting on his life’s course, the convictions that have defined him, and the enduring impact of character. He suggests that the true measure of a person may lie in the positive “usefulness” and contribution they make in both trivial and significant situations.
• The Legacy of Character: Ultimately, the lasting impact of a person lies in their character. Family traditions, admired historical figures, and even military monuments serve as benchmarks of values and a “common narrative around which we can coalesce.” McChrystal hopes his granddaughters will judge him by his character rather than traditional accomplishments.

III. Important Ideas and Facts (with Quotes):

• Definition of Character: “Character = Convictions × Discipline” – This is the core formula.
• The Ultimate Metric: “IN THE END, CHARACTER IS THE ONLY METRIC THAT MATTERS.”
• Convictions as Motivation: “CONVICTIONS ARE THE MAINSPRINGS OF ACTION, THE DRIVING POWERS OF LIFE. WHAT A MAN LIVES ARE HIS CONVICTIONS.”
• Discipline as the Means: Self-discipline is defined as “the will of an individual to consistently do what they believe is right.”
• The Continuous Nature of Character Development: His convictions and character “remain a work in progress that can still improve.”
• The Value of Circumpection: McChrystal’s approach to reflection became “to look around, to consider all angles, to seek to understand something more holistically, like beholding a diamond.”
• The Impact of Perspective: “Any object viewed from a single perspective is two-dimensional.” Our environment and journey significantly shape our views.
• The Difficulty of Living Values in Practice: Using the “Ship, Shipmate, Self” example, he notes the “danger of using strong words that may exceed a person’s willingness to live up to them.”
• Questioning Our Motivations: “Even when I act in a manner respected by others, do I do so because of my values or am I searching for approval?”
• The Cost of Breaking Commitments: “But the decision to quit should come thoughtfully, because breaking your commitments becomes a habit. Commitments easily abandoned often reset the value placed on all promises in our lives.”
• The Temptation of Rationalization: “All of us have experienced situations in which an individual’s values are rationalized away in deference to money or some other advantage.” He hopes that he won’t rationalize when it’s tempting.
• Leaders Setting the Tone: “LEADERS ARE RESPONSIBLE TO SET THE TONE FOR THEIR TEAMS.”
• The Importance of Authentic Leadership: “Command like it’s your last job.” Be the leader the organization needs, not one seeking to ascend.
• Accepting the Arc of Life: Life is an “arc, not an ever-ascending slope we climb to all we ever dreamed.”
• The Legacy of Character: McChrystal believes his mother judged him by his character, not traditional accomplishments, and “To this day, it is how I judge myself. When I really think about it, not much else matters.”
• Thinking About the End: Considering death can be a motivator for self-improvement: “for my remaining time, I’d like to do better.”
• The Gift of Conviction: “Instead, I believe I’ll think about the gift of conviction. A life with fewer things to believe in, less opportunity to commit, and little to trust everything to would have been an empty room in which to live.”
• Historical Figures as Inspiration: Monuments and stories about figures like Lincoln and those who chose the “harder right instead of the easier wrong” serve as benchmarks for the values we hope to emulate.

IV. Conclusion:

“On Character” is a deeply personal and reflective work that distills a lifetime of experience, particularly in military leadership, into a compelling argument for the paramount importance of character. General McChrystal emphasizes that character is not a passive trait but an active construction built upon carefully considered convictions and the unwavering discipline to live by them. The book serves as both an examination of his own journey and an invitation to the reader to engage in their own process of self-discovery and intentional character development. The core message is a call to live a life of substance and integrity, acknowledging the constant challenges and temptations that make this endeavor both difficult and profoundly rewarding.

Contact Factoring Specialist, Chris Lehnes

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Study Guide: Exploring Character, Conviction, and Discipline

Quiz

1. According to General McChrystal’s formula, what are the two essential components of character?
2. What does the author suggest is the primary way people are assessed throughout most of life, despite the difficulty of knowing thoughts and convictions?
3. How does the author define “self-discipline” in the context of the text?
4. What phrase is used in the text to describe the choice to embrace difficult or painful situations?
5. What does the author credit as the potential “secret to his greatness” for NFL quarterback Tom Brady?
6. What is the “I-495 Rule” a metaphor for in the text?
7. According to the text, what often happens when we break commitments easily?
8. What does the author suggest is a major takeaway from his life experience, even at nearly seventy years old?
9. What does the author believe is one of the greatest threats to our convictions and character, especially when presented in a nuanced way?
10. What does the West Point Cadet Prayer, quoted in the text, emphasize regarding difficult choices?

Quiz Answer Key

1. According to General McChrystal’s formula, character is the product of convictions multiplied by discipline. This means that both strong beliefs and the discipline to act on them are necessary for character.
2. The author suggests that actions are the primary way people are assessed, as they can be observed and measured, unlike internal thoughts and convictions. While behaviors can be influenced, they are ultimately seen as the most accurate representation of character.
3. The author defines self-discipline as the will of an individual to consistently do what they believe is right. It involves maintaining personal standards and goals, even on seemingly trivial matters.
4. The phrase “Embrace the Suck” is used to describe the choice to accept and find value in difficult or painful situations. It implies a decision to endure challenges without complaining.
5. The author credits Tom Brady’s overwhelming drive, work ethic, and attention to detail as the potential “secret to his greatness.” This suggests that intensity and focus are key factors in achieving high levels of performance.
6. The “I-495 Rule” is a metaphor for having a very small group of people in your life whom you trust implicitly and without question. It represents a deep and unwavering level of personal trust.
7. According to the text, breaking commitments easily becomes a habit. Commitments that are easily abandoned often reset the value placed on all promises in our lives.
8. A major takeaway for the author at nearly seventy years old is wishing he had thought more, been more contemplative about his convictions, and been more deliberate about the person he sought to be.
9. The author believes one of the greatest threats to convictions and character are nuanced situations where it’s tempting to rationalize. This makes it difficult to adhere to one’s principles.
10. The West Point Cadet Prayer emphasizes choosing “the harder right instead of the easier wrong” and not being content with a half-truth. It highlights the importance of making morally difficult choices even when there’s a simpler alternative.

Essay Format Questions

1. Discuss the relationship between convictions and discipline as presented in the text. How does the author argue that both are essential for building strong character, and what are the potential consequences of lacking one or the other?
2. Analyze the author’s reflection on his military career and the pivotal moment that forced him to reconsider his identity and convictions. How did this experience shape his perspective on introspection and the importance of defining one’s beliefs?
3. Explore the author’s views on the role of external factors and personal choice in shaping who we become. Use examples from the text, such as his upbringing, military experiences, or interactions with his granddaughters, to support your analysis.
4. Examine the concept of “living up to our values” as discussed in the text. How does the author suggest we can assess whether our actions align with our professed values, and what are the challenges and pressures that can make this difficult?
5. Discuss the author’s perspective on aging and thinking about the end of life. How does this contemplation influence his view of his remaining time and the kind of person he still aspires to be?

Glossary of Key Terms

• Character: Defined by the author as the product of convictions multiplied by discipline. It represents the intangible essence of a person reflected in their behaviors, motivations, and bedrock values.
• Convictions: The mainsprings of action and the driving powers of life. They are deeply held beliefs that shape perceptions, biases, and behavior, serving as the load-bearing pillars of who a person is.
• Discipline: Specifically, “self-discipline” is defined as the will of an individual to consistently do what they believe is right. It involves maintaining personal standards and aligning actions with convictions.
• Introspection: The act of looking inward and examining one’s own thoughts and feelings. The author suggests that even sincere introspection can be flawed due to blind spots and biases.
• Circumspection: To look around and consider all angles of a situation holistically. The author views this as a more valuable approach than introspection in the pursuit of defining convictions.
• Rationalize: The act of attempting to justify actions or beliefs with plausible reasons, even when they are contrary to one’s values or convictions. The author sees this as a significant threat to character.
• Embrace the Suck: A phrase used to describe the choice to willingly accept and endure difficult or uncomfortable situations without complaining. It implies a positive attitude towards challenges.
• I-495 Rule: A metaphor representing a very small, select group of people whom one trusts completely and without question, even in extraordinary circumstances.
• Values: Fundamental principles or standards that guide a person’s behavior and judgment. The author discusses the importance of living up to one’s values and the difficulty of doing so under pressure.
• Legacy: The impact a person leaves behind after their death. The author reflects on how he hopes to be remembered, particularly by his granddaughters, rather than focusing on traditional measures of success.