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Reflection on Failure By Major Matthew Tweedy, USMC

Plato and Aristotle in Raphael's "The School of the Athens"

Whatever remains of my military service is under a cloud of institutional failure. My 19 years in uniform amount to an 0-2 record. There are few silver linings and no respite in tactical victories. Any deeper meaning fails to assuage this reality. Honesty, though, is a salve. The Global War on Terror (GWOT) is the punchline for future generations, an admonition of the limits of power and the reward of bad strategy. By the year 2100, when the wars are discussed, I suspect any good we did will be buried in the footnotes of books about strategic failure and hubris.

The measure of effective strategy is often revealed in the consequences of its absence. It is easier to diagnose strategic thinking in hindsight than it is to face an uncertain future. One can make forecasts with intimate knowledge of the past, but given the incomplete nature of historical knowledge, being a bibliophile is not enough. We lack wisdom and I’m skeptical we know how to claim it.

I am not a strategist, nor am I wise. I’ve never been in a room where grand decisions are made. I’m not sure I would do better than the men and women who were in the room these past 20 years. It is satisfying to cast stones; blame comes naturally but is ultimately empty. When I consider the would-be great men and women who presided over failure, I recognize myself in all of them.

I’m reminded of the Sword of Damocles - of the weight of responsibility dangling over the heads of executives, independent of whatever motivations and incentives authority manifests. I’ve felt small swords over my head at times and know that what looks easy never is. In war and diplomacy, favorable outcomes generate unintended consequences. No plan is obviously good; it is often the best of bad options and necessarily changes when confronted with reality. The world as it is often stands in opposition to the world we want.

If it were simple to produce strategic thinkers, the world would be full of them. Certainly, the wealthiest and most stable nation states could develop systems of education, coupled with practical experience, to serve the greater good. Except this is not the case. Indeed, it is a safe assumption that few institutions in human history have unvarnished track records of making strategic thinkers. Why?

What I Think I Think about Strategic Thinkers

In a research paper commissioned by the U.S. Army Research Institute, Lieutenant General Paul Van Riper, USMC (Ret), defined strategic thinking this way: “Strategic thinking employs a leader’s wisdom--gained through experience and education—to: assist in selecting the ways and means needed to support the achievement of national policy goals (ends); select the military strategy to accomplish the goals (ends) of national security strategy; and plan for an execute campaigns and operations that advance that strategy… (Van Riper 2013). The vital element of this definition is the introductory qualifier - “a leader’s wisdom”. I will argue that understanding our failure in the GWOT requires us to admit that we have spent too much energy on the wrong word in the phrase “a leader’s wisdom”.

Before I attempt to articulate a reason why it is difficult to produce strategic thinkers, I need to outline a few factors I’ve come to believe about strategists.

1. Many strategic thinkers are unknown and are unlikely to gain recognition because they contribute within a system administered by non-strategists. As such, we cannot know how many there are or if they are good or bad. All we know is we don’t know who they are. This poses a problem when assessing strategy because an organization’s senior leader becomes the face of something he or she did not author.

2. The absence of failure is not evidence of a successful strategy. This suggests that uncontrollable factors (such as Clausewitzian battlefield dynamics) play an outsized role in determining outcomes. Just as a great thinker may be undone by events, an inferior thinker may benefit from them.

Charisma vs. Character

To learn from strategic failure, we must assess our leaders, because whether they authored the strategy or not, they own it. Senior leaders need strategic thinking skills, but we make assumptions about their capacity to think strategically or discount the importance of it. Instead, we are often drawn to other attributes. For instance, leaders must display charisma to inspire, possess traits to win over a room, and earn the trust of subordinates and seniors alike. Possessing these leadership and martial virtues does not guarantee strategic thinking, however, but it does increase popular acclaim.

Charisma and notoriety, either in popular culture or within academic circles, appear inextricably linked to the credibility of a strategic thinker. Fame matters. Even within academia, it is Bezos, Jobs, and Musk who show up in Harvard Case Studies rather than Alfred Kelly (Visa), Peter Pistners (MD Anderson), and Rich Lesser (Boston Consulting Group). General Stanley McChrystal was fired by the Obama Administration with little evidence of strategic success yet rewarded with book deals, high-priced consultancies, and a ceaseless well of cultural credibility. I suspect his post-retirement success has something to do with apocryphal accounts of 3 hours of sleep, one meal a day, and 10-mile morning runs. General James Mattis benefits from similar hagiography. We gravitate towards distinctiveness to anchor memory and explain success. Discipline may be misinterpreted as eccentricities or, perhaps, admired thinkers–like great artists–are unlike the common man. Except the consequences of bad art are not as significant as the consequences of bad strategy.

A leader may be charismatic and possess intact character--I am not suggesting that being revered within popular culture or across the ranks is evidence of poor character. The deficit is within the audience, the aspirants grasping towards greatness with their eyes only. When charisma is valued more than character, deep thinking is vulnerable to pathos and venality. This is not to say character is not valued, merely a recognition that charisma captures our attention and creates shortcuts in reasoning and human development. We study founders and strategic leaders and obsess over what they did and why they did it. We measure the curriculum vitae without considering all the quiet moments that make a man or woman. Oh, this guy graduated from Wharton? I guess I need to graduate from a top MBA program. Steve Jobs studied calligraphy? I need to study calligraphy. This general officer graduated from SAW or NPS? That must be the anointed path. Since even the best biographies cannot tell us what someone was thinking or how well they thought, we place outsized value on what can be observed and measured. This focus on action creates a cult of imitation; the worship of eccentricity creates mimics. All unoriginal.

Goals vs Effects

We live in another era where the “best and brightest” failed to think strategically. Our credentialed elites–all products of the best educational institutions–did not meet expectations. We should cringe when considering the collective hours of critical thinking classes and books the top military and civilian leaders theoretically absorbed over the past 20 years. It did not produce wisdom at the highest levels. The essential question is not how or who thinks critically. But rather: Why can some do it in the first place?

In the utilitarian telling, education exists to maximize human flourishing by hitting various benchmarks within the educational system. The goal is material – stuff and things and status, what I term “effects.” Across the board, we see the effects of graduating high school are better than dropping out. The effects of attaining a master’s degree include faster and better promotions and a higher salary. Institutions that measure effects (credentials) can claim goals are met empirically (which is very reminiscent of body counts in Vietnam).

One need only read a recent message from Sergeant Major Troy Black, Sergeant Major of the Marine Corps, to see this confusion firsthand. He wrote about the role of the United States Naval Community College, noting how it will help sailors and Marines “...form a foundation for lifelong learning and developing critical thinking skills...” This noble sentiment means little when pursuing education. The Sergeant Major is measuring success by effect only. Terms like “lifelong learning” and “critical thinking” are ubiquitous and buzzy, but even if he is serious, Sergeant Major Black is still talking about the effects of education.

Critical thinking is an effect, not a goal. It is a description of a common human act. Thinking is the action while critical thinking is the skill. We all think, and some are better at it than others. If we spend time worrying about the skill without interrogating the act itself, we will know little of either (Hitz). This is of particular importance when considering professional military education, the source of our strategists. Recalling LtGen Van Riper’s definition, the successful strategic thinker, beyond any alternative adjective, must be wise. This raises critical questions: Where are our wise men and women and what must we do to discover and nurture them? Answering these questions begins with recognizing the proper goal of education.

The goal of education is the right ordering of human life. This classical view posits that the development of virtue and excellence manifests as character and from character comes wisdom. Put another way, education exists to help us pursue our full capacity to know and to be. This stems from an understanding that humans are inclined to ponder fundamental questions about existence, justice, and the right way to live.

This is not to say that all strategic thinkers across time and space possess exemplary character. Rather, character provides a means by which an individual cultivates wisdom. Perhaps divorced from classical philosophy, or rather any school of philosophy, a common trait of strategic thinkers is that they go beyond a desire to know for knowledge’s sake. Instead, they are driven by the urge to wrestle with questions common to all humanity, the deep questions beyond our grasp.

It was easier for me to accept the necessity of struggle to grow in understanding after reading Mortimer Adler’s “Invitation to the Pain of Learning.” Published in 1941, Adler critiqued the education provided by his era’s school systems as “frothy and vapid.” Rather than cultivate the character and virtue of students, Adler believed schools prioritized skill attainment and entertainment. The thrust of his argument is that the ends of education were not aligned with the desired effects of school, a much better way of saying schools valued charisma over character, mistakenly measuring effects.

Our era is not unique, and reform is possible. At the risk of overusing this example, the Prussian Military Reform offers a useful parallel to our present paucity of strategic thinking. My preferred interpretation of the German word bildung is the “perfectibility of character through education.” Gerhard von Scharnhorst made bildung the central tenet of his academies. His most famous student, Carl von Clausewitz, referred to him as “the father of my spirit” (White). The mere insinuation that education is deeper than a mental pursuit, once obvious to our classical forebears, indicates we are missing something. Scharnhorst and Clausewitz were products of the philosophical energy of Enlightenment thinkers like Kant, Voltaire, and Rousseau. Intellectual life, even applied to the profession of arms, was intertwined with the deeper questions of theology, metaphysics, ethics, science, and mathematics. It is upon grappling and struggling with deeper things that humans can ascertain the limits of their own understanding. To do this, and do it earnestly, leads to wisdom. Properly understood, the goal of successful education is wisdom. Everything else is an effect of this pursuit, a by-product.

Our age is not devoid of wise men and women. One needs only to hear a few apocryphal accounts of Boyd wrestling with Clausewitz to recognize he was consumed by fundamental questions. Boyd used philosophy, history, mathematics, and science to make sense of war–just like Clausewitz before him. It is easy for me to imagine Boyd, manic and ravaged by insomnia, pouring over On War until he arrived at the interdisciplinary emergence that resulted in “Patterns of Conflict” and the OODA Loop.

To summarize: We struggle to produce strategic thinkers. This deficiency relates to a confusion between effects and the goal of education. The goal of education is the right ordering of human life. A successful education produces an individual with well-formed character. An individual with well-formed character can achieve wisdom. Wisdom manifests in those who grapple with the deepest questions of life. Individuals pursue these fundamental questions through theology, metaphysics, ethics, mathematics, and science. To ask questions in one domain necessitates consideration of some or all domains, which inculcates the required skills for interdisciplinary emergence (Hitz).

Wisdom cannot be taught; it must be pursued. The professor, leader, mentor, and parent do not impart wisdom. They model a path to wisdom and serve as a creative spark for those seeking it. There are exceptional people with innate advantages and natural curiosity who emerge with little guidance or structure, but we often embrace their charisma and mimic their attributes without asking the deeper questions that address why they succeed where others fail. We lifehack Andrew Marshall by embracing open office floor plans; we take calligraphy classes thinking it is a cheat code to be like Steve Jobs. We confuse a well-produced TED talk with the agony and ecstasy of reading The Brothers Karamazov.

A Radical Suggestion for Reform

Mark Twain said that “the man who does not read has no advantage over the man who cannot read.” Does that mean all reading is equal? Of course not. In the absence of experience, we learn vicariously. Books are the best option we have, but there are chasms of quality across published works. To improve the character of our thinkers and enable them to achieve wisdom, we must read The Great Books. We should embrace Adler’s suffering and pursue the fundamental questions by reading the answers of masters.

Here’s my radical suggestion for reform: If the Marine Corps deployed 15 officers to a lakeside retreat for three months and took away their phones and issued them kettlebells; a journal; a trunk containing works from Aristotle, Aquinas, Euclid, Voltaire, Kant, Nietzsche, Dostoevsky, Homer, and Shakespeare; and asked them to do nothing but read and reflect--perhaps with a journal or in discussion with peers, I think their collective wisdom would grow faster than participating in any existing program of record.

My suggestion is unlikely to happen, though I think I could convince many Marines of its merits. I used to joke as a young enlisted man that you could tell just by looking what Marines had killed a man in combat. It was a lighthearted way of processing experience and sharing it within a community. Years later, I still think there is an air of truth to it. Killing changes; there is something in the eyes. For some, the change manifests as wisdom–old eyes in a young body. It is not the type of wisdom you want or wish on someone, but the change occurs, nonetheless. For others, the transformation debilitates; the eyes become animalistic. Trauma consumes. Killing in war goes beyond the simple knowledge of experience. It is deeper and ancestral–a link to the dawn of human existence. I use this anecdote to suggest that transformation is the inevitable outcome of collective strategic failure. To understand failure requires grappling with deeper questions to illuminate wisdom. If we memory-hole the traumatic experience of failure, the transformation will still occur. We just abdicate our claim on the course it takes. It’s not that we become closed off from wisdom, but that we open ourselves up to folly. The trauma of the strategic failure consumes.

I see trauma in the weeks following our withdrawal from Afghanistan. Our strategic class is shaken and lurching towards distraction. Some are tempted to forget, to move on to bigger things like China and the emerging bi-polar world. Others seem intent on avoiding accountability, even if only symbolically. This folly dooms us to repeat mistakes. We need to question everything. We need to seek insights from the past, not cope with promises of the future. Chapter 4 of Charles White’s The Enlightened Soldier, titled “The Aristocracy of Education,” describes Scharnhorst’s academy. We need to enlighten the aristocrats–the officers–by rejecting the effects of education and embracing the goal of it. Wisdom requires grappling with the deeper questions of failure, not distracting ourselves with new programs or policies.

Which brings me to a different strategic class from the recent past, one that included people like Colonel John Boyd, General Al Gray, General Tony Zinni, and Secretary Colin Powell. These were men who did not forget, who refused to stop looking at the failure of Vietnam. They were skeptics first and reformers second. Their skepticism was not masochism. It was their pathway to grapple with fundamental questions beyond a uniform and equipment set. Maneuver warfare and mission command are nothing without metaphysics and ethics. Time and space, tempo, friction, and uncertainty are concerned with the nature of things–with knowing and being. Trust requires an ethical framework; commander’s intent is diminished without intact character. Alas, the thinkers of the 1980s left an incomplete project and some of their successors fell to mimicry. Perhaps it was always impossible to complete. Perhaps any future American strategic victory will be material because Americans are materialists and mission command and maneuver warfare work best for underdogs with hustle borne from the lack of material power. We should question maneuver warfare, too.

If you wear a military uniform, you have a losing record. That alone must motivate you to action. I am reminded of the wooden sign mounted in Mitchell Hall, the home of the Marine Corps’ Infantry Officer Course. Engraved in the wood is a quote from Thucydides: “He is best who is trained in the severest school.” Some members of the post-Vietnam strategic class endured the severest school and chose, by their wisdom, to confront failure for the good. They did not reach for distraction nor avoid the lessons of losing and their efforts yielded reform and meaningful contributions to the profession of arms. We must do the same with Afghanistan and Iraq. Until we do, I am not optimistic about the future. I am confident of my own skepticism. That is the least I can do.


United States Naval Community College, [@USNCCollege]. (2021, September 1)

Charles Edward White, The Enlightened Soldier: Scharnhorst and the Militärische Gesellschaft in Berlin, 1801-1805 (Westport, CT: Praeger Publishers, 1989)

Hitz, Zena. (Host). (2021, August 16). Way Towards Wisdom. In Thomistic Institute. The Thomistic Institute.

Wolters, H. M., Grome, A. P., & Hinds, R. M. (2013). Exploring strategic thinking: Insights to assess, develop, and retain strategic thinkers. Applied Research Associates Inc., Fairborn, Oh.

*See Chapter 1: The Identification and Education of U.S. Army Strategic Thinkers, Paul K. Van Riper

12,868 views10 comments


Easily the best thing I've ever read. I've needed something like this since the fall of Kabul. Something meaningful and to set my azimuth too. Thank you, from the bottom of my heart for writing this.


And who knows who has trained in the severest schools? You mentioned a number of gentlemen who I’ve known. Gen Berger and I were in the same squad in TBS. He’s a genuinely good guy and seems to be exactly the same guy as before, which is of course, impossible. Your first commenter, Eric Walters, taught me enough IPB in an hour to win in a force-on-force MCCRES serving with Frank MacKenzie as the S3. I never went to CGSC, much less SAW but nonetheless wound up doing strategy for the HOA on the JS. Strategy falls apart at the civil-military level in my experience. Ends and means don’t match reality, generals aren’t politically astute and politicians aren’t militarily astute…


Overall reaction to the comments, which I only read after making my own...

Gentlemen, I would like to submit to you all that the time has come to acknowledge that all the wondrous work we've done with the varied and sundry military educational efforts undertaken by all branches over the last few generations...? It hasn't actually worked.

The evidence is all around us, irrefutable in nature, visible to all of us who can steel ourselves to look to observe honestly. We have a military that screwed up what should have been an easily-managed withdrawal from Afghanistan, an Army which has produced a general officer who felt it was more important to get an illegal war trophy back to the US…


Tom Grow
Tom Grow
Nov 10, 2021

Enjoyed this, thank you. You mention the link between character and wisdom much. If memory serves, the best classical definition of wisdom I’ve read is: “ Wisdom is that perfect knowledge that directs the will to obey the commandments. “ Recall that those considered wise were most often those unfettered with the selfish distractions the rest of us plebes deal with.


I read this, and I'm reminded of a work I encountered a few years ago, a lecture conducted by Dr. Leonard Wong, a retired LTC working now for the US Army War College's Strategic Studies Institute. The lecture is entitled "Lying to Ourselves: Dishonesty in the Army Profession", and is found here at YouTube, for now:

I'm a retired Army senior NCO, and upon encountering this lecture of Dr. Wong's, I was viscerally disturbed. Why? Because I'd always subconsciously assumed that the issues he'd raised with the systemic structures that encourage the formation of lying within the Army were things that I thought the leadership <i>knew</i> about, and understood.

Watching that video, and seeing the reaction of the audience,…

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