Why this book: Selected by the SEAL book club as our selection for summer of 2025. I and many of us had worked with Stan McChrystal in our careers. 

Summary in 3 Sentences:  A thoughtful meditation on values that help drive the decisions we make and how we live our lives – but McChrystal does it in the first person. It is very autobiographical – the wisdom he’s accrued over a full and fascinating lifetime of training and leading soldiers in combat.  But he doesn’t dwell on combat – he focuses on values he also brings in his experience coaching CEO’s in the civilian sector, as well as key life issues such as marriage, raising children, friendship, losing loved ones, accepting and  preparing for one’s eventual death. 

My impressions:  The title describes the book well – the choices Stan McChrystal has made in his life that define him and his life. It is indeed part memoir, part reflection on his decisions, part philosophy and wisdom accrued during a long, eventful and full life. It isn’t over – he is 72 years old with (presumably) many more years to live – I’d be interested in addendum in 10 or 15 years.

He is well known in military circles for having led a very successful campaign against Al Queda in Iraq and subsequently been given command of US forces fighting the Taliban and other terrorists in Afghanistan.  His book Team of Teams (my review here) provides a valuable  description of his groundbreaking initiatives to increase the success of our efforts to combat Al Queda in Iraq.  This book is more personal – how he has personally dealt with the challenges of not just leadership, but life in general – and he offers insights about leadership as well as character, how they are reflected in his decisions, both as a military leader and as a husband, father, and citizen,  and how they all overlap.

He begins with the impact of what led to his decision to resign from his position of leading US Forces fighting the Taliban in Afghanistan.  This was the first significant and dramatic failure in his life – and how he dealt with it.  He also offers other examples from his career where he felt he fell short and what he learned from those examples.  

His message can be muddy – intentionally so, since there is no easy formula for defining and developing good character.  As one of my philosophy mentors (Dr George Lucas) once told me, philosophers and thinkers have been arguing for millenia over three questions: What is good character?  Can it be developed? If so, how?   McChrystal doesn’t provide a pat formula for good character, admits that it’s messy, often can be situationally dependent, but he always emphasizes that it is important, that we need to think about our own character, and realize that any and every decision we make contributes to and says something about our character. This should be a consideration that should always be part of one’s decision making process. 

He points out that much that affects us in our lives is beyond our control.  But how we deal with circumstances and what our decisions say about our character are two very important factors that only we control.  Both the existential and stoic philosophies emphasize that “what is important is not what happens to us. What is important is how we deal with what happens t us.  Our character is not a function of what we say or believe – it is a function of what we do and how we behave.  He argues that our character defines the essence of who we are.  He notes that our reputation reflects what other people think of us; our character reflects who we really are – what the angels think of us.

He argues that it is important that we think and think deeply about our values and convictions. What do we most value? What are the things, behaviors values most important to us?.  But our true values are not what we think or say they are, rather they are reflected in how we behave and act, the decisions we make.  Creating and maintaining alignment between what we believe are our values and what we do and how we behave is a lifelong project, and all (or nearly all) of us fail sometimes.  It is part of being human.  Discipline and commitment are necessary, if  constantly improving our character is important to us, 

He offers us examples of when he believed his character fell short.  McChrystal is much more disciplined than the vast majority of people I know, but he humbly admits to having failed many times and how he still struggles sometimes with behaving in a way that is consistent with his values.  But he argues that is part of the point: If character is important to us,  we will always struggle to some extent with aligning our decisions and actions with the values we profess to believe in.  

A couple of chapter titles are clues to some of his more intriguing discussions:   “Opportunity or Opportunism,” “On Patriotism,”  “Anger and Frustration,” “Monuments.”  In each, he shares personal stories and perspectives, all of which are thoughtful, many are surprising.  

A couple of things I didn’t see in his book that I’d liked to have seen.  He didn’t address the Pat Tillman controversy in which the role he played remains somewhat controversial,  and which continues to bubble in the media.  I’d also have liked him to address the cultural dimension of character.  Stan McChrystal’s views on character and values have a uniquely American flavor – how much of his definition would fit in very different cultures like Asian or Middle Eastern?  In fact, even within the US – his vision and idea of character have a strong US Army Ranger flavor  – certainly understandable – that’s his background and frame of reference and is a bit more strict than works for me.   Does that ideal work for most of  Americans?  I suspect he would respond that his message is not that we follow his version of good character, but that we’ve thought about it, have identified our values and strive to do our best to live by them.  

Given the tough decisions he’s had to make, I would also have liked for him to have addressed the “Dirty Hands” challenge that political and military leaders (and perhaps all leaders) face when given a choice between multiple bad options, all with bad consequences, but having to pick one.  One cannot (or at least in my view,  should not) say simply, “too bad.  The ends justify the means,” and then feel ok. The wrong and bad results remain, and the leader is still accountable for them.  

His book succeeded in challenging me to reflect on my own values, behavior and character.  I liked his personal stories, his openness and humility,   and how he made this book a personal reflection vice an academic study.