The Captain's Reading List

93 books that changed how I lead, decide, and operate.

Two careers. Eight categories. One working library.

I get asked the same question in every boardroom, at every speaking engagement, and across every platform we post on: what should I be reading? Here is my raw list of the actual books I have returned to across two careers in Naval Special Warfare and in the technology executive world. Each one is on this list because it changed something about how I think, decide, or operate. Start where you feel the pull. The books that change you are rarely the ones you expected. — Capt. Brian G. Cunningham, USN (Ret.)

Decision-Making & Strategic Thinking

Category 01 · 11 books

Most people think they have a decision problem. They have a structure problem. These books give you the frameworks that separate reactive thinking from deliberate judgment.

  1. 01
    Daniel Kahneman

    The definitive map of how the brain actually makes decisions — and where it systematically fails. Required foundation.

  2. 02
    Nassim Nicholas Taleb

    On the hidden asymmetries that separate people who bear consequences from those who do not. Permanently changes how you evaluate advice.

  3. 03
    Nassim Nicholas Taleb

    Why rare, high-impact events dominate outcomes — and why we consistently underestimate them. Essential for risk thinking.

  4. 04
    Roger Fisher

    The original negotiation framework. Every high-stakes conversation is a decision point. Read before you enter any room.

  5. 05
    Bent Flyvbjerg

    Why major projects fail and the surprisingly simple factors that make them succeed. Changes how you scope and sequence decisions.

  6. 06
    Greg McKeown

    The disciplined pursuit of less. A framework for cutting what does not matter so the things that do get everything.

  7. 07
    Joseph McCormack

    How to communicate with precision and respect for the decision-maker's time. Short. Immediately applicable.

  8. 08
    Gen. Stanley McChrystal

    A practical framework for identifying, classifying, and managing risk — from the general who rewrote how the U.S. military operates.

  9. 09
    Paul Arden

    Counterintuitive thinking as a competitive edge. Short, unconventional, and consistently overlooked. One of the best quick reads on this list.

  10. 10
    Stephen M.R. Covey

    Trust as a measurable variable in organizational performance. Slower trust \= more cost. Faster trust \= better decisions.

  11. 11
    Mihaly Csikszentmihalyi

    Leadership, flow, and meaning-making in organizations. Why purpose drives better decisions than incentives alone.

Leadership & Command

Category 02 · 10 books

Leadership is easy when conditions are ideal. This category was tested in environments where failure had real consequences.

  1. 01
    Gen. Stanley McChrystal

    How JSOC transformed from a rigid hierarchy into a networked, adaptive fighting force. The model for leading in complexity.

  2. 02
    Gen. Stanley McChrystal

    Thirteen leaders across history examined not as myths but as real human beings navigating impossible situations.

  3. 03
    Gen. Stanley McChrystal

    McChrystal's memoir. Rare candor about what leading at scale actually requires — and what it costs.

  4. 04
    Anton Myrer

    The novel passed from general to general for decades. Two officers, two paths, one right answer about what leadership actually demands.

  5. 05
    Christopher Kolenda

    Essays on the theory and practice of military leadership from those who have actually done it.

  6. 06
    Wess Roberts

    Deceptively simple. The principles are timeless. A short read that lands harder than most longer ones.

  7. 07
    James Kerr

    How the most successful sports team in history builds culture, identity, and standards that outlast any individual.

  8. 08
    Adm. William H. McRaven

    The man who planned the bin Laden raid on what he has learned about leadership in a career defined by impossible missions.

  9. 09
    William P. Mack & Thomas McNally

    The foundational reference for naval service. Operational grounding for anyone in or studying maritime leadership.

  10. 10
    Geoff Watts

    From good to great servant leadership. The operational framework for high-velocity team performance.

Special Operations, Intelligence & Conflict

Category 03 · 10 books

Eleven deployments across four combatant commands gave me a library of lived experience these books validate and extend. This category covers the operators, the intelligence professionals, and the strategists who operate where the cost of a wrong decision is paid in lives.

  1. 01
    Benjamin H. Milligan

    The definitive history of how Naval Special Warfare was built. Where the SEAL ethos actually came from.

  2. 02
    Dick Couch

    Inside BUD/S — the training that produces Navy SEALs. An unflinching account of selection and what it produces.

  3. 03
    Dick R Couch

    Vietnam-era SEAL operations. The tactical origins of the force.

  4. 04
    Stephan Talty

    The greatest rescue mission in Navy SEAL history. A masterclass in courage under conditions that had no good options.

  5. 05
    PhD Chris Frueh

    The psychological cost of sustained combat exposure — and what it means for the operators, their families, and the institutions that employ them.

  6. 06
    H.R. McMaster

    How the Joint Chiefs failed to challenge LBJ's Vietnam strategy. The most important book on civilian-military decision-making ever written.

  7. 07
    Lawrence Wright

    How al-Qaeda built itself while U.S. intelligence agencies failed to share what they knew. A study in catastrophic institutional decision failure.

  8. 08
    Tim Weiner

    The unvarnished history of the CIA's most consequential failures. Essential for understanding intelligence as an instrument of policy.

  9. 09
    Ali Soufan

    From the FBI agent who extracted more from high-value detainees than anyone — using rapport, not coercion. A study in human intelligence.

  10. 10
    Dave Grossman

    The psychological cost of learning to kill in war. Uncomfortable, necessary, and far more nuanced than its title suggests.

Military History & Strategy

Category 04 · 18 books

History is the largest dataset available for studying leadership and strategy under real consequences. These are case studies in how individuals and organizations perform when the environment is unforgiving and the margin for error is zero.

  1. 01
    Steven Pressfield

    The Battle of Thermopylae through the eyes of the Spartan warrior culture. Fiction that contains more truth about commitment than most nonfiction.

  2. 02
    Sun Tzu

    The original strategic framework. Read it a dozen times — each time in a different role — and you will find something new each time.

  3. 03
    Carl von Clausewitz

    The foundational theory of war as a continuation of politics. Dense, important, and foundational to everything that came after.

  4. 04
    Robert Greene

    A systematic breakdown of offensive and defensive strategies drawn from military history and applied to modern competition.

  5. 05
    Ian W. Toll

    War at sea in the Pacific, 1941-1942. The first year of the most consequential naval campaign in history.

  6. 06
    Ian W. Toll

    The Pacific War 1942-1944. The turning point told with remarkable operational detail.

  7. 07
    Rick Atkinson

    The War in Western Europe, 1944-1945. The third volume of the Liberation Trilogy and perhaps Atkinson's finest work.

  8. 08
    Rick Atkinson

    Three volumes covering the Allied campaign from North Africa to Germany. The definitive narrative history of WWII in the West.

  9. 09
    Rick Atkinson

    West Point class of 1966 through Vietnam and beyond. A portrait of what military service extracts from the men who answer the call.

  10. 10
    Rick Atkinson

    The Persian Gulf War, told from the inside. The operational and strategic decisions behind the first major post-Cold War conflict.

  11. 11
    Michael Dobbs

    Thirteen days in October 1962\. The best account of how the world came within hours of nuclear war — and who held the line.

  12. 12
    John Wukovits

    Evans Carlson and his WWII Marine Raiders — the precursors to modern Special Operations forces.

  13. 13
    Patrick K. O'Donnell

    The untold story of America's first covert operators in WWII. The origins of clandestine warfare.

  14. 14
    Jamil Ahmad

    Fiction set on the Afghan-Pakistani frontier. No book I have read better captures the human terrain that defines modern conflict.

  15. 15
    Carter Malkasian

    The Anbar Awakening — what really happened in Iraq's most violent province and what it means for counterinsurgency doctrine.

  16. 16
    William Dalrymple

    The First Anglo-Afghan War, 1839-1842. The strategic disaster that every general who entered Afghanistan should have read first.

  17. 17
    Thomas Powers

    The final years of the Lakota resistance and the assassination of one of history's greatest unconventional warriors.

  18. 18
    George Packer

    America in Iraq — what happened when idealism met the actual country. The best civilian account of post-invasion Iraq.

Technology, AI & the Future of Conflict

Category 05 · 8 books

My second career has been at the intersection of artificial intelligence, national security, and advanced computing. These books define the terrain that every serious leader needs to understand, because technology is no longer a support function. It is the battleground.

  1. 01
    Azeem Azhar

    How the next digital revolution will rewire our economies, our societies, and the nature of war. Essential for anyone leading in the tech era.

  2. 02
    Kate Crawford

    Power, politics, and the planetary costs of artificial intelligence. The critical counterweight to AI optimism.

  3. 03
    P.W. Singer

    How information warfare has become the dominant battlefield. Mandatory reading for anyone building a public presence.

  4. 04
    Christian Brose

    How America is losing its military-technological edge — and what it will take to get it back. The most important national security book of the last decade.

  5. 05
    Eli Berman

    The information revolution in modern conflict. How data changes what we know, what we target, and how we win.

  6. 06
    Raj M. Shah

    How the Pentagon and Silicon Valley are — and are not — working together to build the next generation of defense capability.

  7. 07
    David Kilcullen

    The coming age of the urban guerrilla. Where future conflict will be fought and why our current frameworks are inadequate.

  8. 08
    David Kilcullen

    Fighting small wars inside big ones. The operational theory behind modern counterinsurgency from one of its leading practitioners.

Wisdom

Category 06 · 12 books

The title above captures it all. Heed this knowledge or fall into antiquity.

  1. 01
    Marcus Aurelius

    The private journal of a Roman emperor who ran an empire during plague and war. The original high-performance self-discipline document.

  2. 02
    Robert Greene

    A systematic study of the predictable patterns in human behavior. Read it to understand yourself. Read it again to understand everyone else.

  3. 03
    Robert Greene

    The laws of power, documented across history. Study it not to exploit them — to recognize when they are being used on you.

  4. 04
    Héctor García

    The Japanese concept of a reason for being — and why purpose is the most durable performance advantage. Short, clarifying, and repeatable.

  5. 05
    Sanjay Gupta M.D.

    The neuroscience of brain health and cognitive performance across a lifetime. Practical, evidence-based, and underread.

  6. 06
    Mihaly Csikszentmihalyi

    What creative mastery actually looks like in practice. How the best thinkers in every domain structure their work and their lives.

  7. 07
    Bill Burnett

    A design-thinking framework applied to career and life decisions. One of the most practically useful books on this list.

  8. 08
    Jared Diamond Ph.D.

    Why some civilizations dominated others — geography, biology, and the deep history of human inequality. The macro frame for everything.

  9. 09
    Jared Diamond

    How nations survive existential crises. Twelve case studies in national resilience. Directly applicable to organizational turnarounds.

  10. 10
    Jared Diamond

    How societies choose to succeed or fail. The pattern of civilizational collapse has never been more relevant.

  11. 11
    Thomas Paine

    The pamphlet that started a revolution. A masterclass in clear argument under conditions where the stakes are irreversible.

  12. 12
    Daron Acemoglu

    Inclusive vs. extractive institutions — why some countries grow and others collapse. The most important economics book of the past 20 years.

Business, Sales & Building

Category 07 · 6 books

Step into a world where you build the structure yourself. These are the books that accelerate that transition, and the ones I hand to any high-performer making the same move.

  1. 01
    Eric Ries

    Build, measure, learn. The operating framework for moving fast without building the wrong thing at scale.

  2. 02
    John McMahon

    Proven lessons from a five-time CRO. The most operationally rigorous sales leadership book written.

  3. 03
    Rand Fishkin

    A painfully honest account of building a startup. What the glossy founder narrative omits and why it matters.

  4. 04
    George S. Clason

    Financial principles through ancient parables. Timeless, simple, and more actionable than most modern personal finance books.

  5. 05
    Gino Wickman, Mark C. Winters

    The One Essential Combination That Will Get You More of What You Want from Your Business.

  6. 06
    Malcolm Gladwell

    The power of thinking without thinking, and the conditions under which rapid judgment succeeds or fails.

Literature & the Creative Side

Category 08 · 6 books

The best operators I have known read Hemingway. This is not incidental. Literature trains a different kind of intelligence — specifically the ability to sit inside ambiguity, to feel the weight of a decision from the inside, to understand human beings as they actually are rather than how systems need them to be.

  1. 01
    Ernest Hemingway

    A man, a fish, and everything it means to go beyond the limit of what you thought you could endure. Read it in one sitting.

  2. 02
    Ernest Hemingway

    War, love, and the moral weight of an impossible mission. Hemingway at his most human.

  3. 03
    Ernest Hemingway

    The cost of war on the individual — told with the restraint that makes it permanent.

  4. 04
    Ernest Hemingway

    The original portrait of what happens to men when the defining experience of their generation is over. Still the most accurate.

  5. 05
    Ernest Hemingway

    The full range. Read "A Clean, Well-Lighted Place" and "Hills Like White Elephants" first.

  6. 06
    Walt Whitman

    American poetry at its most expansive. On this list because the best operators have always made room for beauty alongside the operational.

Coming Soon

Ready to build the system?

Every book on this list sharpens one part of your thinking. The Decision Playbook is how you put it all to work as a repeatable operating system for making better calls when it actually matters. From The Capt & Jess.