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
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.
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Leadership & Command
Leadership is easy when conditions are ideal. This category was tested in environments where failure had real consequences.
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Special Operations, Intelligence & Conflict
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.
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Military History & Strategy
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.
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Technology, AI & the Future of Conflict
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.
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Wisdom
The title above captures it all. Heed this knowledge or fall into antiquity.
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Business, Sales & Building
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.
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Literature & the Creative Side
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.
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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.