Sailing Upwind

Leadership and Risk from TopGun to the Situation Room

  • Subject: Spring 2023 Catalog | Biography & Memoirs
  • Format:
  • Pages:
  • Illustrations:
    46 b/w photos; 4 figures
  • Published:
    April 15, 2023
  • ISBN-10:
  • ISBN-13:
  • Product Dimensions:
    9 × 6 × 1 in
  • Product Weight:
    20 oz
Hardcover $32.95
Member Price $26.36 Save 20%
Book: Cover Type


Sailing Upwind is more than just another memoir of a distinguished former naval officer’s highly diverse career. This book by Admiral James “Sandy” Winnefeld is also intended to offer useful reflections regarding how he accepted and managed risk along the way, as well as a concise description of the qualities one must develop to become a successful leader.

Winnefeld began his career as an F-14 fighter pilot and TOPGUN instructor, commanded an aircraft carrier, and then served in a variety of flag officer billets on the way to becoming the Vice Chairman of the Joint Chiefs of Staff. This book describes in an entertaining and humble manner how that journey unfolded and the lessons he attaches to it.

The reader learns what it is like to become a Navy fighter pilot, and to fly, fight, and takeoff and land from an aircraft carrier – including a harrowing description of ejecting from an F-14 at night far from land. Winnefeld describes the culture of excellence at the real TOPGUN and the Navy’s nuclear propulsion program. He recounts how he learned to lead the men and women who operate at every level of Navy operational command, from squadron to ship to fleet. Finally, the author presents a behind-the-scenes look at how decisions are made at the highest levels of government regarding whether and how those forces will be used, and how they are acquired.

In the process, Winnefeld provides descriptions of how, by challenging existing assumptions and processes and through relentless creativity, he was able to lead change. He reflects on how the risk associated with such changes should be accepted and managed. The title Sailing Upwind—in which a sailboat must be operated against a prevailing force field to make progress in the right direction—is an apt metaphor for the bent for pushing against the system Winnefeld describes throughout the book.

About the Author

Editorial Reviews

“Sandy has not only written a really good book chock full of gripping stories of serving at every level in the military . . . he managed to weave into it an incredibly useful framework for understanding leadership, creativity, and problem-solving. Any aspiring leader will benefit from picking it up . . . and I guarantee they won’t be able to put it down.” — Tim McGraw, country music singer and actor
“Leadership, innovation, problem-solving, and human connection make up the foundation of any successful profession, including the military, as I observed while traveling the world with Sandy on a USO tour. In Sailing Upwind, his engaging and unique voice captures the essence of a remarkable life and career.” —Andrew Luck, former professional football quarterback
“From “Top Gun” to the top of military leadership, Admiral Sandy Winnefeld sailed to record heights of achievement – even for a Georgia Tech Yellow Jacket. Sandy gives us front-row insights into the critical thinking and innovative actions required to move a system slow to change in a different and positive direction. Much more than a memoir of Sandy’s remarkable career, Sailing Upwind provides a valuable guide to living an inspirational life and providing impactful leadership.” —Senator Sam Nunn
“Sailing Upwind is a superb reflection of the life of a leader who really knows how to make things happen. In this book Sandy Winnefeld educates, inspires, and entertains us. He challenges us to embrace the headwinds in our lives. A must-read for anyone who aspires to lead.” —GEN Martin E. Dempsey, USA, (Ret.) 18th Chairman of the Joint Chiefs of Staff
"In, Sailing Upwind, Leadership and Risk from TopGun to the Situation Room, the Admiral dives into leadership principles he learned during his storied career.  It is clear from the pages of this welcome addition to the leadership genre that Winnefeld operated under the notion that leaders are made, not born and that challenging assumptions is learned, not a skill that is just a given." — The Cipher Brief
"This is an autobiography of a naval aviator who rose to become the senior naval officer as vice chairman of the Joint Chiefs of Staff. Naval officers of the late Cold War period and the wars in Afghanistan and Iraq will recognize and identify with his experiences as he describes them. Beginning with NROTC at Georgia Tech, the narrative proceeds through flight training, service as an F-14 pilot, Topgun instructor, and command of a squadron, an amphibious warfare ship, and the mighty USS Enterprise; an aircraft carrier that he took to war as it launched the first strikes of Operation Enduring Freedom. He later commanded a carrier strike group in support of Operation Iraqi Freedom and later the U.S. 6th Fleet and U.S. Northern Command. This book serves well as a guide to how to be a successful officer at all levels."—Seapower Magazine