April 19, 2024
Sailing Upwind is more than 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, and 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 entertainingly and humbly 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 take off 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.
Admiral James A. "Sandy" Winnefeld, Jr. graduated from the Georgia Institute of Technology with a degree in Aerospace Engineering and served for thirty-seven years in the U.S. Navy. He instructed at the Navy Fighter Weapons School, also known as TopGun, and served as senior aide-de-camp to Gen. Colin L. Powell. He commanded a fighter squadron, the amphibious ship USS Cleveland, and the aircraft carrier USS Enterprise. As a flag officer, he commanded a carrier strike group, two NATO commands, the U.S. Sixth Fleet, U.S. Northern Command, and the North American Aerospace Defense Command. He retired in 2015 after serving as the ninth vice chairman of the Joint Chiefs of Staff. Admiral Winnefeld is a frequently published author and a director or advisory board member for several companies operating in a broad spectrum of business sectors. He is a distinguished professor at the Sam Nunn School of International Affairs at Georgia Tech, where he is also a member of the Engineering Hall of Fame. He is a senior Non-resident Fellow at the Belfer Center for Science and International Affairs, John F. Kennedy School of Government, Harvard University. Admiral Winnefeld and his wife Mary co-founded SAFEProject.US, a national nonprofit committed to helping reverse the epidemic of drug overdose fatalities in the United States. He is co-host of the podcast “The Adrenaline Zone.”