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.