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Sailing Upwind: Leadership and Risk from TopGun to the Situation Room
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.
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.
352 pages, Hardcover
Published April 15, 2023
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Displaying 1 - 5 of 5 reviews
May 25, 2023
Many military officer biographies fail to capture the essence of leadership encapsulated by that officer’s career. Sailing Upwind is a notable exception! Former Vice Chairman of the Joint Chiefs of Staff (VCJSCS—second highest-ranking US military officer), Admiral Sandy Winnefeld set out to write this book because he “wanted to pass along what [he] learned about problem solving, risk management, and, above all, leadership through the lens of the diverse and exciting career through which [he] was privileged to sail.” And thus, the title of the work reflects his approach to pushing as close as possible to the edge of risk while maintaining control, just as a sailor tacks into the wind without spilling the energy generated by the sails.
Winnefeld’s 37 years in uniform included nine extended overseas deployments, during times of war and peace spanning both the Cold War and operations in the Middle East. And as the son of a retired Navy rear admiral, the younger Winnefeld levied high expectations upon himself to become somebody. And somebody of military excellence and prominence he became!
Winnefeld thought of going to the Naval Academy at Annapolis like his father, who graduated in the Class of 1951, however, chose instead to take a Navy Reserve Officer Training Corps (NROTC) scholarship to Georgie Tech, graduating and commissioning as an ensign with the class of 1978 and majoring in aerospace engineering. Always desiring to be a naval aviator, Winnefeld pursued that path. As his path unfolds and his career advances, readers become witness to history. Early in his student flying career we witness the Iran hostage crisis through his eyes as he is learning to fly F-14 Tomcats. Aviators will be particularly fond of these stories. For example, one of the radar intercept officers (RIO) Winnefeld flew with was also the RIO for Vietnam Ace Randy Cunnigham, and the parallels to excellence jump off from there. Winnefeld had the good fortune, as one looks back in time, to be a TopGun instructor in Miramar, CA when the movie of the same name came out. The stories here are surreal for those who lived through this era. I was completing my freshman year in college in Air Force ROTC when this movie came out and it was an inspiration in becoming a pilot for all aspiring military aviators.
Winnefeld’s writing style is very readable. Without taking himself too seriously, his humanity and humility entice readers to keep turning the pages. He pokes fun at institutions and himself, often, and you can see the struggle he has with events most military members and their families encounter such as assignments, moving, and extended time away from home.
An enduring strength of Winnefeld’s biography is that besides just telling us about his exceptional career, he shares his leadership lessons and insights with us in the form of five Anchors interspersed throughout the book. Delivered at key junctures of his career, these include Lead Yourself, Lead People, Lead Organizations, Lead Execution, and Lead Change. A short two-to-three-page summation of his thoughts on each of these Anchors anchor each section. The collection of these pithy and useful sections parallel the levels of responsibility Winnefeld accrues during his career and rise through the ranks. Some of the lessons he learned from others, such as Colin Powell, whom he served as an aide-de-camp, and some he came by and adopted as his own because they suited his style.
Ultimately, this biography will stand tall amongst others written during the same era. I personally found it readable, realistic and with application to my own professional and personal life, and I believe other readers will too.
Winnefeld’s 37 years in uniform included nine extended overseas deployments, during times of war and peace spanning both the Cold War and operations in the Middle East. And as the son of a retired Navy rear admiral, the younger Winnefeld levied high expectations upon himself to become somebody. And somebody of military excellence and prominence he became!
Winnefeld thought of going to the Naval Academy at Annapolis like his father, who graduated in the Class of 1951, however, chose instead to take a Navy Reserve Officer Training Corps (NROTC) scholarship to Georgie Tech, graduating and commissioning as an ensign with the class of 1978 and majoring in aerospace engineering. Always desiring to be a naval aviator, Winnefeld pursued that path. As his path unfolds and his career advances, readers become witness to history. Early in his student flying career we witness the Iran hostage crisis through his eyes as he is learning to fly F-14 Tomcats. Aviators will be particularly fond of these stories. For example, one of the radar intercept officers (RIO) Winnefeld flew with was also the RIO for Vietnam Ace Randy Cunnigham, and the parallels to excellence jump off from there. Winnefeld had the good fortune, as one looks back in time, to be a TopGun instructor in Miramar, CA when the movie of the same name came out. The stories here are surreal for those who lived through this era. I was completing my freshman year in college in Air Force ROTC when this movie came out and it was an inspiration in becoming a pilot for all aspiring military aviators.
Winnefeld’s writing style is very readable. Without taking himself too seriously, his humanity and humility entice readers to keep turning the pages. He pokes fun at institutions and himself, often, and you can see the struggle he has with events most military members and their families encounter such as assignments, moving, and extended time away from home.
An enduring strength of Winnefeld’s biography is that besides just telling us about his exceptional career, he shares his leadership lessons and insights with us in the form of five Anchors interspersed throughout the book. Delivered at key junctures of his career, these include Lead Yourself, Lead People, Lead Organizations, Lead Execution, and Lead Change. A short two-to-three-page summation of his thoughts on each of these Anchors anchor each section. The collection of these pithy and useful sections parallel the levels of responsibility Winnefeld accrues during his career and rise through the ranks. Some of the lessons he learned from others, such as Colin Powell, whom he served as an aide-de-camp, and some he came by and adopted as his own because they suited his style.
Ultimately, this biography will stand tall amongst others written during the same era. I personally found it readable, realistic and with application to my own professional and personal life, and I believe other readers will too.
July 24, 2023
Adm. Winnefeld presents a detailed synopsis of his storied career starting with graduation from Georgia Tech in Engineering. Flight school and selection to the famed F-14 Tomcat Community. Through his career he has transversed the earth. He's lead fighter squadron in the Middle East as a pilot. Served as an aid to Colin Powell. Skipper on the Big "E". Each step along the way provided steps that moved him both in Leadership roles and ranks. As a writer he provides the reader insight into some of the critical thinking behind the military through his various roles and some of the issues we've seen over the past 30 years. Amazing near the end of the book he states that often the military is narrow focused in how they approach things. Remanding unwilling to adapt or change as necessary. To me I reflected back how militaries fought prior to the Revolutionary War where armies would face each other and fight. The Revolutionary war changed that thinking. The military has become the British, unwilling to change. He retired as VCJCS a four Star billet. It was a very interesting read, hard at times due to some technical information. But is has a lot of Leadership insight throughout.
June 10, 2023
This book did not disappoint! I appreciated Admiral Winnefeld's format with leadership principles then how they applied in the real world (something often missing in leadership books that promote a theory or idea). Admiral Winnefeld was one of my commanding officers on USS ENTERPRISE, and it was interesting to reflect on that time with the added insight of events from his perspective. Highly recommended if you want to learn from one of our most recent leaders about decision making and leadership in our divisive times.
July 6, 2024
Amazing story on leadership and career of an impressive naval officer. There was an opportunity missed to weave in more of his leadership principals throughout the story rather than periodically dedicating specific chapters to his learned principals.
November 26, 2024
Very good book about a great Navy leader. I only wish I had the opportunity to serve with him while I was in. Adm. Winnefeld's objective was to get the mission accomplished while looking for ways to improve productivity while taking care of his sailors and soldiers.
Displaying 1 - 5 of 5 reviews