Summary of Rethinking Success

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Rethinking Success book summary

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  • Applicable
  • Concrete Examples
  • Engaging


Author J. Douglas Holladay explores people’s contradictory reactions to success: Many people gain what they think they want and yet remain unfulfilled. All too often, business advancement and wealth bring unhappiness rather than contentment and joy. The author takes a wise, compassionate look at why this occurs and how you can embrace the good and bad in your life. Holladay details eight practices which can help you lead a meaningful life. His insights and guidance will appeal to those who like to reflect on challenging life issues or who cannot understand why success doesn’t feel a little better.

About the Author

Ambassador J. Douglas Holladay has had a varied career having served in the Department of State, the White House and Goldman, Sachs. He continues to be an active investor while both teaching in the Georgetown University business school and running Pathnorth, an initiative for CEOs and business owners in search of greater meaning in their lives.


Success can leave people feeling rudderless unless they have a clear direction. Follow eight practices to add meaning to your life.

Many successful people suffer an unexpected affliction: discontent. For example, consider Markus Persson, creator of the video game, Minecraft. In 2014, at age 35, he sold his company, Mojang, to Microsoft. He earned $2.5 billion from the sale. However, after it went through, he didn’t live in a state of bliss fueled by his new-found wealth. His Twitter feed suggested that he suffered depression and loneliness.

Many people suffer similarly. Despite their success, they feel despondent. They can’t seem to find a way to live a fulfilling life. People who lack a clear plan for the future can find that success leaves them feeling unmoored. Scholars suggest that to live a life with meaning, people must fulfill three preconditions. First, they must have a purpose which gives them a sense of direction and which helps the world make sense to them. Second, they must feel they are a part of something larger than themselves. Third, they must maintain connections...

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