What Would You Do If You Weren't Afraid?: Discover a Life Filled with Purpose and Joy Through the Secrets of Jewish Wisdom by Michal Oshman is a fine book, and if you don’t have a wide Jewish background, this book is a great start.
I have two issues that are a problem for me, but probably not others. I don’t believe that we have something like a stable, unchanging soul. The author does and it is key to her thesis. I also do not believe that we have a singular destiny. Maybe we have more than one?
I also have a prejudicial attitude about people who coach executives and work on corporate culture. But that is my problem. Additionally, I am not sure how "secret" this Jewish wisdom actually is...