In a post-COVID world where status quo changes every second, transitions are bound to catch us off guard every now and then. Whether or not the transitions are welcomed one needs to navigate their careers in a way that answer two key questions - where to play and how to win. In order to do so, a transitions coach often helps people reflect on where to go and how to grow. In light of this context, Deepak Jayaraman, in conversation with author Abhijit Bhaduri, offers significant insights about how to navigate careers in a manner where people can realize their own potential.