A soulful guide to embracing uncertainty, unlearning what no longer serves us, and discovering the beauty of becoming through life's transitions. It's Good to Be Lost Once in a While seeks to help us, at different times in our day and life, to respond to the overarching question: What can I do most beautifully with my life? The book, as a whole, reminds us that as we move through the day and different phases of our life, as well as are required to face both inner transitions and external change, we must recognize that we are simultaneously the expert and the novice. Being concerned about the impact of what we don't already know is natural. However, an even greater danger to living a rich and meaningful life is what we think we already know, but really don't. When we are willing to humbly honor this reality, we are more able to let go, unlearn, and embrace needed additional knowledge when necessary. In the process, we can better discern our true gifts and welcome the heretofore unimaginable faces of...new possibility. To enable this process to become richer, the following themes are explored: discernment, knowing the 5 necessary companions we need for our life's journey to be meaningful and satisfying, overcoming psychological resistance to growth and change, enhancing kenosis (inner spaciousness), mindfulness and the reflective process, mining the positive results of failure and uncertainty, and applying the principles of posttraumatic growth (PTG) in the search for possibility.