“Good morning! It’s Work Your Package Wednesday. I am Ayanna Castro, Founder and Chief Maven of Work Your Package”: The greeting that welcomed thousands of viewers of Ayanna’s weekly live video posts for two years. Filled with anecdotal, transparent and thought-provoking commentaries, the posts sparked conversation, reflection, and action. Rarely scripted, Ayanna speaks from her heart, experiences, and observations to provide life-witness wisdom and humor on a variety of topics. This book is written as a one-on-one conversation with accompanying thought-provoking questions and exercises and designed to encourage the reader to be introspective and proactive in creating the life they deserve.