How does a traditionally educated New York City career woman who once obsessed about getting her kids into the right preschool end up living off the grid in Africa and unschooling her two children ? Find out in this collection of essays based on the author's personal journey of moving away from the status quo and creating a life of choice and autonomy. Part memoir, part journalistic enquiry, Rowland explores topics ranging from how her children learned to read and write without formal instruction and what it means to trust children to build their own education, to why we should all walk barefoot and what happens when we try to flip an omelet and fail--all from the perspective of challenging societal "shoulds." As the debate continues on how to improve our failed education system, the author delves into what it's like to live, learn, and parent without it. Filled with optimism, humor, and candid reflection, this book is ultimately a memoir about questioning everything we think we know and taking the risk to find our own answers.