Our current reality is informed by where we have been historically and the vanguard of theorists who influenced today’s perspectives. Who are workers and what are they facing today? What is the historical foundation for today’s reality? Is it as dismal as some of the statistics suggest? How do organizations embrace the whole person at work and how do they bring work to life? How do leaders create the context for joy? This chapter describes our current conundrum of work and life with these questions in mind.