Starting out young and inexperienced, but with entrepreneurial inclinations and a desire to create opportunities for others who were less fortunate to improve their lives, Jim McClelland led Goodwill Industries in central Indiana for 41 years. During those four decades, the Indianapolis-based organization grew and evolved into a large, diversified social enterprise that employed over 3,000 people, two-thirds of them with barriers such as a significant disability, felony record, or lack of a high school diploma. In addition, Goodwill operated 12 public charter high schools designed for adults who lacked a diploma, offered a nurse home visitation program for first-time moms in low income households, and linked employment, education, health, and other services in a whole-person, often whole-family approach for greater lasting impact. As he approached retirement in 2015, Jim identified 104 significant initiatives the organization had undertaken during his career, and he classified them in baseball terms. There were 10 home runs – eight with bases loaded, 18 strikeouts, a lot of singles, and a few doubles. But the impact of those eight grand slam home runs far exceeded the net cumulative impact of all the other initiatives. In this book Jim describes much of what worked, some of the initiatives that didn't, and leadership lessons he learned as both he and the organization grew. He also describes how the organization adapted to dramatic changes in the economy, demographics, technology, competition, laws and regulations, and to some geopolitical shocks during his career. Material in this book will be of particular interest to leaders and aspiring leaders of for-profit and not-for-profit social enterprises, and much of it is applicable in other businesses as well.