Noting the increasing need for Head Start's efforts to support parents' personal and professional success, this guide for Head Start staff examines the success process at both the individual and the program level, and explores strategies that strengthen the larger community's support for families as they define and build upon success. Following an introductory section, the guide presents three training modules. Each module details expected outcomes, key concepts, background information, learning activities, and next steps. Handouts are included for each module. Module One, "Focusing on Success," provides skill-building in such areas as defining success for oneself, setting priorities, and moving toward goals. Module Two, "Working the Head Start Success Ladder," guides participants in an examination of what Head Start can do to assist individuals as they establish and pursue goals, in particular goals related to economic well-being. Module Three, "Building Success in the Community," expands the focus to the world beyond Head Start by examining the role Head Start plays in fostering a community where all members can achieve their personal visions of success. The final sections of the guide contain information on continuing professional development, and publication and organization resources. Three appendices describe Project Match and Economic Independence; a community framework for Head Start; and elements of federal welfare reform. (SD)