Context Drawing from Ingersoll's (2001) study of teacher attrition, Huberman's (1989) study of the professional life cycle of teachers, and recent retention/attrition literature across the professions, this study seeks to make sense of the complexities of cotemporary teachers’ careers in light of changes in social and economic forces, the relationships between political and educational institutions, and the work of teaching over the past 20 years. Study Purpose and Focus The empirical part of this study explores how teachers with 4–6 years’ experience conceive of their career path in education, as well as ways that universities and schools can better partner to increase teacher job satisfaction. It also provides professional development and opportunities for growth as teacher educators, examining any potential benefits to these teachers, their schools, and the interns they work with. Participants and Setting Seven teachers with 4–6 years’ experience in one school district in the Pacific Northwest were selected as participants and mentor teachers. The main research questions were: How do teachers with 4–6 years of teaching conceive of their career path? Does taking on a teacher educator role via hosting an intern impact their long-term career plans? Throughout the 2004–2005 school year, led by the principal investigator (PI), the seven teachers participated in a variety of activities designed to support (and simultaneously study) their development as teachers and teacher educators, including workshops and seminars. Additionally, the PI created a website discussion board so that the teachers could share ideas, experiences, concerns, and questions in between the group meetings. Teachers also participated in two 45-minute individual interviews—once at the beginning, and once at the end of the school year. Research Design and Data Analysis With the retention/attrition literature inside and outside education as a framework, this was an exploratory qualitative study. Data included field notes, website and e-mail artifacts, and interview transcripts. Data analysis began with a list of initial descriptive codes, and then moved toward refining and developing new codes outside the initial list, ultimately linking codes into categories and themes. Analytical memos fostered the development of categories related to teachers’ perceived professional need for greater stimulation in the classroom and beyond. Findings Findings include that teachers with 4-6 years’ experience are searching for roles/activities that are regenerative (keeping them learning and excited about their teaching); and also generative (widening their sphere of influence, sharing their gifts with others in the profession). Further, the mentor teacher role may be uniquely suited to synergistically provide both regenerative and generative opportunities. Conclusions The paper concludes with three potential areas of exploration for both educational practice and research concerned with keeping “good teachers” teaching—merit pay, differentiated jobs, and university-school partnerships.