Individuals who change careers to assume teaching roles in secondary schools are more likely to struggle in the classroom than those without such backgrounds. In this investigation, we identified three such career-changing teachers who were beginning their education careers in rural schools, and observed and interviewed them throughout their first year of teaching to understand their unique challenges and to identify the types of supports that they found to be most helpful. Three primary themes emerged: (1) adjustment to the unique culture of a school, (2) the importance of mentoring, and (3) adaptation of previous work experiences to teaching. Recommendations included more emphasis in teacher preparation programs of awareness of the uniqueness of every school's particular culture and the critical nature of effective mentoring in the success and happiness of these career-changing teachers.