The study examines factors that boost principals’ sense of resilience in their first year, as well as those that undermine it. 61 interviews were conducted with 21 school principals from five different districts throughout their first year in the role. Analysis revealed five categories of resilience-undermining factors. (1) Work overload that creates a sense of stress; (2) Difficulties in dealing with key players; (3) Lack of administrative knowledge; (4) Acceptance or rejection by the staff; and (5) Coping with the Covid-19 crisis. The analysis also revealed five categories of resilience-boosting factors: (1) Growth resulting from biographical events; (2) Short-term successes; (3) Supportive environment; (4) Drawing strength from the student environment; and (5) Acceptance by the staff. This study proposes ways of coping with the challenges of principalship through the prism of the resilience determinants of principals when entering their role.