In many fields, the percentage of professionals having one or more jobs in addition to their full-time primary job is increasing worldwide. With numerous members earning relatively modest salaries, teachers are a professional group among the most affected by this tendency. Traditionally, "moonlighting" (the commonly used term for having an additional job) is considered to be highly problematic in terms of a teacher's ability to fulfil their teaching responsibilities. However, little attention has been paid to the potential that "teacher-moonlighters" could have in contributing to school life by using their out-of-school work experience. This article introduces a small-scale narrative study with teachers from Estonia and proposes a preliminary typology of teachers having multiple jobs. Providing examples from narrative life history interviews, it is argued that certain types of teachers have the potential to enrich school life. Two dimensions appeared to be most indicative for categorizing teachers with multiple jobs: "permanence" and "self-actualization through multiple jobs." The researchers argue that these dimensions are promising for further discussion of teacher career patterns in which multiple jobs can be seen not as obstructive, but as contributing to teachers' professionalism.