The main purpose of the present study was to illuminate the factors that enhance or inhibit job satisfaction among second-career teachers (SCTs) in their initial period at school. Data was gathered from questionnaires filled out by 80 novice SCTs and a comparable group of 82 First-Career Teachers (FCTs). Personal interviews were conducted with eight SCTs. The findings show that the most powerful predictor of high job satisfaction among SCTs is the availability of support whereas the most powerful predictor among FCTs is workload. The qualitative analysis suggests that experience acquired by SCTs before they start teaching provides a repertoire of helpful strategies, thus improving their ability to cope with stressful experiences. The findings support the trend to advocate teaching as a second career for experienced professionals.