The road to finding a career path as a Trade and Industrial (T&I) or Healthcare Science (HSTE) (formerly Heath Occupations) teacher is winding at best. Job incumbents in this profession are hired after years of employment in an occupational field, and subsequently obtain the necessary credentials for their new teaching career. Various models of career motivation offer reasons why individuals choose a certain career and reasons why individuals may or may not be successful in a career choice. Additionally, a variety of theories have been offered to explain career choices of people in general, for those in helping careers and for those in career and technical education. While these models and theories have great value to any discussion on career development, they fall short when it comes to determining why individuals whose first career choice was to work in a trade or in healthcare make a career change into teaching, and what influences them to make that change. In fact, the career development of T&I and HSTE teachers is largely unknown and overlooked. This exploratory study surfaced from the researchers' experience as T&I and HSTE teacher educators, and a review of previous research and literature revealing a scarcity of available data about the reasons T&I and HSTE professionals choose to change careers and become teachers. The authors' primary purpose is to describe the career choice motivations of T&I and HSTE teachers. From a practical standpoint, they would like to provide insight for those in the school system who recruit teachers and those who have the goal to retain them. It is their belief that one must understand the career motivations of new T&I and HSTE teachers in order to provide better induction into the field, mentoring that matches needs and stronger retention.