The researcher assessed the subject teachers’ levels of satisfaction and/or dissatisfaction using the Herzberg Two-Factor Theory. The study assesses employee motivation and hygiene, as discussed in the first part of the study about exploring the socio-demographic profile and job satisfaction level among teachers in Alaska. Frederick Herzberg (1923–2000) was a well-known author, and his work was praised by the Harvard Business Review. His theory has been widely accepted by many different groups and studies, with many people adapting and applying the theory to business management. For many years, teachers have been leaving school districts, particularly in Alaska, and this project seeks to investigate the causes of this phenomenon. Running a school is like running a business, except your clients or customers are students and parents. You must be able to choose what type of education they require. Schools have a system structure that is like a business. A school district that oversees several schools is analogous to a conglomerate that oversees a group of businesses. The study was conducted in the Bering Strait School District, in northwest Alaska, which serves fifteen isolated villages and two islands. Various methods including survey questionnaires, interviews and data gathering, were used and implemented. Out of 30 targeted respondents, 13 had high hygiene and high motivator factor (HHHM) scores and were further analyzed through interviews, with the data gathered subjected to thematic analysis. It was noted that some of the factors that affected the respondents in leaving their school are professional-related reasons, professional growth, job stability, physiological growth, no consistent reliable childcare options or childcare, very cold weather, and emotional reasons. Lack of these factors can influence the participants to seek such services elsewhere—from another workplace that can provide them with these services, and thus give them comfort, and peace of mind as well.