Pursuing a master's and doctorate while teaching high school presents significant challenges, primarily due to time constraints and financial limitations. The discussion highlights that PhD programs often offer funding or stipends, making them more feasible for those unable to quit their jobs. In contrast, master's programs typically require self-funding. The conversation emphasizes the need for the individual to assess their financial situation, including savings, and consider whether they can realistically balance both teaching and graduate studies. Ultimately, a decision must be made between continuing as a high school teacher or committing to further education, as managing both simultaneously is likely impractical. Additional context about the desired degree could lead to more tailored advice.