Background The magnitude of student debt plaguing our nation is a major topic in political and academic spheres with median medical student debt of $200,000. This is compounded by poor financial health during training. This study evaluates how debt and financial wellness influence resident perceived stress, mental health, career plans, and relationships. Methods General surgery trainees at an academic institution were surveyed regarding financial parameters, perceived stress, and the impact of finances on their career and family life. A validated stress assessment instrument, the Perceived Stress Scale, was used to evaluate trainee stress. The median perceived stress score was compared for groups using a Wilcoxon rank-sum test. Results Fifty-eight (61% response rate) residents responded to the survey. The median (range) student loan debt was $200,000-500,000 ($0-750,000) and savings was $5000-10,000 ($0-20,000+). 18 (31%) trainees had monthly credit card debt. Half of the respondents did not have enough liquid assets for an emergency fund, defined as 3 mo of living expenses. The median perceived stress score was 16 (1-30) or moderate stress. Perceived stress score was significantly associated with the trainee’s response to how finances impacted their future career choice, practice style, and relationships (P< 0.005 for all). However, the perceived stress score was not associated with objective measures of financial wellness, such as the overall level of medical school debt, savings, or having an emergency fund. Discussion The trainee’s subjective perception of financial wellness, rather than objective financial parameters was associated with higher levels of perceived stress, the strain on relationships, and a greater impact on future practice styles. The majority of surgery residents did not have enough liquid assets for an emergency fund, independent of the level of debt, which emphasizes how financially leveraged residents are during training. Although burnout during surgical training is multifactorial, formal financial education incorporated into graduate medical education programs could increase financial literacy, help to mitigate financial risk, and ultimately decrease some of the perceived stress residents possess.