As the field of medicine changes to align with technological advancements, government regulations, and insurance reimbursement, dermatology residents are faced with the increasingly difficult task of selecting the practice model that best fits their personal and professional goals. Private practice can provide greater autonomy and higher earning potential but requires strong business acumen and carries major financial risks. Academic dermatology prioritizes teaching, research, and collaboration but often generates less compensation and has increased institutional responsibilities. Hybrid models, Veterans Affairs (VA) positions, and rural practice present additional options with varying degrees of flexibility and support. Although career decisions may seem overwhelming, dermatology residents can choose the right path and achieve a fulfilling career by educating themselves about practice models, clearly assessing personal goals, and identifying supportive mentors.