Purpose: The pursuit of surgical training is often hindered by systemic barriers, insufficient support structures, and the perception of an unattainable work-life balance. This study evaluates organizational support, mentorship, and well-being programs for surgical aspirants, offering insights into areas ripe for improvement to foster a more inclusive and sustainable pathway. Methodology: Utilizing a mixed-methods approach, data was gathered through surveys and qualitative comments to examine key domains: access to mentorship, perceptions of work-life balance, and institutional well-being resources. Insights were also drawn from aspirants’ lived experiences to identify gaps in existing frameworks. Results: Significant gaps were identified in mentorship allocation, with a majority finding support outside institutional structures. Well-being programs, while available, were underutilized due to perceived stigma and confidentiality concerns. Aspirants frequently cited rigid training pathways, financial burdens, and inadequate operative exposure as critical barriers. Conclusion: A paradigm shift is required to support surgical aspirants effectively. Interventions such as structured mentorship programs, enhanced flexibility in training pathways, and proactive well-being initiatives can reduce attrition and foster diversity. By addressing systemic shortcomings, institutions can empower the next generation of surgeons to thrive both personally and professionally.