Attracting and retaining bright and motivated physicians remains a high priority for academia. Historically, the recruitment of trainees into academia and the retention of junior faculty have been suboptimal. To learn more about the perceived obstacles that discourage the pursuit of academic careers, a Workshop on Academic Career Pathways was conducted during the 2011 Southern Regional Meetings held in New Orleans. The audience included mainly residents and fellows as well as junior and senior faculties. Speakers described career options in academic medicine focusing on the clinician-investigator and the clinician-educator tracks. Afterward, the audience was asked to identify perceived obstacles to recruitment and retention in academic medicine. The group identified 10 major obstacles in 3 categories: financial challenges, personal mentoring and academic skills acquisition. This article summarizes the workshop proceedings and ends with recommendations to chairs and department leaders for improving recruitment and retention in academic medicine based on the discussion.