“I ended up getting involved with Planned Parenthood and volunteered at the county jail where I taught sex ED. I also volunteered with the Rape Recovery Center and worked on the crisis line. Those are the main community things I did, it changed a lot of how I ended up thinking about my career and what I wanted to do.” Guinn did not get accepted her first application cycle. After taking her post-cycle feedback to heart, she was able to really strengthen her application and in the process gain some personal insight to her own interests in the health care field. We discuss perfect timing on Guinn’s acceptance, what it’s like to create new boundaries with family when it comes to time, best practices for medical school study habits, and finally, matching with a spouse in the PhD program.