"It wasn't just me trying to be a doctor, my whole family, my wife and my kids, they just loved the idea and were supportive and kind." Kyle started medical school at 34 with full support from his wife and kids. It wasn’t until his psychiatry rotation that he realized where he wanted to be. With a background in social work, Kyle came to understand that the experiences from his past were an important part of his future. We discuss how that journey transpired, what makes medical school a different challenge than regular university, and finally how it feels to first anticipate your match results, then work through the emotions of finding out where you will spend the next several years of your life.