“I had to ask myself some serious questions. One of them was: If you get to the end of your life and this is what you did, you stayed in real estate, would you feel like you had done enough? The answer for me was no, so I knew I had to make a change.” In the back of her mind, Jessica had always wanted to be a doctor. As a single mother of three, she prioritized taking care of her family by building a successful career in real estate. Jessica remarried, and with the support of her family, the dream of going into medicine became a reality. We discuss the process of making a serious career change, balancing family life with medical school, the benefit of being a non-traditional student with life experience, personal growth as a couple through mutual sacrifice, choosing a specialty, and finally, preparing to apply for residency.