Wow, that's a lot to answer. Actually, I kind of just arrived there. I coached basketball for many years while teaching mathematics. I acquired my M.Ed in School Administration and served as an assistant principal for 5 years before ending my career as an athletic director. I held that title for 4 years at Martha's Vineyard Regional High School. Honestly, it was my favorite 4 years of my career. I loved it. You definitely need excellent organizational skills, the ability to multitask, and time management skills. Most of all, you need to love what you are doing. I hope this helps and I encourage you to follow your heart and your dreams.