A typical day for Caleb Gessmann might include flying to South Florida to have lunch with his family and friends, going out on a fishing boat with his soon-to-be brother-in-law and then flying back to school at Embry-Riddle Aeronautical University to take some exams. Then, in the same week, he could be flying on a contract flight to the Bahamas. Being 20 years old and living this lifestyle is achievable. Let Gessmann tell you how.