I told him about the trip I was planning and explained that I would be resigning near the end of March. He was surprisingly understanding and seemed excited for me when I explained my trip to him. Any worries that I may have had about resigning had subsided. It was done.
Since then, I have purchased my one way plane ticket to Colombia! I have added more cities and countries to my itinerary, and plan to travel for at least the next six months. I am extremely excited! The future is here, and it looks bright!