Kauwila was raised in two rural Hawaiian communities: Moloka‘i and Kaupo, (Hana), Maui. She is the middle child in a large family that relied heavily upon the land and sea to provide for their needs. She has a BEd and teaching certificate from UH Manoa and has worked with youth in various capacities both in and out of the classroom, including many years with youth at the Molokai Youth Center and at other Molokai programs. In addition, she has worked in various Hawaiian charter schools and with the Hawaiian Language Newspaper Indexing Project. Kauwila has been a student of the Hawaiian culture for most of her life and has a deep love for Hawaii. This aloha guides the work she does in her home communities with kupuna and with youth.