Josephine is a born and bred Staten Islander. She began her education at St. John Villa Academy, graduating from high school two years earlier than her classmates did. She then moved on to the City College of New York where she received a Bachelor of Science in Mathematics, one of the very few women in her class.
Soon after she received a Master's of Science in Mathematics, also from the City College of New York, and began to teach math at her Alma Mater, St. John Villa Academy, for 13 years, during which time she was the chair of the math department for five years. Desiring a career change after all of her accomplishments in the field of mathematics, Josephine ventured into the world of insurance.