In 1898, 18-year-old Carlotta Stewart came to Hawai‘i with her father to continue her education and to begin planning her future; she attended Oʻahu College (Punahou) and graduated in 1902. After graduation, Carlotta received a Normal School certificate (teachers’ College,) and accepted a teaching position at the Normal School. In 1906, in addition to teaching, she was busy with classes, vacations, camping, surfing and frequent parties.
She advanced in the school system, and although many black women had established teaching careers and a handful were school administrators by 1909, it was unusual for a black woman at the age of 28 to serve as principal of a multi-racial school. She met and married Yun Tim Lai of Chinese ancestry at Anahola; he died in 1935. She never remarried and served as principal and English teacher until her retirement in 1944.