[1][2][3] She studied painting at the University of Wisconsin–Madison, where she became part of a group of magical realist painters, including Gertrude Abercrombie, Marshall Glasier, John Wilde, Dudley Huppler, and Karl Priebe.

"[6] Beginning in the 1940s, Fein lived for a time in Mexico, then in the San Francisco Bay Area of California, eventually settling in the town of Martinez.

[3] During her youth, Fein described herself as being a quiet child, and stated in an interview that while in school, "I was always considered dumb.

[3] Though initially wanting to enroll in the Art program, Fein would later recall her sister saying to her, "Yes, but you'd never get a job when you got out of college, so you should enter the home ec[onomics] school and at least then you could become a teacher.

While completing her program, she was introduced to John Wilde, Gertrude Abercrombie, Marshall Glasier, Dudley Huppler, and Karl Priebe, all of whom would later be referred to as the "surrealists of the Midwest."

She planned to visit her mother in Mexico City, but Fein was convinced by a classmate to travel to Ajijic on the shores of Lake Chapala, where she lived and painted for three years.

Along with painting, Fein helped rebuild the adobe house in which she had her studio, taught English to young people, and started an embroidered blouse industry for women.

In the 1946-47 Whitney Annual exhibition, Fein's work was shown alongside that of Max Ernst, Roberto Matta, and Jackson Pollock.

[9] Her second book, First Drawings: Genesis of Visual Thinking, is about the basic patterns that appear throughout human art, both historically and during childhood development.

[10] Fein's hope with First Drawings was to showcase the relationship between the art done by children and the cave paintings of the Paleolithic period.