In 1886 she followed her family on a -sixteen month- trip to Europe. This voyage gave her the opportunity to expand her knowledge of the classics. While studying languages on the trip, she met an instructor from Vassar named Abby Leach. This woman was the person who gave her the idea to pursue a teaching career. Right after her return to Massachusetts and with the intervention of her father, she got an interview with the President of Wellesley College, an arts college for women, which was located close to her home. In the fall of 1887 she began tutoring students in Greek.
During her stay at Wellesley, her interest in philosophy was noticed, and she was offered a position in the experimental psychology department of the college, even thought she didn't have any training in this field. Because of her gender, petitions were made to get her hired and with the condition to keep the job for one year. Also she was required to study for a year in a Psychology program. Once again the fact that she was a woman made necessary some special arrangements for being able to attend seminars as a "guest" at Harvard, under William James and Josiah Royce. Although, the university administration made clear that Calkins was restricted of registration as a student.