Anna Cipollone '17

When Anna Cipollone ‘17 graduated from Georgetown University with a degree in English and art history, she saw several professional paths fall before her - she enjoyed editing, having worked as a technical writer and editor for a government military contractor, and had considered teaching. 

“In conversations I had with Mary Ortiz when I came back as an alumna to visit Oakcrest, I knew that if I was going to teach, I was going to do it here,” she said. “I was confident in the skills and the preparations that Oakcrest had given me in high school and to be part of this education is a gift.”

Some Oakcrest traditions Ms. Cipollone is glad to see continue are the monthly all-school ComHoms and Spirit Week. As a senior at Oakcrest, Ms. Cipollone had served on student council as vice president, so she said she remembers all the work that went into the events that pays off with all the fun. 

While studying at Georgetown, Ms. Cipollone participated in the Villa Le Balze program in Florence, Italy where she took classes in Italian 20th century literature and art history.

“Being in Florence, the birthplace of the Renaissance, was a very immersive experience,” she said. “I got to travel around Europe, both in and outside Italy.” 

One aspect of her Oakcrest education that Ms. Cipollone believes set her apart from her peers at the university was her writing skills that were formed at Oakcrest. 

“The difference between my writing and skills I had developed in high school compared with my peers was vast,” she said. “I felt so much more prepared and able to effectively organize my thoughts and write with clarity - something that was important for me to teach now as well, especially as an English teacher.” 

Ms. Cipollone teaches sixth and seventh grade English, along with ninth grade logic and rhetoric. She said she enjoys being able to teach the younger Oakcrest students and help form them in their love for English just as she had been as an Oakcrest student. 

However, Ms. Cipollone also says that the students are teaching her. 

“Sixth and seventh graders are seeing books on a different level than I am used to,” she said. “It is interesting to see what sticks with them as we read. Their sense of wonder and excitement has been an encouragement. Especially the sixth graders have this sense of positivity and willingness to try things, even if they’re intimidated, which is really encouraging to see.”