New but Familiar Beginnings for Ms. O’Connor

With her passion for literature and coaching, Ms. O’Connor joins Middlesex eager to build strong relationships.

Image by: Lucy Wang '27

Over the years, Middlesex has welcomed new faculty and students who continued to enrich its community and culture. With multiple new faculty members for the 2025 to 2026 school year, I had the opportunity to sit down with Ms. O’Connor, a new English teacher, to learn more about her journey and what brought her to Middlesex. 

Ms. O’Connor is from New Canaan Conneticutt, and attended boarding school at Deerfield Academy. She went on to Williams College, where she majored in American Studies and received her degree in Education. With the combination of Deerfield's high academic challenges and Williams’ close-knit community, Ms. O'Connor found a love for English and teaching. She explored her love for writing throughout her time at Williams while engaging in thoughtful and intellectual conversations at any chance she could. Ms. Connor previously taught at Lawrenceville School in New Jersey, another prestigious boarding school in our area. This will be her third year teaching. 

Why Middlesex? As someone who grew up around boarding schools, Ms. O’Connor wanted to continue her career influencing young boys and girls who were just like her. Boarding schools had everything she was looking for. Ms. O’Connor was the captain of cross country and track while at Williams College, later continuing her passion as a coach at Lawrenceville. Now at Middlesex, she is excited to combine her love for both teaching and coaching.

In addition, Ms. O’Connor was drawn to Middlesex’s English department. “The English Department has a really great mission of making every student into a really strong writer,” she explains. Middlesex’s Writing Workshop, required for all students, aligns perfectly with her educational philosophy. Ms. O’Connor believes that “[Middlesex] really believe[s] that everyone can be a great writer.” She is excited to sit into various workshops and understand the basic fundamentals of writing that Middlesex teaches their students. Primarily teaching upperclassmen, she is thrilled to engage in interesting and complex conversations with her students. 

While she was working on her education degree at Lawrenceville, Ms. O’Connor focused on creating a supportive classroom environment where kids learn to build off each other and help each other through discussion. She wanted to make sure everyone felt comfortable with participating and speaking directly to her. “I come to teaching with a relationship focus, caring about the dynamics between the students and the class and also between me and the students,” she states. Middlesex is excited to see what Ms. O’Connor has to offer in the classroom.

As a new faculty member, Ms. O’Connor has been amazed by the tight-knit community at Middlesex. In her first couple weeks, she enjoyed the opportunity of being a dorm parent. She says, “I’m doing duty in BP and I've been really loving getting to know the other adults who live there and also the students.” And with the addition of the campus being beautiful to the eye, Ms. O’Connor expresses her gratitude for the welcoming environment and “how warm people seem.” 

Ms. O’Connor is excited to see what this journey ahead of her holds. She plans on learning from the returning faculty and creating a home here. “I hope I'm here for a long time. I think it's a really sweet community and Concord seems like a good town.” With all of her ambition and open-mindedness, we welcome Ms. O’Connor with open arms to the community. Middlesex cannot wait to see how her story unfolds!

Sayde Brown ‘27