Alumnae and Student Share Perspectives on Life at and Beyond Winsor

Celebrating their 25th reunion, a panel of alumnae discussed how they were adapting to their lives as professionals and mothers post-Winsor, and how the confidence they gained while students had a profound impact on how they shaped their adult lives. The ongoing theme of the panel, titled Winsor’s Lasting Influence, was how they have all pushed beyond dated models and created their own that reflected the Winsor experience. 

“When I first started practicing law, I said I am a peacock feather in a sea of gray and blue suits,” said Meagan Garland ’99, a partner in the San Diego office of Duane Morris. “My goal was to bring my whole self without compromising my work. I love being a lawyer. I also love interior design. I also love travel and great food. There are lots of things I wanted to incorporate. In a big firm, I found a way to be autonomous, to combine my passions, to still do civil rights but bring in fashion and other things I like to do. Really creating that niche and space so that it is possible.”

Cecily Wardell ’99 created a nature-based independent school for children in grades Pre-K through eighth grade, echoing that theme of breaking down old models and creating new ones. “I wanted to build something that had not been built yet,” she said. “For me, being an entrepreneur is meeting a need that hasn’t yet been met.”

Kit Murray Maloney ’99 is an entrepreneur who has launched and run several feminist businesses. She discussed how she left Winsor for boarding school for two years before she returned and came back specifically for the tight-knit community. “I went to boarding school my first and second years of high school and at that school I was really struck by how my curiosity, my expectation that my voice would be heard, my assumption that if something wasn’t as equitable as I thought it should be… wasn’t held with the tenderness and the respect I’d come to assume in my first four years at Winsor. That was the core reason why I returned.”

Following the alumnae panel, a group of current students had their own panel highlighting their favorite courses at Winsor like Art and Protest, as well as how wellness and flexibility have become a staple of life at school. This has helped them to manage the competitive education and academic standards the school has, many of them said. 

“Winsor is becoming very good at recognizing mental health,” said Ainsley Wang ‘24. 

“Winsor has done a good job at recognizing that this can be a difficult place to be,” said Mia Gonzalez ’26. “I just appreciate that they are really trying.” 

“It’s not easy to be at Winsor,” said Gwen Castro ‘24. “I [also] don’t think it should be. The resources have changed to deal with the workload. We have so many resources now.” 

In a moment of levity, when the students were asked what alumnae might be surprised to learn about today’s campus, Alessa Andrews ’26 replied: “The amount of Starbucks this school consumes.” 

Moving from a panel of innovative and successful alumnae discussing their careers and lives outside of work into a current student roundtable, you could not help but be struck that both groups echoed one another, specifically when they were asked to give advice to their younger selves. 

“Be softer with yourself, without losing ambition,” said Kit. 

Gwen said she spent a lot of her Upper School career stressed. “I wish I knew to savor all the moments.”