An Alum’s Creative Path

The Winsor community frequently welcomes alums back to campus, and on Friday, September 12, members of SAFA, Winsor’s fine arts club, hosted President of the Winsor Alumnae Board Meghan Weeks ’04 at the weekly all-school assembly. SAFA Heads Hannah Minn ’26 and Jiwon Lee ’27 introduced Meg to the assembled students, faculty, and staff in the David E. and Stacey L. Goel Theater.,

Stepping onto the stage, Meg admitted she was nervous. She has given plenty of lectures in her career, but never from this stage, a stage she remembers from the plays she was in during her years as a Winsor student. This time, she returned as a working artist, eager to share the winding journey that carried her from Winsor’s art studios to a plein air easel in Boston’s South End and far beyond.

Meg shared that her love of art began early. As a child, she built elaborate sandcastles, sketched endlessly, and painted the quahog shells she collected on walks. At 10, she received her first “commission”—a mural for her parents’ basement, for which they offered her what she described as the “eye-watering sum” of $100. She used the money to buy and plant a linden tree on Earth Day, a gesture that captured her belief that art could do good in the world. That same fearlessness carried her into a Nantucket gallery at age 12, where she struck a handshake deal to sell her painted shells for a net profit of $5 each. By 15, she was the youngest member of the Artists Association of Nantucket, an affiliation she still treasures.

At Winsor, Meg arrived in Class III—admitted off the waitlist just two weeks before school began. She shared she had “a bit of a chip on [her] shoulder,” feeling like a last-minute addition to the community, but committed to taking advantage of every possible opportunity she could. She found a home in the art studios, where faculty mentors like Visual Arts Department Head and Eleanor Thomas Nelson ’49 Chair in Fine Arts Sara Macaulay encouraged her to exhibit her work and build a portfolio, lessons that remain central to her practice. She also discovered passions in Latin, English, history, and physics, thanks to teachers like World Languages Faculty Sally Hatcher, History Faculty and Director of Community and Inclusion Julian Braxton, and Science Faculty and Institutional Researcher Denise Labieniec—who were all present at assembly. Meg also  immersed herself in soccer, tennis, Model U.N., theater, and tutoring. “I almost didn’t get this chance,” she told students. “So I tried everything.”

After Winsor, Meg studied architecture, drawn to the way design, history, and storytelling intersect. A graduate degree in curating followed, and she built a career in curatorial and outreach roles at the National Galleries of Scotland, the Isabella Stewart Gardner Museum, and the Boston Public Library, where she managed conservation and exhibitions in the historic McKim Building. Yet even while working in museums, she kept painting. In 2022, she took the leap to become a full-time professional artist.

Today, Meg is a plein air painter—working outside, on site, in every kind of weather. She has painted coastlines, cityscapes, and mountain ranges across the world, translating fleeting light and shifting tides into representational works that explore the structures of the built and natural environment. Her paintings have been exhibited widely, and she has earned juried membership in organizations including the Copley Society of Art, the Rockport Art Association and Museum, and the Artists Association of Nantucket. Last year, she received the Christopher A. Habilos Memorial Award for Best in Show in Any Media at the RAA&M National Exhibition.

Before concluding her talk, Meg offered a few lessons—hard-won insights she wished she had absorbed earlier in life.

• There is no perfect. Excellence matters more than flawlessness, she reminded students, and even the greats saw shortcomings in their own work.
• Creativity is everywhere. Whether on the soccer field, in physics, or in translation, creativity is problem-solving and imagination.
• Balance confidence with humility. “Be proud of your work,” she advised, “but know there is always room to grow.”
• Do good at any scale. Even a small contribution, like donating a portion of art income to causes you care about, makes a difference.

“The world needs more creatives,” Meg told students in closing. “Whatever you do, go out there and be a creative.”

Her words resonated across the David E. and Stacey L. Goel Theater: a reminder that the path from Winsor to the world is rarely straight—and that every step, every detour, can shape a meaningful life.