The Uncommon Team
Maggie O’Brien | She/They
Founder
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Maggie O’Brien is a queer writer, artist, and educator who grew up outside of Boston and now lives in the Berkshires. She founded Uncommon to reimagine college and career planning, and to encourage people to think deeply, tell their stories, and follow unconventional paths.
Maggie has coached dozens of students through the college application process on their way to some of the country’s top schools, and has worked for the Admissions Office of a selective liberal arts school, a college access non-profit, and College Essay Guy. Maggie also has a decade of experience working in the outdoor industry as a guide, program developer, and risk management advisor for organizations like Overland Summers and Women’s Wilderness, and deeply values experiential education and real-world immersion. In all her work, Maggie supports her students through genuine connection and a keen understanding of diversity and belonging.
Maggie has her B.A. from Colorado College in Creative Writing for Social Change, attended the Traveling School semester program in high school, and went on a gap year in Nepal before starting college. Her writing has been recognized by nationally acclaimed publications, and her creative work has brought her to public radio production, museum design, story slamming, ceramics, and more. You’ll usually find her hiking in New England forests, doing yoga, watching live music, and making her own teas.
Wayan Buschman | She/Her
College Counselor
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Wayan Buschman (pronounced “why-ON”) is an artist, writer, tutor, and educator, with a background working in the Semester School Network. She was born and raised in New York City, which is also where she lives currently.
Wayan’s background in one-on-one mentorship started during her undergraduate years at Colorado College. While Wayan studied for her BA in English literature, she worked as a writing consultant at the Ruth Barton Writing Center, where she helped to brainstorm and workshop papers with students across all disciplines.
After graduation, she worked at the High Mountain Institute in Leadville, CO as the English Apprentice. She then made the leap to Napa, California, where she served as the Humanities Teacher at the Oxbow School for Art and Academics. Outside of formal classes at Oxbow, Wayan arranged exploratory college prep electives, college essay writing workshops, and art portfolio critiques. Wayan still teaches and tutors in the virtual sphere and, when she’s not working, you can find her playing off-key banjo tunes, drawing comics, and reading short stories.
Alex Tomb | She/Her
Gap Year Counselor
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Alex Tomb is an accomplished wilderness educator, world traveler, and wildlife ecologist who grew up in both Southern California and Connecticut. For now, she’s made her home in the forests of Northern California.
With nearly a decade of international travel experience spanning 26 countries and four continents, Alex brings firsthand expertise in helping young folks design transformative and culturally immersive adventures that help them discover their authentic path forward. From conducting wildlife research in Madagascar to building homes in rural Cambodia, Alex's personal gap year experiences inform her uniquely qualified perspective on crafting life-changing gap year journeys.
Alex has spent the last three years as Head of Wilderness Leadership Expeditions at Camp Onaway, designing and leading month-long backcountry expeditions for teens. This role, combined with her position as director of the Trips Department and her work developing nature-immersion programs at White Pine Programs, has honed her ability to mentor young people through challenging transitions and growth experiences.
Alex graduated summa cum laude from Skidmore College with a B.A. in Integrative Biology, and is an alumna of the High Mountain Institute semester program. Whether she's teaching conservation in rural villages, goat-herding in the mountains of Slovenia, or walking alongside an indigenous hunter-gatherer tribe, Alex intimately understands the transformative power of saying yes to the adventure of a lifetime.
Madison Newbound | She/Her
College Essay Counselor
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Madison Newbound is a writer who recently relocated to the Berkshires from New York City. After years working as an editorial assistant at Penguin Random House and ICM partners (now CAA), she quit book publishing to work in restaurants and pursue her own writing. In 2024, she published her debut novel, Misrecognition, with Simon & Schuster in the U.S., and Bloomsbury in the U.K, and is currently at work on her second book.
Madison graduated magna cum laude from Tufts University, with a B.A. in International Literary and Visual Studies. She spent her senior year at Tufts in Paris, where she lived with a host family and completed coursework at the Sorbonne. Over the summers in college, she worked for the Tufts European Center in Talloires, France, where she led hikes, organized educational excursions, and helped facilitate academic programming for both high school and college students. Before learning French in college, Madison attended School Year Abroad in Zaragoza, Spain.
When she is not reading or writing, Madison is at the local sauna, taking a walk in nature, or beading necklaces for friends and loved ones.