About this Service

Uncommon Futures is a boutique college and gap year counseling company whose mission is to empower a new generation to follow uncommon paths for the common good. Whether you're a high school student ready to explore, a college student seeking clarity and purpose, or someone mid-career looking for a meaningful shift, we'd love to work with you!

We guide students 1-on-1 through every step of the college application process, from brainstorming, to creating a college list, writing essays, managing acceptances, and learning insights into college admissions. We offer both a college counseling package and college essay coaching package for students in 9-12th grade.

We also work with anyone searching for a gap experience--whether that's a summer, semester, or year. Through 1-on-1 meetings, we’ll help you reflect, plan, and embark on your gap experience. This includes helping you find and apply to opportunities, draft a budget, make a custom itinerary, get travel insurance, defer from college, receive college credit, create packing lists, and feel supported throughout your entire journey.

Our spots for 2025 are starting to fill up, so if you're interested in working with us, reach out sooner rather than later. We offer free consultations, and would love to chat with you!

About this Lister

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 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.

Background and Expertise

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 support her students through genuine connection and a keen understanding of diversity and belonging.