An interview with Chloe Loeffelholz, Development Manager
Maggie O’Brien (she/they) is a TTS21, Spring 2013 Traveling School alum. Today, Maggie is a queer writer, artist, educator, and college essay counselor, helping the next generation follow uncommon paths for the common good. Read more about The Traveling School’s impact on Maggie and how TTS uniquely prepares students for the college admissions process.
What’re you up to now more than a decade after your semester in Central America?
For the past five years—after graduating from Colorado College with a self-designed degree in Creative Writing for Social Change—I’ve found myself wearing many hats: I’ve worked for a college access non-profit, I’ve led backpacking and climbing trips for LGBTQ youth with Women’s Wilderness, I’ve done copywriting for museums, and for the past two years I taught Ceramics at an arts-focused boarding school in the Berkshires, while also working as a writing coach for College Essay Guy. In the mix of all of that, I was diagnosed with chronic lyme disease and found myself on an incredibly challenging yet transforming healing journey. As I regained my health, I felt a calling to finally create something that aligned with my values and interests—a company that helped diverse, creative, adventurous, and passionate young people authentically follow their own path and tell their own stories. I then founded Uncommon College Counseling, and I now get to work with incredible high school students—TTS alum of course being my favorite—through the college application process. Beyond my career, I’m also writing a book of personal essays, and find time every day to go swimming in cold water, hike, drink tea, go to yoga class, pull tarot cards, buy flowers at the farmers market, and read as many books as I can get my hands on.
How did your Traveling School semester impact you?
I come from a lineage of farmers, utopia dreamers, artists, lawyers, teachers, and small business owners, but at sixteen, I found myself swamped in a life of suburbia—I was a good student and a good athlete, a white, closeted American teenager who’s perception of the world only stretched the five miles between my town lines.
In my mind, there’s my life before The Traveling School—and there’s my life after. It was the same feeling I have when I emerge from water: You go from normality to a state of sudden awakeness, cells buzzing, like a deep breath, everything brighter and more distinct around you. That was TTS for me. I became enraged by the culpability of the United States and neo-colonization of Latin America, the civil wars we started, the food systems we corrupted—and I became amazed by the indigenous futurism underfoot, the seeds being saved, and the rebels who organized. I came home radically altered, unable to go back to who I was before.
When I trace the lines of The Traveling School in life, they show up most distinctly in my orientation towards justice and critical lens of the world. If it were not for TTS, I wouldn’t have moved to Kathmandu, Nepal by myself after graduating from high school, I wouldn’t have gone to a college that valued experiential education, I wouldn’t have designed my own major immersing myself in critical race studies, immigration, queer and feminist theory, environmentalism, and education, and I wouldn’t have this seering belief I have today that there are more ways to walk on this earth than the western, corporate, supremacist world tells us there are.
Is there a specific lesson from your semester that sticks with you today?
In the highlands of Chiapas, Mexico, I became entranced by the poetic revolutionaries known as the Zapatistas. We met with several members during my semester, and I remember sitting on the floor of a small room in San Cristobal, listening to lyrical Spanish words that described an indigenous uprising rooted in gender equality, political autonomy, and a complete restructuring of power. The Zapatistas created their own community, separate from the Mexican government, known as the caracoles—a snail’s shell. In many cultures, this spiral shape represents the interweaving of the past, present, and future of the universe.
What I found most compelling about the Zapatistas—so much so that I went on to write a thesis on them later in high school—is how they resisted an oppressive system, while still technically residing within its borders. This is something I’m often thinking about: For many reasons, a countless number of our societal structures are no longer working. I want to know what it looks like to empower a new generation to follow uncommon paths for the common good, building a future based on mutual care for each other and the planet. As the Zapatistas say: “Un otro mundo es posible.” Another world is possible.
How does The Traveling School prepare its alumni for the college admissions process?
The landscape of college admissions is in constant flux. It’s shaped by policy, technology, institutional priorities, national trends, and demand —with topics like AI, the end of affirmative action, increasing selectivity, standardized testing, and free speech taking center stage. As application numbers increase—and landing a seat at a selective school becomes paralyzingly more challenging—students find themselves bracing against an “achievement culture” of perfectionism, excellence, and pressure.
The Traveling School is an antidote. Rather than fit the mold, stay glued to a screen, and do what’s expected of them—TTS students break expectations. College Admissions offices want applicants who take initiative, seek challenges, engage their curiosity, contribute to their communities, and gain a broader perspective of the world. Although it’s helpful to have experiences like this on your resume, I truthfully believe it’s more than that: By going off the beaten path, Traveling School students learn the value of a meaningful, immersive education, and walk away with a level of self-awareness that will infuse the rest of their academic journey. Instead of joining a school club for the sake of it—they’ll start one because they believe in it. Instead of taking an easier class to get a good grade—they’ll choose a harder class to learn something they’re genuinely interested in.
I believe the college application process should be an opportunity to reflect, envision your future, and find purpose, rather than being something that determines a student’s self-worth based on acceptance or rejection. For any Traveling School student, they’re already two steps ahead. Students return from their semester not only with a story to tell, but with a more authentic internal compass that helps them go where they want to go, rather than where society tells them they should.
Interested in exploring more alumni stories? Check out The Traveling School’s 2023 Impact Report.