With Cristina Trifon, College & Transition Counselor

“I support the students with anything they want to do after high school.

The majority of our students transition directly into four-year college after they graduate from Oliverian, so the bulk of my work is in college counseling. For those students, I help with everything from the research process to writing essays, getting letters of recommendation, and more. Once they’re enrolled, I help them navigate things like placement tests.

And for kids who aren’t college-bound, I support them with whatever that path might look like — finding a trade school or internship program, applying for jobs, language immersions, volunteering, travel, brushing up on executive functioning skills… there are so many ways to transition out of high school!”

How do you support students throughout the year?

“The really joyful part about my job is that the senior class is very small, so I get to do a lot of one-on-one work. The seniors are all so different and have different needs.

I hold information sessions for seniors to share general information and walk them through the process. Every first quarter, during Electives Week, I offer a class called Future Planning. I try to enroll all the seniors who have upcoming deadlines so we can sit and write essays together intensively for a whole week. That really helps — we’re together for four hours every day.

I take students to two college fairs per year. All seniors go in the fall, and in the spring, I take juniors and sophomores to get their wheels turning. Typically, because of where we’re located, we attend the fairs hosted by the New England Association for College Admission Counseling. I’ll also take students to visit specific colleges of interest, as needed.”

What perspectives do you bring from your own background?

“I worked in admissions at an international college in Germany, so I was on the other side of this for a few years. That experience taught me what colleges are looking for in an application. I’ve built strong connections in the field and keep up with trends. When I attend college fairs, I network with admissions colleagues.”

What are some of the biggest challenges for students?

“Future planning can be really scary for teenagers — terrifying, even. I try to make them feel heard and understood, because there’s a comfort in that. Many students feel like they’re making a decision for the rest of their life, and that weight can make them shut down.

That’s where my time with them matters most — helping navigate that anxiety, not just for the kids but for the families, too. This process can be really hard for parents and caregivers.

One of the most challenging parts for most students is the college essay, but it’s also a space where they can really explore their inner world. Sometimes, during that exploration, students realize more of what they want in a college experience or choice. In those cases, we can pivot and adjust their list of colleges — and I’ve seen students truly find themselves through the writing process.

Sometimes, getting stuck in the process means something, and I like to explore what that might be communicating. Maybe there are other answers — or other ways of working — that are more supportive to my students.”

What happens when a student is stuck creatively?

“There are many things we can try! Sometimes, when anxiety is in the room, a student will sit in front of the computer and freeze. I try to get to know my students and figure out how to help them through those scary moments. Sometimes we hike and talk it through with the natural world. Sometimes I break the questions down and turn them into ‘journal entries’ to help take the pressure off. Sometimes we just chat — I try to be a good listener, take my time, and ask provocative questions, while my students talk and I type notes for them to return to later. Before they know it, they have an essay!”

How do you involve parents in the process?

“I get all types of feedback and involvement from parents. Some are very hands-off. Others have hired their own educational consultant. I’m flexible. My job is to support the student and the family.

A lot of what we teach at Oliverian is how to advocate for yourself — knowing what your boundaries and needs are, and learning how to make things work in a way that’s right for you.”

Final Thoughts?

“Just having someone who will really sit with you and listen — that’s so important at this stage in life. Wherever my students might land, the most important thing for me is that they feel seen and cared for during this scary time.

No one is asking you to make a permanent life decision.
Lean into what you love right now. Let that be a door you walk through.
A thousand others will open — and you get to choose which ones to explore.

And if we need to hike about it? We’ll hike about it.”