Sydney Montgomery ’15 Helps First-Gen Students Apply to College

When Sydney Montgomery ’15 was growing up in Montgomery County, Maryland, she recalls looking over her SAT score and thinking, “That’s a great score. I think.” Her score was 1520 out of 1600.

But when she overheard classmates remarking on their scores, she realized hers wasn’t all that impressive. She says, “I remember being disappointed thinking this score wasn’t good enough to get into Princeton. I thought I should’ve tried harder.”

But her SAT score and application were strong enough for Princeton to accept her, and she earned a degree in English. She later graduated from Harvard Law School.

Montgomery’s experience applying for post-secondary schools inspired her to train her sights on her entrepreneurial dream: consulting with college applicants who need guidance and mentorship, with a focus on working with marginalized communities.

This decision came from experience. Montgomery’s parents, both in the military and her mother a Jamaican immigrant, weren’t familiar with college admissions in this country. “Thankfully, I had a teacher who was able to help me with the process and I ended up becoming the first student from my high school to go to Princeton.”

Her nonprofit Barrier Breakers supports first-generation students and those facing other challenges to education. It has assisted more than 7,000 students across the U.S. with their higher education ambitions, and has also helped them secure more than $490 million in scholarship aid awards. Montgomery adds that 95% of the law school applicants she helps will be first-generation lawyers.

“We continue to check in with students throughout college — helping them navigate transitions, apply for internships, and stay on track through graduation. Our mission is long-term student success, not just college access.”

— Sydney Montgomery ’15

Around 85% of students have been served pro bono or through the organization’s partnerships, and its funding comes from a variety of paid services, grants, and donations.

Barrier Breakers doesn’t do SAT prep but instead focuses on “holistic college counseling and law school admissions advising, by supporting students through every aspect of the college admissions process and beyond,” Montgomery adds. The team helps students build a balanced college list, assists with academic course tracking and extracurricular activity planning, guides them through the completion of financial aid forms like the FAFSA and CSS Profile, and prepares students for interviews.

“But our support doesn’t stop once a student hits ‘submit,’” Montgomery adds. “Through our Outreach and Wellness Program, we continue to check in with students throughout college — helping them navigate transitions, apply for internships, and stay on track through graduation. Our mission is long-term student success, not just college access.”

She describes Barrier Breakers as “high-touch” in the sense that most of its high school students meet with advisers up to 30 times over two years, and receive continuous support throughout college.

She says a common challenge for students is being overwhelmed by the requirements. “What we do is provide a clear road map for students, no matter their background or socioeconomic status, and hold their hand every step of the way so they no longer feel overwhelmed or inadequate in the process,” Montgomery says. “Students need a champion and they need someone to believe in them and realistically give them tailored and specific advice for their circumstances.”

Montgomery and her staff also work closely with students on essays required for college applications. “Most students aren’t great with time management,” she adds, “so we make sure they don’t start an essay a day before it’s due, and we try to give them the self-esteem they need to write about their main achievements, what their main story will be.”

Staff members also support students by calling them each semester to identify any challenges they are facing. Additionally, Barrier Breakers offers a virtual platform for students to join, and the organization recently launched a regional ambassador program to increase the number of in-person meetups it organizes every quarter.

Montgomery is particularly proud of working with law school applicants who come from marginalized communities. “We’ve seen how they’re not getting the support that they need through law school, and they may be struggling to pass the bar. That results in the U.S. not actually increasing [the] percentage of Black lawyers in this country,” she says.

What Montgomery finds especially fulfilling about managing Barrier Breakers is seeing a virtuous cycle continue to run its course long after the first meeting with a student. “I have always believed first-generation students drive business success,” she says, noting that supporting a first-generation student creates a ripple effect because those students usually go on to support other first-gen students and so on.

Montgomery says her enriching experience at Princeton largely influenced her passion for helping students reach their higher education goals. “I feel like Princeton, more than any institution, gives its undergraduate students the resources to pursue whatever venture they can think of,” she says. “It makes you feel invincible in ways that I don’t think other schools do because they don’t allocate the same number of resources per student.”