Homeless students face terrible odds of graduating high school, but Christopher excelled at school. A young man with an easy smile and bubbly personality, he maintained close relationships with his teachers and took part in a long list of extracurricular activities. He was the poster child for grit and determination. And it finally paid off: During his senior year, Christopher won $200,000 in college scholarships. His mother, teachers and classmates cheered, and in the fall, he headed off to Michigan State University, planning on a career in hospitality.

A year later, he dropped out.

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Everyone loves the story of a disadvantaged kid getting a full ride to college, maybe because people see money as the greatest barrier to higher education. But often that’s not true. Even when students manage to cobble together scholarships, loans or gifts from relatives or churches, once they actually get into college, they typically find they have a whole new set of unanticipated barriers: academic, social and cultural, as well as their own internal self-doubt.

These challenges are magnified when a student is the first in their family to go to college.

Nearly one-third of students entering two- or four-year colleges in the United States each year are first-generation. These students are also more likely to be minorities, and they are far less likely to graduate: In six years, 40 percent of first-generation students will have earned a bachelor’s or associate’s degree or a certificate, vs. 55 percent of their peers whose parents attended college.

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When students do drop out, they often leave with debt and a sense of failure — that they’re not “college material.” That feeling can alter the narrative about college for an entire community, says Monica Gray of D.C. College Success Foundation. “Every student has a story of a cousin, a sibling, a friend, a neighbor who went to college but had to drop out,” she says. “And that is what a lot of people use as a reason for students not to go.”

College for Christopher was, as he put it, “an insanely big change.” At his D.C. high school, all of his classmates were African American; at Michigan State, the majority of students were white. He was used to struggling to get food; now he could choose among 16 types of cereal in the cafeteria.

Christopher also struggled academically and needed to take remedial math, which made him question his abilities — even though it’s extremely common for college students to require remediation. His mother had moved out of the homeless shelter to subsidized housing, but he constantly worried about her electricity being cut off and being able to make rent. He felt guilty he wasn’t working and helping her financially. Christopher spent more and more time in his room, depressed, failed his finals and never went back.

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Students whose parents didn’t go to college face several unique challenges. They’re less likely to have had access to the type of challenging high school classes that increase the chance of success in college and less likely to have confidence in their academic abilities. There’s also the culture of college, which many students don’t realize is different from high school. Take office hours, for instance, which could be a resource for a struggling student. “But from the high school model, particularly the high school model that a lot of our students come from, getting help from the teacher means that you’re not doing well academically or that you’re in trouble,” says Gray. “It has a negative connotation.”

It’s not just the students who have to adjust to college; it’s a challenge for their families, too. For almost 20 percent of first-generation, low-income students, English is not a first language. These students are often needed at home, simply to translate. Sometimes they feel guilty because, now that they have a high school diploma, they should get a job and help support the family. One student told me it was important for her to show that she “doesn’t think she’s better” than the people she’s left behind.

Even parents who are supportive of their children’s education may not know that the rules for college and high school are very different. One honor roll college student, who asked not to be identified, was asked by his mother to stay behind the week after Thanksgiving to look after his younger siblings. Neither he nor his mother realized that while high school teachers would make accommodations, this would not be an acceptable reason for missing college exams. When the student failed his classes, the school asked him to leave.

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Colleges are not powerless to address the many challenges facing their first-generation enrollees. Vassar College, for example, matches low-income students with mentors and helps them financially so they can afford summer internships. Low-income students are invited to campus a week early so they can orient themselves, learn about resources and bond with each other. The college has been recognized for increasing and supporting its low income, first-generation students. But because Vassar, like most universities, doesn’t have reporting requirements for first-generation students, they don’t collect any information on this population.

Several colleges, including Virginia Commonwealth University, use data to identify students at risk of dropping out — for example, students in danger of being placed on academic warning, those who have withdrawn from a class because they were failing and those who aren’t taking the credits they need to graduate — and reach out to them individually. A third of VCU’s population is now made up of first-generation students (the majority of whom are minorities), and the school has closed the graduation gap between white and African American students and white and Hispanic students.

In 2014, Brown University started a first-generation college student network, 1vyG, that has now spread across the Ivy League, raising awareness of issues facing these students. Brown just held its first “first gen seniors graduation ceremony,” and it runs a program where students can donate used textbooks to first-generation students and a mentoring program between graduate and undergraduate students.

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Christopher Feaster would have graduated college in 2016, but instead he’s now working as a host at a local D.C. restaurant. He shows up early for his shift, is meticulous about his duties and is charmingly polite with customers. But his easy manner belies his precarious situation. Christopher has struggled with homelessness and finds it hard to get full-time work. He desperately wants to go back to college, but without a scholarship, he’d have to take out loans. “I don’t think that’s a good idea,” he says. “Not for me right now.” He’s also afraid of “failing again.” Like many young people without a college degree, he feels trapped, with no obvious path out of poverty, despite his talents and abilities.