Travis’s academic journey began much like those of the New Yorkers slated to benefit from Governor Cuomo’s program. In the fifth grade, Travis and his parents received word of guaranteed tuition assistance through a scholarship program I helped launch with the “I Have A Dream” Foundation, the theory being that financial obstacles to college enrollment keep educational inequality entrenched, and that removing those obstacles early will increase the students’ likelihood of long-term academic success. Growing up, Travis, like many of his classmates, believed there was “no doubt” he would graduate from high school and enroll in college, and in the spring of 2009, his family celebrated Travis’ graduation from Hyde Leadership Public Charter School and his admission to Lincoln University in Pennsylvania, a significant accomplishment in a city where at the time, just 43 of every 100 students graduated with a high-school diploma in four years and only 29 enrolled in postsecondary education within 18 months of graduating from high school.

It didn’t work out: For Travis, like hundreds of thousands of students who struggle with the college transition each year, what could have become a heartwarming tale of beating the odds gave way to another, equally familiar story. After completing one semester, Travis returned home with a newfound status: college dropout.

So what happened? There are several commonly offered explanations for why students with Travis’s background struggle academically. In the first, the problem for Travis and students like him is a “culture of poverty” where “low-effort syndrome” or cultural adaptations like equating success in school with “acting white” prevent young people from living up to their potential. In this version, individual students and disengaged parents form the core of the problem. In the second, “structural barriers” like poverty, institutional racism, segregation, and lack of adequate health care block Travis and his peers from accessing equal opportunity. In this narrative, injustice is embedded into the structure of American society itself. Governor Cuomo’s initiative builds on this tradition, creating a policy that will ostensibly produce a new generation of college graduates by removing a key financial burden that stands in their way: having adequate resources to pay for school.

The problem is that neither story is completely right. Over the course of a decade, beginning with two years as a classroom teacher followed by doctoral work in sociology at Princeton University, I witnessed a significant number of students develop a sophisticated logic of underachievement that challenged popular accounts for how inequality in higher education is created and sustained. For many students, their pursuit of long-term educational success was grounded and strategic. Educated in environments that measured academic success primarily by enrolling in college—not necessarily graduating with a degree—they developed strategies to achieve that goal with minimal effort in school. As a result, only two of my former students—now in their mid-20s—have completed a postsecondary degree. These are not the strivers who “realized the impossible” by escaping their cultural surroundings to succeed in college; nor are they disconnected dropouts who failed because they didn’t have access to financial resources. Their untold struggle lies in the vast middle, where the majority of my students grew up fitting neither description.

The goal of the “free-college” movement is, of course, to help more students access the benefits of a college education. To make that happen, it is necessary for policymakers to examine why that’s not happening today. At the root of that story is academic preparation in high school (combining both course rigor and achievement in those classes), the single strongest predictor of college completion according to a landmark study. In other words, the question that matters most is not why students like Travis scale back their efforts on Scarlet Letter term papers. He wrote it in under an hour and earned a grade of 70, dragged down by preventable grammatical and spelling errors. The question is under what conditions those behaviors, when applied to multiple courses over time, make logical sense. “Doesn’t matter,” he told me the morning he turned it in. “I work hard when I want to work hard, and that’s what a lot of people can’t do. Some people might not look at it as a skill, but to me it’s a skill.” I asked him to elaborate. Achieving As and Bs when you can satisfy your family’s expectations and meet your own long-term academic goals with Cs and Ds, not to mention distinguishing yourself in a city where only three in 10 high-school graduates attend college? “I don’t see the point in that,” he said. It’s a sentiment that years later, he wished he could have taken back.