Photo of graduation caps from Shutterstock.

Over two decades ago, Tenille Warren was a student at a high-poverty junior high school in Southeast DC. Last week, at the age of 37, she started college. What happened in between holds lessons for anyone trying to improve educational outcomes for low-income students.

According to a story in Sunday’s New York Times, when Warren was a student at Kramer Junior High—now Kramer Middle School—a local philanthropist “adopted” her and many of her classmates through the I Have a Dream Foundation. At the time, Kramer was DC’s second-lowest-performing junior high.

At the beginning of 7th grade, half of Warren’s class was randomly selected to participate in the I Have a Dream program. These “Dreamers” got a heavy dose of extra support through high school, including tutoring, summer school, and help with basic necessities like food. They also got a promise of free college tuition if they graduated.

Warren, one of those selected, seemed to be on track. After Kramer, she got into the selective Duke Ellington School of the Arts and graduated on time. She dreamed of becoming a fashion designer. But instead of taking up the offer of free college tuition, she took a job at Safeway, cleaning bathrooms and stocking shelves.

Eventually, Warren worked her way up to a better job. But she never entirely forgot her dream. 6 years ago, she returned to it in earnest, eventually moving to New York for an unpaid internship in the fashion industry and taking night school classes in the basics of fashion design.

This fall, 14 years after the offer of free tuition expired, Warren enrolled as a full-time student at the prestigious Fashion Institute of Technology (FIT) in Manhattan. While she’s gotten some scholarship money, she’s also taken out $57,000 in student loans.

While Warren’s story is in many ways an inspirational tale with an apparently happy ending, it also points up the difficulty of engineering a successful trajectory for students living in multi-generational poverty.

Free college tuition isn’t enough, and extra help in school may not be enough either.

Despite the tutoring and mentoring, many of the students in the I Have a Dream program were far from prepared to do college-level work after graduation.

“We realized pretty quickly that we were never going to be able to catch our kids up academically,” the Kramer Dream Class co-director and mentor, Steve Bumbaugh, told the Times. “This was triage. We were trying to keep these kids alive. We were trying to keep them in school.”

And even Warren, who did well at Ellington, found the prospect of college daunting. She had grown up with a single mother who had trouble holding on to a job, and at one point they were evicted. She told the Times she couldn’t imagine leaving DC for college because she was worried about what might happen to her mom, and about her own basic survival.

Aiming high might not always be the best advice.

Bumbaugh said he now regrets urging Warren to head to Parsons School of Design or Pratt Institute, both top fashion design schools in New York, when she was in high school. Perhaps, he says, if he had suggested small steps instead, she would have her BFA by now.

Grit actually is important.

For a while, it was fashionable to talk about the importance of grit, meaning qualities like perseverance and resilience. Now it’s fashionable to dismiss grit as overrated. But Warren’s story is a testament to the power of grit.

Her efforts to get herself on track for a career in fashion have been heroic. Setting her sights on a job with the clothing company founded by the rapper Jay Z, she did everything but stand on her head to get his attention. After FIT rejected her for the second time, she called the admissions office to ask, “What exactly do I need to do to make no a yes?” When she finally got in, she was living in a homeless shelter while working multiple jobs and taking sewing classes.

It’s clear that Warren has grit, but what’s less clear is how she got it and how to instill it in others. It’s possible that the years of mentoring and support she got in her teens helped develop her remarkable resilience. But then again, that didn’t necessarily happen for the other Dreamers in her cohort.

Don’t judge the success or failure of a program too soon, or by only one measure.

By the standards of the I Have a Dream program, Warren would probably be considered a failure, since she didn’t graduate from college within the time allotted by the program. But that would be a vast oversimplification.

The story is also complicated, to some extent, for her Dreamer cohort as a whole: Only 6 of the 67 students in the group earned a bachelor’s degree on time. Even now, only 9 have their degrees. But 4 students from her class are now in college. And 72% graduated from high school or earned a GED, compared to only 27% of the non-Dreamers in their class at Kramer.

The program also may be having positive effects on the next generation. Currently, 18 children of the Dreamers are in college, 3 hold bachelor’s degrees, and two are in graduate school.

Try not to leave a whole school behind.

While Warren’s fortunes have risen recently, the same is not true for Kramer. It’s still one of the lowest-performing middle schools in DC, with proficiency rates of 24% for math and 22% for reading.

To the extent that the I Have a Dream program was able to help Warren and some of her fellow Dreamers, that’s terrific. But if we’re going to change outcomes for students like them on a broader scale, we need a strategy that transforms entire schools—and, as much as possible, their surrounding communities—rather than the lives of a few members of a subgroup.

The story of Kramer’s Dreamers may hold more lessons for those interested in poverty and education: the author of the Times article, Diana Kapp, is working on a book that will trace the lives of several students from the group. I, for one, am eager to read it.

Natalie Wexler is a DC education journalist and blogger. She chairs the board of The Writing Revolution and serves on the Urban Teachers DC Regional Leadership Council, and she has been a volunteer reading and writing tutor in high-poverty DC Public Schools.