Chicago Data Stories: Jacob Caplan

The To&Through Project
3 min readMay 17, 2022


Jacob Caplan is a Postsecondary Coach and Teacher at Eric Solorio Academy High School

Here at the To&Through Project, we work to make data accessible with an aim to inspire action. As a result, we’ve often had the honor of being privy to our colleagues’ personal reflections on the data we share, and their varying perspectives shape the way we think about this work.

Below, we share Jacob Caplan’s reflections on one of our Data Insights — which summarize years of research from the UChicago Consortium and To&Through Project — and his pushes for thinking about how students’ voices can inform our collective work to improve the system.

Every year, we have students who express desire to enroll but lose steam over the summer. In some cases, student apathy can be an issue. However, it’s much more common to see things out of students’ control as the barriers that keep them from ultimately enrolling. This can be as seemingly simple as correctly activating an online portal (which can be more confusing than some may think!) or the headache of financial aid verification. These many hoops to jump through to simply get enrolled in school can ultimately lead a student to change their mind and seek a lower-barrier pathway.

I want to see more institutions focus on making enrollment less of a hassle and providing opportunities for students and high school support staff to connect directly with highly effective staff on college campuses. This is particularly important because colleges’ staff make-up, enrollment processes, and first-year support structures can change so much year to year.

These data also remind me that CPS has gotten so much better at providing resources for high schools to support students to enroll immediately after graduation. However, once that window of time passes, students have less proximity to those staff members and resources that can provide them assistance. Then, there are action steps such as locating transcripts, clearing financial aid holds from previous campuses, sending SAT scores, etc. All of these things pile up and make people feel like enrolling later on is too hard.

I think we need to provide practitioners with ready-to-use resources that break this data down in a way that helps students think through a “So what?” mindset. In other words, we need to share these data directly with students and school staff so that we understand the consequences of not immediately enrolling while protecting against the feeling that not doing so means that a college degree is unattainable. Lesson plans and digestible graphics are incredibly useful.

On the other hand, this work is done through small-group and one-on-one conversations, which is time-intensive. We need more opportunities for students to get direct support from the people most familiar with these data and enrollment processes. This can’t take place in a “senior seminar” class period alone. Closer collaborations between high schools, research organizations, and colleges could truly shift how we support students.

—Jacob Caplan, Postsecondary Coach and Teacher at Eric Solorio Academy High School

Check out more of the To&Through Project’s Data Insights and tell us about your own reflections.



The To&Through Project

The To&Through Project aims to increase high school & post-secondary completion for under-resourced students of color in Chicago & around the country.