Chicago City of Learning: A Conversation with Sybil Madison-Boyd

Q&A   22 September 2016
By Sybil Madison-Boyd


We are enabling youth to connect in- and out-of-school learning in ways that support their pathways to college and careers.

Sybil Madison-Boyd
Digital Youth Network's Learning Pathways Program Director, Chicago City of Learning Initiative

Q. Chicago City of Learning (CCOL) is only in its third year of existence, but its growth has been accelerating at an exponential rate. How did CCOL start out? What is the relationship between CCOL and Digital Youth Network?

A. Sybil: The idea for CCOL actually emanated from the city’s response to the teachers’ strike in the Fall of 2012. At this time, many of the city’s youth-serving agencies and organizations came together to support youth while school was not in session. The idea was that this same network of organizations could unite again to support youth engagement in robust learning during the summer and prevent summer learning loss.

Although we certainly experienced some failures, the successes of the first summer supported the need for a year-round focus on connecting youth to “24/7 learning,” and Digital Youth Network (DYN) was ultimately asked to be the local steward of CCOL.

In the beginning, we were clear that CCOL was an infrastructure for supporting a connected learning ecosystem, but our initial message didn’t express this clearly. We initially introduced CCOL as a digital badging initiative, so we have spent a lot of time refocusing our message to the learning itself and how we make the city’s informal learning opportunities visible. We are enabling youth to connect in- and out-of-school learning in ways that support their pathways to college and careers. For us, digital badges are simply a tool that serves to connect learning that is taking place 24/7 and across multiple spaces.

Q. It’s great to see how readily you and your team recognize the successes and challenges CCOL has faced. Particularly given Chicago’s size, what other challenges have you faced?

A. Sybil: The scale of the work is overwhelming. Our goal is to make all informal learning opportunities visible, so that’s a job that takes a lot of time for us. Not only to find organizations and bring them on board but also for organizations to integrate the time it takes to participate, while already managing a packed workflow. We are constantly working on how to sustain and expand this community of youth-serving organizations, which we affectionately named “Chi-Y.O.U.”—Youth-Owned-University.

As we begin to get better data about where these learning opportunities are available in the city, we can get better at responding to this information. We have begun to identify “learning deserts”—places where particular programs are noticeably absent. For example, last summer, we started to look at where Chicago’s coding programs were and discovered many were not free and most were located downtown and/or in more affluent neighborhoods. In response, we applied for and received funding through Best Buy to bring coding programs to some of those “learning deserts.” Our DYN Design Lab is a van that brings laptops, wi-fi, and mentors to neighborhood parks, libraries, and organizations to engage youth in coding and making. We know as we continue to get better at populating the learning ecosystem, we will continue to identify concerning trends, and we look forward to supporting community stakeholders in developing innovative approaches to addressing those concerns. 


This work has been really exhilarating for our team. We have been humbled by the commitment of the 100+ youth-serving organizations that have partnered in this work.

Sybil Madison-Boyd

Q. Although you are continuing to push for more and more growth, how does it feel to be part of something that is already growing so quickly? How would you say your team’s experiences have prepared you for this moment in time?

A. Sybil: This work has been really exhilarating for our team. We have been humbled by the commitment of the 100+ youth-serving organizations that have partnered in this work. We have been inspired by the possibilities to help the city get exponentially smarter about how they are connecting every Chicago youth to existing learning opportunities. And, we are continually challenged to work in ways that result in Chicago’s youth connecting to robust, informal learning and translating those experiences and achievements into new opportunities.

DYN was uniquely prepared to lead this work. We had past experience implementing innovative, large-scale initiatives like YOUMedia, which resided in Chicago Public Library spaces and was eventually scaled across the country. Overall, DYN started as an after-school program trying to address the digital divide between kids from less and more resourced communities through interest-based learning and digital media making. We have long believed the experiences youth have in informal settings equip them with dispositions, knowledge, and skill sets that should be recognized and leveraged in formal academic arenas. As early adopters of digital badges, we gave youth the “capital” to show off their achievements in formal settings. The composition of our team enables us to bring a diverse set of expertise and experience to the huge task of leading a city-wide initiative with so many moving parts. We have felt honored to be in the position to support the city in this ambitious effort.

Q. As you and your team work to inject Chicago’s energy and vibrancy into kids’ learning experiences, what have you been most excited about? Is there a story that stands out to you?

A. Sybil: Our team has been most excited about youth more easily exploring their interests all over the city. We also get really excited about the portfolio of experiences we’re enabling youth to build—a portfolio that helps them keep track of their participation and achievements and that points them to more opportunities to engage broadly and deeply.

One story that stands out to me happened during our very first summer. One of our partner orgs was doing a 5-day architecture program that involved redesigning a specific public area in the city. Youth worked all week long with architects from Chicago and Canada, working through a complete cycle of the design process and, ultimately, presenting their ideas and prototypes at a culminating celebration. I attended the celebration, and one of the program mentors told me about a young African American male participant who attended a local charter school and knew about the program because his teacher had found it on the—at the time—Chicago Summer of Learning website. She said, on the first day of the program, it was pretty clear he struggled with math—he stood out among his high school peers as needing a great deal of support. However, he also stood out among his peers as having superior design thinking skills. We talked about how important it was for both him and his teachers to know this. Especially if he was seen—and saw himself—as a remedial math student at school. That perception was limiting his ideas of what he could do. In that moment, we were both amazed at how this initiative both connected this young man to an opportunity he might not have known about otherwise and provided him with digital badges that could communicate back to his teachers what he was capable of accomplishing.

Q. What a great story! Could you go further in explaining how this young man’s learning—and that of others—is reflected back to the school system?

A. Sybil: Youth’s CCOL accounts are actually digital portfolios that keep track of their participation in and accomplishments from programs that CCOL partners provide. In partnership with Chicago Public Schools, every PK-12 student has an account waiting for them to set up, so they can build their portfolio from a very young age.

Youth can share the contents of their portfolio in a couple of ways right now. Any badge that has been earned can be shared via email and/or social media, printed out as a physical certificate, and/or downloaded. Just recently, in partnership with Chicago Public Schools, we introduced a new feature where youth can now publicly share their entire portfolio—as opposed to single badges or experiences. Part of our job with youth is to increase their “badge literacy” so they understand what kinds of data are packed inside any badge they earn and why and how to share a badge with others.

In addition to youth-driven methods of reflecting learning back to schools, we are engaged in partnerships with the district and teachers in which students’ participation in out-of-school programs and online learning pathways is recognized in the classroom. In partnership with the Chicago Public School’s Office of Civic Engagement and Service Learning, we work with CCOL organizations whose high school programs meet the criteria for the district’s service learning requirement. After a formal application and approval process, these organizations’ badges are then endorsed by the district and “unlock” service learning credit for the youth who earn them. We also have developed online pathways that connect in-school and out-of-school learning. For example, our Young Author Playlist is designed to support the development of creative writing among 7th-12th graders. We have partnered with teachers who use the playlist as a core or supplemental activity in their curriculum, such that youth engagement online “counts” in class.


In partnership with Chicago Public Schools, every PK-12 student has an account waiting for them to set up, so they can build their portfolio from a very young age.

Sybil Madison-Boyd

Q. What new things does CCOL have in store for the next five years?

A. Sybil: Our beloved Brother, Mike Hawkins’ response to this question would be “Revolution!” We are excited about the work to come. After three years, we feel we have reached a threshold that enables us to develop and grow the work in deeply meaningful ways. CCOL is not a household name yet, but we have enough partner organizations, active account holders, and a strong partnership with the school district and city agencies to build deep connectivity for our youth across organizations, learning spaces, and opportunities. This really addresses the opportunity gaps we see across kids, schools, families, and communities.

Our vision for the future includes developing a truly open data platform for informal learning opportunities, strengthening the utility and power of youth’s portfolios as documentation and recommendation engines, increasing the interconnectivity of informal and formal learning in partnership with schools, and using CCOL data to help the city, organizations, educators, caring adults, and youth to get smarter about utilizing, distributing, and accessing the city’s rich learning resources. There’s a lot of work to do, and we’re excited about doing it in collaboration with numerous partners!

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