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Four Lessons I Learned at City Year


I’m Lily Proudman and from 2018 to 2020, I served as an AmeriCorps member with City Year Chicago. I grew up in Wisconsin but wanted to move to the East Coast to escape my small town. I ended up attending American University, and majored in international relations with a minor in communications. During college, I was a member of Alpha Phi Omega, which pushed me to explore DC and see the city from different perspectives.

When I discovered City Year, I was living in Minneapolis working for Outward Bound in their marketing department and wanted a break from the office environment change of pace. Those two years serving with City Year Chicago helped me to understand I like to immerse myself and learn experientially in new environments.

Here are four things I learned during my service with City Year:

1. The quality of your relationships determines your service experience.

When I walked into Roberto Clemente High School in Humboldt Park on the first day of school in September 2018, I had no idea what to expect. The students were busy catching up with each other in small groups outside the school while others were sizing us up. We were out of place with our red jackets, but teachers approached us and thanked us for being there.

We were present in the various classrooms, in our City Year team room where we held tutoring sessions and in hallways so students could use us if they needed to chat or take a break. For example, I had an amazing relationship with my partner teacher who taught World Studies because I communicated expectations early on and students could tell we got along. I had six out of eight class periods with students and had to learn 150+ students’ names within the first few weeks of school. I took the time to learn a fun fact about each student and surprised them when I saw that student in the hallway. Students liked being asked questions that weren’t school related, and it gave them permission to stay curious about others around them.

2. Take the time to get to know the community you serve.

Choosing to move to serve with one of City Year’s 29 U.S. sites can be daunting. Chicago sometimes makes headlines for negative reasons, but I chose Chicago because it allowed me to see the city through a high school student’s eye. My students had experienced discrimination and hostility from different neighborhoods around Chicago while commuting to school, which caused them to make assumptions about actively choosing to visit or travel there via train. I actively noticed a difference in how wealthier students living 15 minutes away from the school were experiencing a different Chicago than the students I worked with due to access to resources. Students in wealthier areas had stronger academic support and could use that support to apply to competitive universities.

Soon after starting service, it became clear that the school was a pillar in the community, known for being an important center of Puerto Rican life and culture in Chicago. I attended events in the neighborhood, such as the Puerto Rican People’s Day Parade and Puerto Rican Festival. I often saw students attend the festival with their families or participate actively in the parade. Many students’ parents had attended Clemente in the past, and their children attended the same school, cultivating a sense of pride.

I became an active fan of basketball and baseball games throughout the two years I was there and managed to engage with others. I often motivated my students to also attend basketball games to not only support the players but show school spirit! This often-looked like students wearing Clemente hats and shirts to let the other team know who attended what school.

3. The students we serve are not a monolith. Get to know them.

For me, it was especially important to try to get to know the students I worked with because I wanted them to know that I cared about them as whole people, not just students.

I would walk my students to class, lunch, and to certain after school activities. We would chat about their day, any homework they struggled with, and their friends. That allowed us to have something to talk about the next day if I saw them in the hallway. Over time, students in all grades expected me to attend their games because having a fan club shout their name from the stands was nice! They would break out a smile and wave to let me know they saw me. My presence boosted their morale, and I got all the insight into student interactions.

4. Learning to lead with grace.

During my two years with City Year Chicago, I learned a lot about my leadership and working styles. I like to be independent when working on tasks, but I also like to ask how my actions and work are impacting the bigger picture. Asking why matters but explaining why to my teammates is equally valuable, too.

Both service years presented challenges for leadership, but the students who saw me shift positions rallied behind me and were a constant reminder of why I chose to come back. Teachers, students, my team, and security guards showed up differently daily. My job was to create a space where everyone could express their feelings in a conducive environment.

I will always be proud of my time at City Year as an AmeriCorps member. My ability to develop relationships, immerse myself in an urban environment, surround myself with a younger generation, and challenge myself to discover my leadership skills will always be a highlight in my career path.

Navigating life in your twenties comes with its own challenges, but I am happy that through City Year, I became passionate about inequities in urban education and was able to focus my energy on becoming a part of something greater than yourself.

Lily Proudman, City Year Chicago ’19, ’20, is a national marketing and communications summer associate at City Year HQ. She completed her undergraduate degree at American University and recently graduated from Northwestern Medill’s Integrated Marketing Communications Master’s program. She is actively interested in pursuing marketing and communications opportunities in the healthcare field.

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