Douglas Freeland became a volunteer tutor with the Cabrini-Green Tutoring Program (now Tutoring Chicago) in 1991, after his Quaker Oats supervisor invited him to share tutoring responsibilities as she balanced a busy schedule. Little did Douglas know that what started as a favor would turn into a meaningful decade supporting underserved students through one-to-one tutoring. After ten years, Douglas left tutoring when his job moved to the suburbs, but he never forgot the experience.

“There was a sense of camaraderie amongst the tutors…We started at the old Montgomery Ward building and we didn’t have an itinerary or agenda, so my starting point was always homework and how I could help.” Over time, Douglas saw firsthand the impact that individualized support could have on a student’s growth. “A key standout memory was taking my first student, Darina, from 2nd grade through 6th grade, and seeing her develop [both academically and personally],” says Douglas. “She was shy at the beginning, but she was committed to getting better and her mother supported her, too…by the second and third year we had developed a good working relationship.” 

Douglas would spend time with all of his students trying to understand their background and experiences, and encouraging them to try new things. One Cabrini-Green student had never been to the lakefront, which surprised Douglas given the neighborhood’s proximity. It was a somewhat sobering moment and part of why he tried to encourage students to push beyond what was familiar. “I would try and get them to expand their mind and I would tell them…you can be a firefighter or a nurse, and see the lightbulb go on.”

Throughout his time with the organization, Douglas tutored two additional students at the Montgomery Ward building and other locations. Beyond geography, he witnessed Tutoring Chicago’s program grow and evolve. “Over time I saw that more African American tutors started to come into the program, which I thought was beneficial for these kids,” says Douglas, “and the program became more professional, more organized…People were always doing good work, but by the time I left, it had become even more organized and detailed.” He observed that the number of students continued to increase year-over-year.

While he enjoyed watching the organization grow and evolve, Douglas found that tutoring changed him, as well. “One skill I learned was patience. My second student was Darius, and he was a little bit of a handful,” laughs Douglas. “He was full on ‘Let’s play’ and I was full on ‘We have to get some work done.’…I grew up in an era where dads were ‘in your face,’ and I realized I had to dial that back and be more accommodating,” says Douglas. “What I’m most proud of is being there for a decade…and hopefully positively influencing the students.” 

For six decades, volunteer tutors like Douglas have been at the heart of Tutoring Chicago’s mission. Their dedication has helped thousands of students strengthen their skills, build confidence and reach their full potential. As we celebrate 60 years, we’re grateful to Douglas and every volunteer tutor who has helped make this impact possible.