Providing students with opportunities to wrestle with and engage with messy, real-world problems can be challenging in traditional, higher education courses. However, for students in helping and applied professions, engaging with challenging problems in a supportive environment is critical to developing their skills and confidence. This paper presents an innovative pedagogical pilot project that utilizes design thinking in the context of a community-engaged applied learning experience to guide students as they worked on a real problem for real organizations. Undergraduate sociology and master's level social work students engaged in the experience during their regular course work. Their instructors coached them through the process. At the conclusion of the project, they reflected on the process and what they learned. These student reflection papers were analyzed using both a deductive and inductive approach. We found three themes present in these reflection papers: skill development, deeper understanding, and meaningful experience. We conclude our paper by describing how instructors can incorporate aspects of this project into their own classrooms.