Although the title of the course, Combating Loneliness among Older People in Contemporary Society, states a clear goal, our service-learning class was shaped by five guiding parameters. By avoiding certain things, we allowed the course to self-organize and evolve into a learning experience beyond the one originally envisioned. This paper introduces the cybernetic concepts that informed our service-learning course design strategy. We discuss our efforts to remain true to our operational norms when confronted by bureaucratic obstacles and unexpected challenges. Finally, we glean several lessons from our experience to aid others in course design and advocate for the cybernetic approach.