We describe an attempt to model an enterprise’s expansion into business adjacencies within the scope of a Master thesis. It was crucial to define a strategy that would allow the Master student to grow with the task (gain experience with modeling), at the same time ensuring communication with the client and proving the ability of qualitative SD modeling to deliver insights. After identifying problem symptoms, the enterprise problem was explored with methods from Chris Zook: ‘Beyond the Core’. Six cases from Zook’s book offering points of entry for the enterprise problem were cast into generic archetypes and presented to the problem owner. Two archetypes belonging to the “Underachievement” class were identified as most relevant for the enterprise problem, viz. 1) underachievement due to long distance between the core and the adjacency, and 2) underachievement due to poor adjacency repeatability. We developed a preliminary system dynamics model embedding both archetypes. The model gives sensible results with basic policies affecting distance to the core and repeatability. The preliminary results have strengthened the client’s interest in the modeling work. Further joint modeling sessions have been scheduled. Work is still in progress.