Coffee has long been woven into the fabric of Filipino culture, not just as a beverage but as a way of life. For centuries, it has been a staple in Filipino households and a significant source of livelihood for many local farmers. Across the archipelago, coffee is more than just a morning ritual—it is a symbol of community, hospitality, and tradition. In particular, the coffee shop business has seen remarkable growth, driven by changing consumer lifestyles, urbanization, and the increasing popularity of café culture. However, behind this booming industry lies a complex landscape of challenges that entrepreneurs must navigate. This research study aims to explore the intricate dynamics of the coffee shop business by examining the evolving challenges faced by entrepreneurs at various stages of business development—namely, initiation, planning, execution, and control. It seeks to understand how these challenges emerge and transform over time, and how entrepreneurs respond to them.