This document discusses developing a future-proof IoT roadmap for connected devices and data. It notes that without context, data is meaningless, and that IoT is affecting all industries in varying degrees. The journey begins with basic connectivity, then enables data analysis and classification, leading to more complex analysis. Success involves embracing IoT strategically, thinking big but starting small, crawling before walking and running, and embracing the emerging digital ecosystem. An example case study describes a self-serve frozen yogurt machine that lowers barriers to entry through automated operation and real-time monitoring.