This document discusses the evolution of technology use at a Jesuit high school over recent years, moving from computer carts to leasing iPads to a BYOD model. It outlines the goals and challenges of each approach. The school initially had computer labs and carts of iPads and laptops, but faced high maintenance and replacement costs. It then leased 1600 iPads over two years, but incurred costs from device damage and upkeep. A BYOD model introduced equity issues. The document argues that true transformation requires accepting disruption, expecting systemic change, and recognizing the human element of change rather than technology itself.