There has been a significant shift from on-premise data centers to the cloud in the last fifteen years. This process was due to the perceived cost difference between the legacy on-premise data centers and the newer and shinier cloud. Due to a renewed interest in privacy and data sovereignty, many organizations are returning to the on-premise. For the success of such initiatives, it is fundamental to learn from the past and understand how a modern on-premise data center would be structured. I started working in 2004 when almost everything was on-premise, and I had a front-row seat to the migrations that occurred in this period thanks to my roles as a Systems and Solutions Architect. In this talk, we will recap the last twenty years of migrations to learn some key lessons, and then we will analyze what a modern on-premise data center would look like, which technologies might help and which could be risky bets.