25 years ago, I was working as a sysadmin for a dial-up ISP and today, I lead the Cloud Native developer experience group at VMware. Spoiler alert: my day to day tasks haven’t changed all that much. How have we progressed over the past quarter century and what clues does that give us for what’s coming in the future? The journey so far has been rocky but still productive and fruitful. In this talk, I’ll highlight how we’ve progressed so far, how the DevOps movement has moved our industry two steps forward and one step to the side, and why the 10 year anniversary is an important milestone.