I was the regular enterprise sysadmin: network administrator & datacenter systems engineer in an ISP, IT operation support administrator in a retail company and IT systems engineer in a software development company. I spent time on choosing cool names for my servers. I knew the exact location of a server in the datacenter. I felt sad when their lights stopped blinking. I felt more sad it that happened on a weekend night. And then I joined a team adopting the DevOps mindset. Let me be honest: change was scary! But it was also a great learning experience. This talk will share what was challenging and what worked for me in my transition from being a regular sysadmin to living and breathing DevOps.