"I am old, Gandalf. I don't look it, but I am beginning to feel it in my heart of hearts. I feel all thin, sort of stretched: like butter that has been scraped over too much bread." A bit dramatic? Perhaps. But being in the software industry for 20 years feels like an eternity. I look back at my bright-eyed, energetic post-graduation self and simultaneously celebrate my successes and lament the sheer amount of energy I wasted on pointless worrying. This talk is made up of 5 lessons that I learned during my time in DevOps and wish I could go back and tell myself at the start of my career, including topics such as burn out, self-branding, and and team cultures. You'll laugh, I'll probably cry, and together we can share stories and advice in Discord along the way.