From implementing enterprise applications at Accenture in the 1990s to my current role as a Staff Engineering Manager at GitHub, I’ve learned several essential lessons about the software industry. These lessons were often learned the hard way as an individual contributor and as an engineering manager. I’ve often wondered what I would say to myself if I could go backwards in time and help past versions of myself become compatible with what I know now. This talk is that conversation. Attendees will learn how to better guide their own careers in software development today from the things I wish I knew in the past.