Advances in generative AI like ChatGPT present new opportunities to improve learning for DevOps practitioners. In this talk, I will demonstrate how to leverage these large language models to build a customized learning assistant that helps you skill up faster. I will walk through creating your own learning assistant step-by-step, showing how it can leverage your team's documentation, tribal knowledge, and online resources to provide on-demand support. This talk will also discuss current capabilities and limitations of AI assistants with a DevOps lens. While powerful, these models still require human supervision for responsibly staying up-to-date on best practices. The goal of this talk is to start a practical discussion around augmenting our learning processes with AI while being realistic about its maturity.