Traditional advice about radical changes often focuses on “the grind” and defines success as a destination. This talk presents an alternative approach: using your lack of expertise as an opportunity to get cozy with the un-cozy. Drawing from my lab work to data science transition, I’ll share how deliberate practices like journaling, community engagement, and adaptive goal-setting transformed learning from a painful long-haul to a sustainable + valuable journey — plus, how to track said practices with Obsidian.