This as-told-to essay is based on a conversation with Dean Grey, a participant in a program by AI Commons that aims to upskill and retrain workers who have been displaced by AI alongside a monthly stipend. Grey is an entry-level software engineer who is struggling with his job search. I never imagined I would become an early participant in what feels like a social experiment for the AI era. But after spending years trying to break into tech, only to watch entry-level jobs evaporate almost as