In this episode of Thinking Through, Dr. Allison Lester sits down with Dana Stephenson, co-founder of Riipen, to explore how AI is reshaping the workforce and what that means for students entering an increasingly uncertain job market.
Together, they unpack the quiet disappearance of traditional entry-level roles, the limits of skills lists, and why experiential learning matters more than ever. This conversation moves into the complex realm of learning by doing: building confidence, practicing uncertainty, iterating through feedback, and learning to trust your voice. Dana shares how students, educators, and employers can co-learn in real time, using AI to amplify human judgment rather than replace it.
The episode centers on a core question: How do we prepare students for futures we cannot fully see while keeping humanity at the center of learning and work?
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