What happens when using AI feels like something you have to confess?

In this episode, Sean and Matthew start by doing something long overdue: actually defining phenomenology for the audience. They trace the philosophy from Husserl's "back to the things themselves" through Heidegger and Merleau-Ponty, making the case that the question "What is it like?" sits at the heart of everything they do on this show.

From there, the conversation turns to a tension both hosts are living with: being critically engaged AI users in spaces where people tend to read you as either all-in or completely opposed. Sean describes navigating grant applications and IRB submissions that require opposite framings of the same project. Matthew shares the discomfort of discovering a new friend is staunchly anti-AI and wondering whether to compartmentalize a major part of his life. The word they keep coming back to: taboo.

Their guest this week — appearing under the pseudonym Perry Winkle — embodies the complexity of that taboo. A longtime instructional designer now working in product management, Perry has built a sophisticated AI practice centered on Claude, Perplexity, NotebookLM, and Beautiful AI. But what makes this conversation distinctive is Perry's clarity about where the line sits. They describe a deliberate shift from using AI as a vending machine to treating it as a thought partner, building rubrics to have AI check their own learning rather than generate output for them.

Perry's hardest line is reputation. They won't release work that doesn't carry their fingerprint. They won't hand autonomous control to an agent. And when a collaborator sent them a clearly AI-generated text message — in a relationship Perry had invested real relational capital in — the damage was immediate and lasting. As Perry puts it: AI can't replace the social capital, trust, and presence that make relationships real.

In the debrief, Sean and Matthew take this into deeper water. If reputation is how identity gets perceived by others, what does it mean that AI is reshaping both? They explore the phenomenology of writing versus speaking, ask whether a student's conversation with Claude could serve the same purpose as a traditional paper, and somehow end up back at Plato — who wrote philosophy as dialogues and whose teacher Socrates warned that writing itself would destroy memory. Sound familiar?

Thanks for listening, and as always you can find us:

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