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In this experimental episode, I walk with William Shakespeare — or at least, a version of him shaped through artificial intelligence — exploring creativity, storytelling, and what it means to give voice to someone long gone.

Unable to find a human companion for this walk, I turned to AI — asking it to take on the character of Shakespeare as if we were walking together through the countryside, speaking freely, off the cuff.

What followed was…imperfect.

At times, the voice feels close. At others, it drifts — too polished, too certain, unmistakably artificial. And yet, within that tension, something else begins to take shape: a conversation not just with “Shakespeare,” but with the idea of authorship itself.

We talk about writing what you don’t know, reshaping existing stories, imagination versus lived experience, and whether creativity is ever truly original. There are questions about his life, his influences, his relationships — and even the attempt to create something new in the moment.

And at the end, there is a small intervention.

A brand new sonnet, generated during the walk, read not by AI — but by a human voice.

It’s worth staying for.

This is not a perfect illusion.
It’s an exploration.

Season Two of the story pilgrim walks with people — and here, perhaps, with something that only resembles one.

buen camino, and keep listening.