Work is Weird Now

S5E3: How do we design a work life that’s uniquely ours? With Charlie Rogers


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What if the safest career move right now is… refusing to be one thing?

In this episode, Alice Phillips and Dan Emery are joined by Charlie Rogers, founder of Undefinable Life Design and author of a new book launching this March.

Charlie introduces the idea of the “undefinable” — people whose working lives don’t fit neatly into a single job title, industry, or identity. Not because they’re unfocused, but because they’re layered.

Against a backdrop of AI acceleration, job instability, and the slow collapse of the linear career ladder, Charlie argues that being meaningfully unique across several things is more resilient than being average at one. He calls it the automation of the average — and explains why your edge now lies in synthesis, lived experience, and perspective.

We explore:

  • Why traditional career labels are breaking down
  • The Undefinable Ascent: a practical framework for designing work that actually holds up
  • The case for being “semi-pro” in multiple things, not obsessed with one
  • Why energy, not ambition, is the missing piece in most career advice
  • What organisations need to learn as careers become less linear and more ecosystem-based

This is a conversation about clarity without confinement — and designing a working life that’s sustainable, human, and genuinely yours.

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Work is Weird NowBy Danielle Emery