Week 13, 2026

Supporting exploratory energy

This week I had a string of long, 1-1 conversations with peers in professional transition - people who’ve made quite drastic changes to their working environment, sometimes their living environment, too, after stewing in it for years. Is there something in the air? I feel a lot of optimistic, exploratory energy from them, a sense of reveling in the open sea ahead.

Most of them have asked about AI, in a kind of obligatory way, like they feel they should ask just to make sure they’re not missing out. This is a conversation I’m actually interested in having, but it is not the moment. Their true interest is in savoring their newfound sense of options and their journey of identity transformation.

Reflecting on that pattern, I’m noting to myself to lean into what Fernando Flores calls “conversations of possibility”.

Here are lines of inquiry that would be supportive:

  • What’s become possible for you lately that wasn’t before?
  • Where are you noticing something new?
  • Sounds like you care about that a lot - where does that come from for you?
  • Where does that go, do you think?
  • Is that new, or has it been there for a while?
  • What’s it like, to say that out loud (to me)?
Books
Chip Huyen
O'Reilly Media, 2025
Clay Parker Jones
Simon and Schuster, 2026
David Clutterbuck
Routeledge, 2007
Robert Harris
Random House, 2016