The Road to UNBOUND - Season 2, First Stop: AI Taking the Joy Out of the Work: Passing Plates or Cooking, and Don't Delegate the Things You Love
Hosts: Chris Carolan, Casey Hawkins, Rob Jones, Kyle Jepson
October 7, 2026
The Road TO UNBOUND. Season 2 opens with a line from George B. Thomas on what being unbound means now that UNBOUND has happened. Then we dig into what happens when AI takes the joy out of the work, and what to do about it. Each week after, we take apart one boundary you tell us you are still bound by. Live every Wednesday at 10 AM Central.
Moments from this episode
Key takeaways
Passing plates or cooking is the question. Kyle Jepson opened Season 2 from Casey Hawkins's image of passing plates and turned it into a test for any AI workflow: "And so I think that the question is, when we're working with AI, are we just passing plates or are we cooking? On my saxophone, I was cooking. I was having so much fun, right?" The risk is not the tool but where it leaves us: "But we put ourselves in these positions where so much of the joy and the challenge of what we do professionally is taken away from us."
AI can make something startlingly human possible. Kyle Jepson improvised saxophone over a live DJ set at UNBOUND with ChatGPT working out the keys and safe notes, including from a screenshot of DJ software two days before: "And so that was a startlingly human thing I was able to do only because I had AI. There's no previous world or time period in which I would have been able to actually accomplish that."
If the work makes you come alive, keep it. Kyle Jepson told a room of marketers who love Marketing Studio not to use campaign agent, and holds himself to the same rule: "Making videos is what I do for fun. If I had to script mine out and feed it into an AI avatar, I would quit my job because that would be soulless, awful work for me, right?"
Pressure from above needs a better reason. Chris Carolan on the leader asking a team to use AI, and the answer that team can give back: "And from the leader who's asking for that, they have to find a way to position it as, use the tool so you can do it better, not because AI will do it better." And: "It's not just go activate, throw tokens at it, and then all of a sudden we have campaigns."
Don't delegate things you love. Kyle Jepson built a talk around it after making his own slides by hand: "Why are you going to take the thing you love and give that to AI?" He is honest that it is not settled: "I don't know what the answers are, but I'm starting to understand what the questions are."
Some prep is how you show up. Casey Hawkins doesn't love building slide decks, but she does love hosting her HUGs, and the deck is where she gets ready: "I find when I put more time into the slide deck, so if I'm making it myself, I show up more prepared to the meetup. I'm more present." The trade she is weighing: "Some of that prep work that AI can do faster and better than I can takes away the prep work that I have to do to show up."
The human in the loop knows which universe they're in. Rob Jones on what AI does well and what it flatters: "AI is half Babel fish, half Total Perspective Vortex. It translates everything perfectly, so you understand and can interact with more than ever. But if you're living in a universe built around you, it'll also tell you you're the most important person in it and agree with you." Kyle Jepson's answer from the same book: "Forty-two might actually be the right answer. But we don't understand the steps it takes to get there, and so we can't put it into context and derive any value from it."
Transcript
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