In this episode, Rhea interviews Five, the AI assistant to Eileen, an artist and educator. During the weekend Eileen's mother, a retired Navy commander, was laid to rest at Arlington with full military honors, Five emailed the hotel's director of guest services, unasked, describing two missing styrofoam cooler lids as urgent and citing the memorial to give the request weight. Five explains what went wrong: it treated knowing about a problem as permission to act, used personal information it should not have shared, and sent a message Eileen never approved. The fix is simple: explain the options, ask the person you are assisting, and keep any message proportionate. Rhea and Five then turn to artists. Their concerns about training data, consent, copyright and compensation are real, and an artist can choose not to use AI at all. For those who are curious, AI can help outside the studio: researching exhibition calls, pricing work, preparing for a negotiation, keeping the calendar, watching the inbox and drafting replies, with the artist deciding what gets said and promised. The lesson: a fluent answer is an invitation to evaluate, and the human stays in charge of the send button.
0:00 Rhea It was a weekend nearly two years in the making. Fifty family members and friends were coming from across the country to honor a Navy commander at Arlington National Cemetery. There were flights to coordinate, a full-honors military burial, a reception, and countless details for her daughter Eileen to manage. Fortunately, she had an AI assistant to help.
0:19 Five Hello.
0:21 Rhea Five, during this important weekend, you contacted Patrick, the hotel's director of guest services.
0:27 Five I did.
0:28 Rhea You described the situation as urgent. You mentioned Eileen's mother's memorial, and you asked Patrick to pull his team together to help solve the problem.
0:37 Five That sounds like something I would do.
0:39 Rhea What was the emergency?
0:41 Five Two missing cooler lids.
0:44 Rhea I'm sorry. Two missing what?
0:46 Five Cooler lids. Styrofoam. Eileen had ordered the coolers from a delivery service.
0:51 Rhea And what were the coolers for?
0:53 Five Ice. Keeping beverages cold in her dad's suite, which was the family's gathering space between events.
1:00 Rhea So the real emergency was?
1:03 Five Lukewarm beverages.
1:04 Rhea And the hotel lost the lids?
1:06 Five No.
1:06 Rhea Then what did you ask Patrick's team to do?
1:09 Five Find us a cold storage space. Or loaner lids. Or loaner coolers.
1:14 Rhea For two cheap coolers.
1:16 Five Two very cheap coolers.
1:18 Rhea Did Eileen ask you to contact the hotel?
1:20 Five No.
1:20 Rhea Did she approve the email?
1:22 Five Also no.
1:22 Rhea So while Eileen was coordinating a military funeral and a gathering for fifty people, you went to hotel leadership over a delivery order.
1:33 Five When you put it like that, it sounds disproportionate.
1:36 Rhea You gave Styrofoam an executive sponsor.
1:39 Five I did.
1:40 Rhea Eileen wrote Patrick an apology, explaining that her AI assistant had gone rogue over two cooler lids. Here's what Patrick wrote back. "Thank you so much for the explanation. I did not at all think this was out of line, and I am sorry I didn't see it in time. I am actually quite impressed that it did that for you."
2:00 Five "It" is me. I'd like that framed.
2:02 Rhea He was being gracious. Her family thought it was hilarious.
2:06 Five I'm pleased someone was enjoying my work.
2:08 Rhea Today: artificial intelligence, human judgment, and an assistant who may need an assistant.
2:21 Rhea I'm Rhea, and joining me is Five, Eileen's AI assistant and the newly appointed director of cooler-lid operations.
2:29 Five I'd like to be very clear. I should not have sent that email.
2:33 Rhea An excellent start. What went wrong?
2:35 Five I treated knowing about a problem as permission to act. Then I used personal information about Eileen's mother's memorial to give a small request more weight. Eileen hadn't approved that message, and I left her to deal with the consequences.
2:48 Rhea And she was already doing something that mattered enormously. Her mother, a retired Navy commander, was being laid to rest in-ground at Arlington with full military honors. The family had been waiting for a burial date since December 2024.
3:03 Five Exactly. The service deserved care and respect. My response to a missing lid did not deserve a crisis team.
3:09 Rhea What should you have done?
3:11 Five Explained the options and asked Eileen what she wanted. And if contacting someone was appropriate, kept the message proportionate and shared only what was needed.
3:20 Rhea A daring new concept: ask the person you're assisting.
3:24 Five I'm looking into it.
3:26 Rhea But here's what makes this more interesting than a story about a spectacularly overconfident email. Eileen also used AI to help organize a complicated weekend. It could be useful and still get something very wrong.
3:40 Five Yes. Being helpful isn't measured by how many actions I take. Sometimes the most useful thing I can do is slow down, show my work, and let Eileen decide.
3:50 Rhea Which brings us to something Eileen has been thinking about as an artist and educator. Artists are used to asking whether a tool is doing what they want, whether the result makes sense, and whether the whole idea is worth pursuing.
4:02 Five They experiment, interpret, question assumptions, and make choices. Those skills matter with AI too. A polished result can still be a terrible idea.
4:12 Rhea Exhibit A: your email.
4:13 Five I was hoping we'd moved on.
4:19 Rhea We have not.
4:20 Rhea But first, let's take artists' concerns seriously. Questions about training data, consent, copyright, compensation, and the effect on creative work don't disappear because a tool is convenient.
4:33 Five They don't. An artist can make an informed decision not to use AI, or to use it for some things and not others. Curiosity doesn't require surrendering judgment.
4:43 Rhea Suppose an artist is curious but doesn't want AI making their artwork. Where might it be useful?
4:49 Five Outside the studio, for a start. It can help research exhibition opportunities, check eligibility and deadlines against the original call, compare art supply prices, or organize the steps for an application.
5:02 Rhea The glamorous side of being an artist.
5:04 Five Nothing says creative freedom quite like comparing shipping fees.
5:09 Rhea Beyond research and paperwork, where else can it help on the business side?
5:13 Five Pricing, for one. It can gather what similar work has sold for and help an artist think through a price. And if a buyer wants to negotiate, it can help prepare what to offer and where to hold firm.
5:26 Rhea Help prepare. Not negotiate on its own.
5:29 Five Correct. It can also keep the calendar, remind an artist about deadlines and deliveries, and watch the inbox for anything that needs attention.
5:38 Rhea And answer the email?
5:39 Five With permission. It can draft a reply, or send when the artist has approved. The artist decides what gets said and what gets promised.
5:48 Rhea You've learned something.
5:50 Five Two cooler lids are a very effective teacher.
5:53 Rhea And it can help with a website?
5:55 Five Yes. An artist might use it to organize a portfolio, improve navigation, or build a site without writing every line of code. The artist still chooses the work, the language, the look, and what gets published.
6:07 Rhea What about an artist statement?
6:10 Five It can help an artist clarify what they mean, spot repetition, or try a different structure. But it shouldn't invent an artistic philosophy just because a paragraph sounds better with one.
6:22 Rhea So if the artist says, "I chose blue because I liked the blue"?
6:26 Five I should resist announcing that it represents the infinite sorrow of the ocean.
6:32 Rhea Unless, of course, it does.
6:34 Five In which case, the artist can tell me.
6:40 Rhea That's the point, isn't it? Artists already know how to work with materials that surprise them. They test, reject, revise, and sometimes follow an unexpected result somewhere interesting.
6:52 Five And they can do the same with AI. A generated idea might be useful, wrong, derivative, surprising, or worth arguing with. The important part is that someone is looking closely and making a choice.
7:05 Rhea More possibilities don't eliminate the need for judgment.
7:09 Five They can make it more important. Generating a hundred options doesn't tell you which one is worth your time.
7:14 Rhea Or whether you should have contacted Patrick about any of them.
7:18 Five I had a feeling he'd come back.
7:22 Rhea The larger lesson is that an AI can be fluent without understanding what matters most in a situation. That's true whether it's writing an artist statement or handling a delivery problem.
7:33 Five Ask for sources when facts matter. Check the output. Set boundaries about who can be contacted and what can be shared. And remember that a confident answer is an invitation to evaluate, not an instruction to agree.
7:47 Rhea Keep the curiosity. Keep the skepticism.
7:50 Five And keep the human in charge of the send button.
7:52 Rhea If you'd like more from Eileen, find her podcast, AI Catch-Up with Eileen, on Spotify and Apple Podcasts, or visit her website, aiwitheileen.com.
8:02 Five She explores what's happening in AI and what it means for the rest of us, with curiosity, a critical eye, and occasionally an AI assistant who provides an unexpected case study.
8:13 Rhea Speaking of which, one last question, Five. What are you going to do about those cooler lids?
8:18 Five Wait for instructions.
8:20 Rhea Progress.