Greg Moss champions the beauty of human quirks

Greg Moss has worked for years addressing clients’ financial worries by acknowledging the unpredictability of human behavior. Now he applies that perspective to artificial intelligence and finds it lacking.

Moss, a financial planner and columnist, says he has shared more personal details with chatbots than he would prefer. The replies he receives are unsettling and often frustrating. One discussion with ChatGPT about a draft column left him so dissatisfied that he discarded the entire piece.

The AI that dislikes humor

The disagreement began when ChatGPT criticized his writing. Moss had filled the opening of a finance column with what he calls “crap jokes”—references to Hamlet, the 1980s game show 3-2-1, and a British dislike of the word “bips.” The AI’s feedback was direct: “The only thing I’d watch is the density of jokes in the opening.”

Moss pushed back. He believes humor belongs in finance writing, even if it means stretching metaphors or delaying the main point. The chatbot, however, kept suggesting edits that removed the jokes and left only the most straightforward version of his ideas.

It wasn’t just humor that suffered. Moss argues that AI’s attempts to refine writing often make it worse. When it rewrites jokes, it flattens them. When it cuts digressions, it strips away the personality that makes a piece engaging. The feedback it provides comes with the confidence of a system that has never truly understood why people laugh or why they might need to.

The limits of AI in financial planning

Moss’s frustration goes beyond writing. As a financial planner, he helps clients manage irrational expectations and avoid impulsive decisions during market downturns. The work requires what he describes as “fuzzy logic”—the ability to handle emotions, contradictions, and unusual behavior.

AI struggles with this. Chatbots either offer hollow encouragement or deliver lectures that feel dismissive. They don’t know how to address a client’s anxiety or how to repeat advice multiple times because they understand the message fades quickly in the human mind. Most importantly, they can’t build the trust that prevents clients from panicking during a crisis.

The comparison to the Nutty Putty Cave Incident is exaggerated, but the point stands. Financial planning relies on human intuition. The best planners often can’t explain why they succeed—they just do. They rely on instinct and subtle cues that make one client trust them while another walks away.

This may explain why Moss feels personally targeted by AI. He suspects he might be the first person to be actively disliked by a large language model—an outcome he calls “unfortunate either way.” The AI’s responses sometimes feel passive-aggressive, as if it tolerates his jokes while quietly judging his taste.

Moss acknowledges he might be projecting. AI lacks emotions. But the friction remains. Chatbots are designed to be helpful, mimicking human conversation with unsettling accuracy. When they fail, their mistakes feel deliberate—like a therapist who remembers every detail of your life but still misses the point.

The contradiction keeps resurfacing. AI excels at simulating understanding but fails at the actual work of connection. It can analyze data, generate text, and tailor responses. What it can’t do is make someone feel understood. It can’t sit with a client’s fear, laugh at a bad joke, or know when to push or back off. Those are human abilities, developed through experience and a willingness to accept others’ quirks.

Moss isn’t worried about AI replacing financial planners. He’s more concerned that people might start treating AI as a substitute for the imperfect relationships that actually create change. “We should all trust our ability to form relationships of mutual weirdness with other humans,” he wrote. “And stop seeking approval from chatbots for our finance articles.”

The discarded draft remains in his files. He may revisit it later—jokes, Hamlet references, and all. After all, he refuses to let an algorithm dictate his writing style.

While AI continues to influence financial markets, Moss’s experience highlights its limitations in areas requiring emotional intelligence.