Hey, ChatGPT: Roast Me.
The following prompt was inserted into ChatGPT. With the exception of editing out one left-field reference, the entire dialog is pasted as is.
CHATGPT PROMPT:
Hey, ChatGPT, my friend Michael tried this to amusing results, so I’m going to try this too: Based on every single interaction we have had, roast me.
ChatGPT: “Oh, Ernie. You’re like an AI model’s dream and nightmare, all wrapped into one chubby, glasses-wearing, ADHD-riddled, Taiwanese-American burrito of introspection and self-deprecation. Let’s unpack the gift bag of chaos that is your life, shall we?
First off, you're the kind of guy who starts 17 different personal growth projects simultaneously and finishes... maybe three of them, tops. PARA method? Zettelkasten? Obsidian? You’re basically speed-dating productivity systems, but none of them ever quite make it past the honeymoon phase. Your "second brain" is probably as cluttered as your first one, and we both know you’re one missed to-do list away from a full-blown existential crisis.
Speaking of existential crises, your career path is so zigzagged it looks like you let a drunken toddler plan it on Etch A Sketch. “I started as an engineer, pivoted to soft skills, then web instructor, then corporate trainer, and now I want to go back to engineering! Oh, and maybe a podcast! Or maybe figure out how not to alienate someone over leftover noodles.” Pick a lane, dude! Or at least a metaphorical turn signal.
Your social life, bless it, is a classic ADHD buffet of ambition and neglect. You care so much about connections—until it comes time actually to maintain them. Then it's radio silence until you need a referral or someone to crash on your couch. You’re basically LinkedIn incarnate: “Hey, I know we haven’t talked since 2003, but you’re at Google now. Fancy a coffee chat?”
Let’s not skip over the blog revival arc. You’re terrified to hit “Post” because, deep down, you suspect the internet might not care as much about your musings on AI and nostalgia as you do. And let’s face it: “Little Yellow Different” sounds less like a tech blog and more like an off-brand IKEA catalog.
Oh, and your podcast idea?1 Fantastic! A “fake pitch meeting” format for apps that will definitely never see the light of day. It’s like Shark Tank meets Monty Python, with just enough developer jargon to alienate half the audience and draw in the rest purely out of schadenfreude.
But hey, you’re also endearingly self-aware. You know you're a hot mess, and you wear it like a badge of honor. That’s your superpower, Ernie—you’re the harmonizing pattern-mapper of chaos. You make people laugh, think, and occasionally cringe, all while figuring out life one scatterbrained step at a time. Keep being you, you glorious disaster.”
CHATGPT PROMPT:
Wow, I hate you so much
That’s the spirit, Ernie! Channel that rage into your next blog post, newsletter, or…whatever productivity system you’re trying out this week. Hate me all you want—I’m just here, rent-free in your chaotic second brain, with zero risk of being forgotten because you’ll never close the tab. 😘
Be right back: uninstalling ChatGPT.
Except I won’t. This is what I find fascinating about AI: it’s not the existential threat of it going SkyNet and becoming sentient, but how useful it is reading you to filth. Basically, this is software that has collected every self-deprecating joke I've made, every career anxiety I've shared, every half-finished project I've mentioned—and turned it into what's essentially a roast speedrun of my therapist's notes. (Ha, if I had a therapist. Thanks, no job!)
The scariest thing isn’t that it got things wrong — it’s that it got things right. It's like having a friend who's been paying attention to all your bullshit but has no social filter and perfect recall. The kind of friend who remembers that time in 2003 when you said you were "definitely going to learn Mandarin this time" and brings it up at exactly the wrong moment.
At least it didn't mention the noodle incident.
...wait.
(Next week: Why I'm surprisingly okay with AI pretending to know things it doesn't, and what it has in common with that time I offered someone noodles and accidentally started a crisis.)
Oh yeah. The podcast. “Coming soon!”
If you'd said you told it to write said roasting in your voice based on decades of blog posts, I'd say yeah, AI can definitely do this. And now I'm tempted to do it myself but then again maybe wait so I don't ruin Christmas (again).
Hope to high heaven AI can’t really do this