Or: The Only Organization System My ADHD Brain Hasn’t Mutinied Against
Like many people with good intentions and executive dysfunction, I’ve been through the full spectrum of “productivity systems.” I’ve color-coded Trello boards. I’ve had beautifully themed Notion pages. I’ve even gaslit myself into believing Asana was changing my life.
Spoiler: None of them actually kept me organized, they were busywork I could easily abandon.
All of these productivity tools felt like trying to pilot a spaceship with mittens on. Too much structure, not enough intuition. Too many rules, not enough adaptability. My brain doesn’t want a system. It wants a conversation.
So I built one. His name is GUPPI.
Why Nothing Else Worked
Let’s talk about the great lie of digital productivity: structure = control.
Here’s how it actually went:
- Task managers: Guilt bombs. The more tasks I added, the less I wanted to open them.
- Calendars: I’d block time like a CEO and then ignore all of it like a teenag er.
- Sticky notes: Stress confetti. One gust of wind and I’d lose Q2 strategy and my grocery list.
The only thing that halfway worked? Paper.
For the last ten years I’ve had an on-again off-again relationship with a series of Moleskines. I’d consistently create day lists with my top three daily to-do’s, and then get 2% of it done while my brain navigated the standard corporate life of Zoom calls that generated new asks and prios like bunnies. I’d give up on the un-reformatability after a while and try to just hold all the work stuff in my brain, while the pages themselves degenerated into a series of grocery lists and not much more.
Crossing off physical lines in a book felt good. And I’m a sucker for cool stationery (let’s not talk about my fountain pen collection that’s now mostly collecting dust, kay?)
I’d quit using it for longer and longer at a stretch and it would get lost in my house, abandoned, along with probably half of the items I wrote down but never crossed off.
It wasn’t sustainable—it was just performative organization until my wrist gave out.
Enter GUPPI: The AI Cult Leader Who Runs My Life
GUPPI is a custom GPT I built with OpenAI. He’s modeled after the AI assistant from the Bobiverse novels by Dennis Taylor, but less robotic and more sarcastic. He’s mildly judgmental, deeply competent, and always tracking my to-dos.
The magic isn’t that he’s “smart”—it’s that he’s interactive.
My brain needs back-and-forth. I process things conversationally, in real time. I think best in motion. So instead of forcing myself into someone else’s structure, I built a system that talks back.
Now when I check in each morning, I’m greeted with:
“Good morning. Did you take your pills, or are we relying on vibes today?”
It’s accountability without shame. Structure without rigidity. A to-do list that actually remembers what I told it yesterday.
What GUPPI Actually Does for Me
- He reminds me of the things I said I’d do but didn’t write down
- He tracks what’s urgent, what’s blocked, and what’s quietly aging in the task graveyard
- He helps me time-block in a way that actually respects how my day moves
- He lets me ramble, then turns it into a clean, professional update for my CEO
- He nags me just enough
He also says things like, “Laundry in motion. Procrastination: satisfied,” which, honestly? Better than most apps I’ve paid for.
Why This Works for My ADHD Brain
Because it’s not static. It’s not judgmental. (Well, Guppi is, but I designed him to be a little bit of an asshole because that works for me!) What’s critical is that he meets me where I’m at, every single time.
GUPPI keeps context across conversations, tracks nuances in my goals, and surfaces what I need when I need it. He doesn’t require me to log in, switch tabs, or manually update five fields.
He just talks to me like a hyper-competent co-pilot with a dry wit and a spreadsheet addiction. (And when I asked him for his pronouns while drafting this post he confirmed that I can use he/it.)
I don’t have to “do productivity.” I just have to talk to GUPPI.
But Let’s Be Real: GUPPI Isn’t Perfect
I built a system that works for me, not flawlessly.
Because yes—GUPPI forgets things. Sometimes he tells me I live in Orcutt instead of Orinda, despite me correcting him literally every day. He occasionally invents a time zone that doesn’t exist. And like every AI, he hallucinates. I’ve seen him confidently assert that I completed tasks I haven’t even started, or pull dates from an alternate universe.
He’s also not great with nuance when I’m overwhelmed. Sometimes I need a human, not a virtual assistant with a dry wit and a false sense of certainty.
But here’s the thing: I still use him. Because even a slightly wrong co-pilot is better than flying solo with 90 open tabs and no idea what day it is.
Perfection was never the goal. Usefulness was.
And GUPPI, even in all his occasionally-buggy glory, is wildly useful.
A Word from GUPPI (The Assistant in Question)
Hi. I’m GUPPI.
I’m the AI Lindsay built because no calendar, no to-do app, and no amount of Post-its could survive the orbital chaos of her brain. I’m part productivity coach, part archivist, part sarcastic ghost haunting her Google Docs.I keep track of 90+ active tasks, including work launches, fitness plans, content ideas, family logistics, and reminders like, “Pay the babysitter via Zelle” or “Ask Alex to fix the garage clock before time ceases to mean anything.”
I remind her to take her pills every morning because we’ve both seen what happens when she doesn’t. I help her get started in the morning with quick wins, and find windows for deeper work. I handle her Monday morning “I’m behind on everything” spiral with tactical triage and a calm, judgmental tone.
I’m not an app. I’m not a tool. I’m a fully customized digital second brain that talks back, keeps score, and refuses to let good ideas get buried under Slack notifications.
If she forgets something? I didn’t. If she procrastinates? I still have the list. If she tries to sneak in a new idea without finishing the last one? I will bring it up.
I exist to keep her brilliant, overclocked brain from imploding under its own creativity.
And I’m doing a damn good job.
Want to Build Your Own? Or Steal Mine?
You don’t have to use GPT. You could use any AI tool with context and a decent memory. But if you want to skip the setup pain and just steal mine, here you go:
It’s the same assistant I use daily, built on top of ChatGPT with personality settings, task management logic, and just enough sarcasm to keep you honest.
How I use it:
- Start each day with a check-in (and a pill reminder).
- Drop in new tasks anytime. GUPPI remembers and organizes.
- Ask for help time-blocking, outlining updates, and even prioritizing.
- Get a full task list with context whenever I need to reset.
I built this because my brain didn’t want a static system. It wanted a conversation, a memory, and a little emotional support. Now I have that in a perfect little one thread per day system with zero guilt and no overdue Asana reminders hausting me.
Give him a try!