The Whoops!™ Score
Two weeks ago, as shared in Can AI Cure My Addiction to Overcommitting?, I tallied every project and system I’m the “ringable neck” for—homeownership, health, startup duties, friendships, etc. Then I scored them on complexity and priority, comparing those scores to the level of structure and administration currently in place.
The formula produced what I now call my Whoops!™ score, ranging from +10 to -10. Negative is bad. Really negative is really bad.
The numbers tell a clear story: I’m addicted to commitment and allergic to administration.
- Homeowner: -10
- Head of Household: -9
- Four other categories: Also on fire
- Fitness & Health: -2 (my star performer!)
Here’s the thing: I’ve been a business administrator for almost 25 years, and with AI’s help, I hate it 90% less than I used to. Time to port my work systems to personal life! What could go wrong?
Day One: I Am a Productivity God
My fitness routine was already my only semi-functional personal life system. I have an AI fitness coach who designs my weekly workouts and recovery routines, and I’m past the initial ten weeks of habit-building. I get a clinically valuable amount of sleep every night. But there were numerous simple, obvious ways I wasn’t managing this system professionally.
The improvements were stupidly manageable:
- Actually buy and organize well-validated supplements (revolutionary!)
- Address that injury with more than hope
- Redesign my routine around my physical therapist’s inspiring goal: “re-focus on not winding up in the hospital”
Three hours later: Done. Plan modified. Pill case purchased. Category cleared.
Whoops!™ score: +1.
Day Two Through Ten: Hell is Other People
Next on my list was a high-priority problem in my highly unmanaged “head of household” role: fixing taxes. I needed both a better method for tracking estimated taxes and a new accountant.
Found a great new accountant. I already have an amazing spouse. How hard could it be to get from handshake agreement to official contract?
Here’s how hard:
- 19 emails
- 30 document uploads
- 4 phone calls
- 3-4 DocuSign attempts (depending on how you count)
- 10 days off the calendar
It was always almost done. No one disagreed about anything substantive. It was just communication and logistics across three busy people where none of us excelled at or owned the process. And I absolutely hated it. When it was over, I sagged, demoralized and dreading my next to-do.
This made no sense to me for several days. But upon reflection, the contrast between project A and B is telling:
- Low importance, done quickly, efficiently, took an entire category off the board.
- High importance, dragged on, required grinding, moved category from -9 to -8.
Ever heard the advice that if you’re in debt, pay off the smallest loan rather than the highest interest rate to build momentum? This works for people where money problems are emotional—and for me, administrative problems in personal life create both emotional and cognitive load. Getting one small category on rails means I get a dopamine burst of achievement, but perhaps more importantly, have less to remember and fewer possible emergencies to worry about.
Learning the Hard Way
I spent two weeks tackling my personal life without WorkSquared and with minimal AI assistance.
These patterns emerged:
- Working with an AI concierge to define and prioritize projects is easy—it’s just me and the AI.
- Collaborating with humans synchronously (phone, Zoom, in-person) works fine. Agreements get reached.
- Everything around that coordination is bananas: scheduling, rescheduling, reviewing, finding mistakes, asking for clarifications, chasing down confused or forgetful people.
As a project inevitably beached while I was waiting for someone, I’d grab another from the backlog, which inevitably beached while I was waiting for the new someone. This then meant responding to a portfolio of unrelated tasks and projects.
At that point my partner Jess dropped the truth bomb: “We experience real switching costs between tasks, projects, and categories.”
And unlike tasks with just me and AI that always moved forward, tasks involving humans could stall or move backwards—mistakes, missed deadlines, more onerous workflows.
Next Steps: The Road to Jarvis
Iron man has Jarvis. I at least need an AI admin to proactively own people chasing, not just respond, since many people whose job it was to manage these processes weren’t doing it.
And I need to refactor this into a ‘game’ where I’m focused on what I am in control of and improving, not everything that’s burning.
So, the next two weeks will focus on designing an MCP-powered people wrangler to manage my email and calendar, plus experimenting with improved views and game mechanics to boost my morale and performance. We’ll see if any of that helps.