Using AI on my own life
I use AI on my own life, and I write up what happens. These pieces cover a property tax appeal filed in a day, a family budget I still check by hand, selling records online, getting ready for an international trip, and a job search.
Some are personal. They cover getting through a family health emergency and a surprise hospital discharge with AI's help, and why getting more done than ever made me uneasy.
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I Fired Rocket Money. Your Company Could Be Next.
· 7 min readI canceled Rocket Money and built my own budgeting system that does more for less. How it works, and what companies like it could do about it.
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I Built a System to Spy on Myself
· 3 min readI built a private location history on my own web hosting to explain mystery charges, and found a dozen other uses for it.
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I've Never Gotten More Done, and It's Making Me Uneasy
· 8 min readWorking by voice with Chief, my AI chief of staff, I got through a huge list of work in one day and never felt a sense of accomplishment. I look at why that much output feels off and the new boundaries I'm going to try.
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A Surprise Hospital Discharge, and the AI That Kept Me Cool
· 6 min readWhen the hospital moved to discharge my aunt with no notice, I talked through the drive in with a Claude project that already knew her case. We built question lists for her doctors, social worker and rehab facility, and every open question got answered.
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I'm Using AI to Survive a Family Health Emergency
· 6 min readFor a month I was at my aunt's hospital bedside nearly every day, and AI helped me manage everything around her care. It explained the monitors, drafted family updates, booked urgent flights and cleared my calendar, though I never asked it for medical advice.
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I Used AI to Prepare for an International Trip
· 5 min readBefore flying to Warsaw to speak at a summit, I talked the trip through with Claude, from getting to the hotel and phone service to translation apps and a half-done Global Entry application. Many answers also covered something I would have run into later.
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Using AI for the Family Budget
· 5 min readMy Sunday budget run pulls every transaction from Rocket Money, checks it, and fills our family spreadsheet, with AI cleaning up merchant labels but never doing the math. The thirty minutes of typing is gone, so my son and I just talk through the month.
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Job Hunting Is Miserable. Put AI on It.
· 7 min readFor people job hunting for the first time in years, I show how to hand AI the labor of the search, from resumes and trackers to applications. Check everything it writes, and keep it out of interviews and the moments that have to be you.
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I'm Using AI to Sell My Records
· 8 min readIn five days I built a system that makes finished eBay listings from loose phone photos of my old DJ records. The same tool spent days claiming it could grade condition from photos when it couldn't, and rewrote a record label while cropping a photo.
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I Used AI to Fight My Property Taxes
· 8 min readOn the last day to file, I used Claude Cowork between meetings to build our property tax grievance, from the rules and old emails to the form and exhibits. The part I kept for myself was checking every draft until it was right.
