A few weeks ago I decided to try an experiment: hand everything off to AI. Calendar, meals, work schedule, daily journaling prompts — all of it. Not because I thought AI would be perfect at it, but because I wanted to know exactly where it helps and where it doesn't.
Here's the honest account.
What I Actually Did
I started on a Sunday. I dumped everything I needed to get done in April into Claude — work projects, personal commitments, fitness goals, social obligations, a few things I'd been putting off for weeks. Then I asked it to build me a monthly plan.
Not just a calendar. A system. When to do focused work. When to batch errands. When to leave buffer for the unexpected. I gave it my working hours, my energy patterns (morning person, slower after 3pm), and a rough sense of which projects were highest priority.
It gave me back a plan. Surprisingly good. Organized by week, with themes — a "heavy writing" week, a "catch-up and admin" week, a week with more space carved in because I'd mentioned a friend visiting.
What Actually Worked
Calendar blocking. This was the clearest win. AI is genuinely good at looking at a list of obligations and suggesting how to distribute them. It's better than I am at not overloading Tuesday just because Tuesday is the most obvious day. It spread things evenly in a way I almost never do manually, and it respected my stated energy patterns.
Meal planning. I told it I wanted to eat well, I don't want to spend more than 30 minutes cooking on weeknights, and I had a few things I can't eat. It gave me a week of dinners with a shopping list organized by section of the grocery store. I did this for four weeks in a row. It worked. I spent less time standing in front of the fridge making bad decisions.
Journaling prompts. I asked for a daily prompt for each day of the month — something that would push me to actually reflect rather than just write "had a good day." These were genuinely good. Not generic ("what are you grateful for?"), but varied and specific. Some were uncomfortable in the right way. I didn't use all 30, but I used most of them.
Reviewing decisions out loud. A few times I used AI like a sounding board — I had a decision I was sitting with, I described the situation, and I asked it to help me think through it. This worked better than I expected. Not because it made the decision for me, but because having to explain it clearly enough for AI to understand forced me to articulate what I actually knew and what I was avoiding.
What Didn't Work (Or Felt Weird)
It doesn't know what a Tuesday actually feels like. The plan was technically sound. But AI has no sense of the particular kind of tired you feel after back-to-back video calls, or the fact that Thursday afternoons at my desk have a different texture than Thursday mornings. I ended up adjusting things mid-week more than I expected — not because the plan was wrong, but because life is granular in ways a calendar can't capture.
Over-optimization. The first draft had me scheduled pretty solidly. It was a lot. I had to explicitly push back and ask it to build in blank space — time that wasn't for anything. It's not intuitive to AI that unscheduled time has value. You have to name it.
Accountability doesn't come with the plan. The plan was good. Following it was still on me. I assumed — without quite saying so — that having a plan from AI would somehow make it easier to stick to. It didn't. A plan from AI is just a plan. What makes you follow through on it hasn't changed.
Journaling felt slightly clinical. A few of the prompts were great. Some felt like they were generated by someone who'd read a lot of journaling content but hadn't actually journaled. They were technically correct prompts — and I'd rather have those than none — but occasionally I'd read one and just swap it for my own question.
What I'll Keep Doing
The grocery list and meal planning, without question. That's now a permanent part of my Sunday routine. Twenty minutes of prompting saves me hours of decision fatigue across the week.
Calendar blocking for heavy weeks. Whenever I have a lot coming in, I'll run it through AI before I schedule it manually. The spread is better and I'm less likely to accidentally make one day brutal.
Using AI as a thinking-out-loud partner when I'm stuck on a decision. This is underrated.
The Honest Summary
AI is an excellent planner and a terrible accountability partner. It can see the whole month at once and suggest a sensible shape for it. It cannot feel the week with you, understand when you're running on empty, or notice when you've quietly stopped following the plan.
Use it to build the structure. Then show up for it yourself.
Next week: a blunt look at why most AI agents are significantly less impressive than the demos suggest.
