AI PM 
Parenting 
Automation 
Claude 
My kid is smart. I know that because his teachers tell me, and because I can see it in the quality of the ideas he produces when he actually does the work.
Smart-kid problem: when a kid can get away with doing minimal work and still do well in school, they don’t develop the habits and skills they need for when the going gets tough. We’ve all seen this (or in my case done it). You do great until 11th grade, 12th grade, sometimes it takes until college, and then your old approach stops working and you’re left scrambling. With no idea what “good” looks like.
Sound familiar?
I spent months trying different approaches. Reminder apps. Parent-reviewed planners. Weekly check-ins. All of them shared the same flaw. They required the student to plan their own week, but exactly what is that plan supposed to look like? There are lots of tips and examples out there, but in the age of AI plus schools that publish assignment calendars, it occurred to me that we have access to the best practices and the real-time data we need.
Let Claude do the grunt work of planning. And, more importantly, let it teach my kid what it actually means to be a good student.
So we built something different.
What Study Buddy is
Study Buddy is an automated weekly task generator. Every Sunday at 6 PM, it reads my son’s school assignment calendar, figures out what’s due in the coming week, and pushes a structured, time-stamped task list to a shared TickTick list.
It’s not just a copy of the assignment calendar. The skill creates and schedules the specific tasks needed for the type of assignment. Tests get three tasks, one for each day leading up to the test. The first is overall review and identifying weak spots. The second is targeted studying. The third is a day-of review. Essays get five: outline, evidence, draft, revise, submit. One stage per evening.
He wakes up Monday morning and his week is already planned. Not by me. I didn’t touch it. By a system that read his calendar, classified each assignment, figured out how many steps it needs, calculated when each step should happen based on his actual schedule (including lacrosse practice, lacrosse games, and yes, Bruins game nights), and generated specific tasks with help text for each one.
He doesn’t interact with the automation at all. He just uses TickTick.
Why this approach
The bottleneck isn’t motivation. It’s planning.
Most students don’t cram because they’re lazy. They cram because they never translated “test on Thursday” into “study Tuesday, study Wednesday, quick review Thursday morning.” That translation requires executive function, foresight, and time estimation. Skills that are genuinely hard for a lot of teenagers and that get harder as the workload scales.
Study Buddy does that translation automatically. The student’s job is to do the work, not to figure out what the work should be.
How it works
The system is a Python script that runs on a Sunday-evening schedule. The flow:
1. Read the calendar. The school publishes an iCal feed with all assignments. The script fetches it fresh every Sunday and parses every assignment for the coming week.
2. Classify each assignment. A quiz, a test, an essay, a reading, a project. Each gets handled differently. A test generates three tasks spread over three days. An essay generates five tasks covering brainstorm, evidence, draft, revision, and final submission. A long-term project generates milestone placeholders with a checklist the student fills in to match the actual scope.
3. Check the schedule. Lacrosse practices and games shift task times to accommodate the real day. If there’s a Bruins game starting before 7 PM, all tasks are moved earlier so homework gets done before puck drop. (Yes, I know how this sounds. He’s a teenager. I’m picking my battles.)
4. Add standing tasks. Regardless of what’s assigned, a short Hebrew vocabulary review and a quick Algebra practice set appear every evening. Ten minutes each. The kind of low-investment, high-return habits that compound over a semester.
5. Push to TickTick. The full task list, with specific times, subject tags, and help text, is pushed to a shared TickTick list in a single batch. The student sees it when they open the app.
6. Follow up on weak spots. Every task ends with a brief self-assessment prompt. The student rates their understanding from 1 to 5. If they score a 3 or below, a new task is automatically created the following week: “Book office hours with [teacher].” It shows up in their list, due Friday, so they actually do it before the confusion compounds.
What the student experiences
He opens TickTick on Sunday night or Monday morning and sees tasks for the whole week. Each task has a specific time. Not “do this sometime Tuesday,” but “Tuesday at 7:30 PM.” Each task has two or three bullet points telling him exactly what to do. Not just “study for the test” but “identify your weak areas in this unit, work practice problems on those specific topics, flag anything you still don’t understand.”
At the end of each task he answers one question and gives himself a score. The score is private. It’s not reported back to me automatically. It feeds the carry-forward logic. It’s a habit of honest self-assessment, which is arguably more valuable long-term than any individual study session.
He can reschedule anything in TickTick. He can mark tasks complete whenever they’re done. The system adapts the following Sunday based on what the school calendar says, not based on his behavior last week.
What I experience as a parent
I don’t touch the task list. I don’t build his week. I don’t remind him to look at the calendar. The Sunday run happens automatically. I get a notification when it completes.
What I do is occasionally look at the TickTick list (we share it) to see what’s on his plate and whether things are getting done. The system gives me visibility without requiring me to be the planner or the nag.
The office hours trigger means low-confidence moments get surfaced automatically rather than buried. I don’t need to quiz him after every test to find out if he understood the material.
What it doesn’t do
I want to be clear about what this system doesn’t do.
It doesn’t make a disengaged student engaged. It doesn’t replace the conversations about why school matters, or the harder work of figuring out what a student actually needs. It doesn’t catch everything. If a teacher posts an assignment late or with an unusual title, it might not appear in the task list.
What it does is show a student a concrete, tangible example of how to be good at learning in a traditional school environment without the burden of planning on top of the habit change.
It’s also a useful example for him of how he should be using AI at school, and the kinds of capabilities worth exploring and learning more about.
The technical bit
The whole thing is about 800 lines of Python that runs in under 10 seconds. Stack:
- Python script with
icalendarandpytzfor parsing the school calendar feed - NHL public API for the Bruins schedule (no API key required)
- TickTick MCP for pushing tasks
- A scheduled run for the weekly automation (Sunday 6 PM)
The configuration lives in a single file. To adapt it for a different student, you change the iCal URL, the TickTick project ID, the subject names, and the teacher list. That’s it. The repo is here: github.com/squidstein/study-buddy. Setup walkthrough is in docs/setup-guide.md.
So far
So far, it’s working.
He’s doing the work. He’s not asking me when to do it. He’s not getting blindsided by tests. The office hours follow-ups have happened a handful of times and one of them genuinely caught a misunderstanding before it compounded.
What I’m watching for is whether the underlying habit transfers. Whether the version of him that’s been operated on by this system for two semesters internalizes the pattern enough to keep doing it without the scaffolding. That’s the real test, and it’s a year or two away. The system is the training wheels, not the bike.
If you’ve built something similar, or if you’re trying to and getting stuck, tell me about it. The skill page is here: Study Buddy.