The first thing it scheduled was last year

This week from Katie

I wanted to start setting it up so badly. I just… couldn't start.

The Family Calendar Assistant was exactly the kind of thing I wanted: forward an email, have Claude parse through all the complicated (boring) details, and have the information land on the right calendar with the info I needed to know. Catey’s version was also going to require me to rework the carefully arranged calendar system I already had.

My system lived in Apple Calendar. Catey’s instructions were written for Google Calendar.

How would that work? Would I have to move everything? Would it still show up correctly on my phone? If I was going to bother setting this up, the system had to be PERFECT.

So I did nothing.

This is a classic cycle for me due to my ADHD. A task can be important, take 15 minutes, and something I actively want to do. None of that guarantees I’ll do it (just ask my husband).

Eventually, I texted Catey and Allie.

Her answer was to ask Claude.

This was a real revelation for me, and exactly right.

I told Claude that the guide assumed Google Calendar, but my entire life and carefully planned system was already in Apple Calendar. It explained that iCal wouldn’t work quite as well as gcal, throwing me into another stalled out attempt to get started. However, once I finally got over the hump, I found that Google could sit underneath because that was what Claude could best connect to, with iCal as the screen I actually used.

The instructions didn’t fit my situation. With the help of Catey, Allie, and Claude, I was able to adjust it to what works best for me. I still hate google calendar, but the system works with it as the base.

The first time I used it, it didn’t seem to work —* I couldn’t find my daughter’s swim classes anywhere. After working it through with Claude, I eventually located them. In 2025.

But now it works. I recently sent along 3 different PDFs of instructions for my daughter’s 4 hour allergist appointment. It parsed the instructions, told me what I needed to know and created a packing list.

*This em dash was included by Katie, on purpose.

What actually helped

01 Ask AI to adapt the instructions

A guide does not have to match your exact tools to be useful. Tell AI what the instructions assume, what you actually use, and ask it to explain what needs to change.

This is also much easier than trying to understand every technical implication before you begin. I know because I tried the other approach first.

02 Treat the first failure as part of the setup

A new system often makes you slower before it makes you faster. You spend time learning the tool, and correcting the first bad result while the old system is still running in your head.

Swim classes in 2025 was the dip.

The allergist appointment was the beginning of the climb.

03 Make the task interesting enough to start

AI does not fix my executive dysfunction. It can make an otherwise boring or intimidating task more interesting.

Instead of “rebuild the family calendar,” I had a specific problem to solve: how can I keep using Apple Calendar while connecting the system through Google? That question was new. Learning the answer was interesting. Once I was moving, I could keep going.

Sometimes I don’t need the whole task to become easier. I need an entry point that makes me curious enough to begin.

Tested in Real Households ✓

The party plan started on paper

Before I opened Notion, I drew the dashboard I wanted on a piece of paper.

I photographed the pages, uploaded them to Notion AI, and asked it to turn what I had drawn into a working dashboard for my daughter’s first birthday party.

It gave me one place to plan the budget and keep track of the many details involved in a first birthday party, including the contents of the gift bags. I do not have strong natural feelings about the contents of gift bags for 1-year olds. They still have to contain something.

The prompt

“I’m uploading photos of a dashboard I drew on paper for my daughter’s first birthday party. Use my layout and notes to build a Notion dashboard where I can track the budget, tasks, purchases, decisions, and anything that still needs follow-up. Keep the structure simple enough that I’ll actually use it. Before building, tell me what you think each section of my drawing is meant to do and ask about anything that isn’t clear.”

The honest verdict

Notion did not make me care more about gift bags. It made planning the party more interesting because I was learning a new skill while I did it.

That novelty was enough to get me started. Once the dashboard existed, the structure helped me stay organized and moving. The budget became much easier to manage, and the small details had somewhere to live besides my head.

The party still required planning. I was just finally willing to do it, and once I did it took one hour instead of five.