Anyone who cares for school-age children has probably dealt with the nightmare that is the school calendar. School calendars are often formatted as PDFs, images, or Word documents that are often very mobile-unfriendly. Finding the calendar on the school website or in emails (why do schools send everything as an attachment?! Ugh!) is a nightmare when you need to find out if your child has school on Presidents Day.
If you've never been dumbfounded when your child tells you they have a half day off today, I salute you, while the rest of us sweat and scramble to expend 30% of our brain cells trying to juggle the school calendar with the calendar of after-school activities, deal with the myriad of forms that need to be filled out, and make sure that yellow shirt gets washed before Color Day for Spirit Week (a task that, of course, is often done by moms).
I understand that public schools are schools for education, not for web design — hard-to-use calendar formats and website revamps are not a top funding priority — so I'm going to roll up my sleeves and do it myself.
Well, yeah, I'd love to see an AI do this.
Last week, I was inspired by Dan Seifert, a former reporter for The Verge and now a Googler, who posted on Threads about how he used AI to take a Word document with his child's school calendar on it and pull the dates into his Google Calendar in just a few clicks.
For me, this was a dream come true.
Seifert explained how he did this using a Google Pixel smartphone. I reached out to Seifert but he wasn't authorized to discuss the details publicly. I don't have a Pixel so I wasn't able to adapt his method exactly, but I'm grateful for his inspiration.
After about 2 hours, 3 LLMs (ChatGPT, Gemini, Claude), and a lot of frustration, I finally got this to work. To test further, I tried this method on two other friends and their school calendars and found it worked for them too. It took some tweaking to deal with the oddly formatted calendar, but it still worked. Victory!
I suffered, so I am happy to tell you how I overcame it so that you don’t have to suffer and so that you can do the same.
A few things to note:
I'm by no means an AI guru, so there may be a better way to do this. If you have any suggestions for streamlining, I'd love to hear them. I was using the free versions of these LLMs, but it's possible that the more powerful paid versions could do this better.
My steps are as follows:
Step 1: Get your school calendar. This can be a PDF, a screenshot of the calendar, or even just copying and pasting all the text from a written document.
Step 2. Use ChatGPT to read the PDF or image and convert it to plain text.
Prompt: “I have a PDF of a school calendar with a list of dates. Please convert this PDF into a text list of all the dates and their descriptions.”
Step 2. Convert that plain text into a CSV file suitable for Google Calendar. It may take a few tries to get it in a format that fits Google Calendar exactly. You may need to require the date to be first.
Prompt: “Can you convert that list into a CSV file with dates in YYYY-MM-DD format that can be imported into Google Calendar?”
Step 3. Download the .txt version provided or copy and paste it into a text editor.
Tip: I found Claude.ai to be better than ChatGPT and Gemini for this step, as Claude also creates a downloadable version, saving me the trouble of pasting and saving it myself.
Step 4. In Google Calendar, create a new calendar using the + sign next to “Other Calendars” (it's in the left rail if you're on desktop). Give it a name, like “School Calendar.”
Tip: Share it with your partner so they can't claim they didn't know that some random Tuesday was a “Teacher Development Day” holiday.
Step 5. Import the .txt file into Google Calendar. Go to Settings > Import and Export > Import. Upload the file from your computer and select the calendar you want to import it into. If you get an error message or it says 0 events were added, you'll need to go back to step 2 and adjust the format again.
Step 6. Triple check what you entered into GCal against the original data, there might be some glitches that prevented it from working perfectly.
Step 7. Feel good about yourself for being an efficiency master. Congratulations!
What you need to know
This wasn't as easy as I expected – it took a bit of trial and error, and some LLMs couldn't do all the steps on their own, which of course was very frustrating.
For some reason, Gemini was the worst of them all in terms of being able to do this, and also oddly gave incorrect information about how to use Google products – for example, it initially said you could read PDFs in Google Drive, but later said you weren't allowed to access files in Google Drive.
Also, when I asked how to add all these dates to Google Calendar, instead of telling me how to import the file, I got the wrong instructions (suggesting I create a single event and put all the plain text in the description). I thought Google's Gemini would be great at supporting other Google products, but that's not the case.
I imagine Google (and other companies) will make this workflow much easier soon. This seems like an ideal use of AI as a productivity tool: “I have a document in Gmail or Drive with a list of dates. Add all of those dates to my calendar.” That's the kind of magic we'd expect from AI.
And indeed, there are companies working specifically to help families handle this tedious task of calendar management: Ohai, an app for moms that acts as an assistant to help with calendar management and other tasks (it costs $27 a month and sounds promising, but I haven't tried it yet).
There's also the Skylight Calendar, a $300 digital calendar touch-screen device (with a larger wall-mounted version coming this fall for $600). My editor Hayley Peterson bought one for her family and says they love it.
But I have a feeling that by the time the next school year rolls around, all this hassle will be irrelevant: With the new Apple Intelligence in the new iPhones and other more powerful AI models, I think all of this will be as easy as a few taps on your phone, no more hassle importing .txt files (shudder).
I know some people worry that AI will take our jobs, overwhelm us with misinformation, and harm us in ways we haven't yet predicted. I worry too. I don't use AI much at work (I wrote all of those words with my own two fingers), but I'm really happy that this tool is actually making my life a little better in these small ways.
