Back in the 90s there was a series of infomercials in which a presenter named Susan Powter would shout “Stop the Insanity” right into the camera. If memory serves, she was railing about the insanity of diet regimens, or fad diets, or dieting followed by overeating, or maybe something else. But it was insanity, and she wanted you to stop. Here was this woman with arms like Popeye and a platinum white crew cut, and her shout was terrifying. But all I remember was the catch phrase. I’ve been uttering her catch phrase a lot lately, especially when it comes to my schedule.

Not that I am any busier than I have been in the past, it is the calendars that drive me insane. Here is the use case. I have three different personal boxes (a laptop, a desktop, and android phone). They share the same instance of Microsoft Outlook, which is fine for email but they each have their own calendar. The calendars are not synchronized or even shared. My first attempt at streamlining was to not use the calendar function on the phone. One box down with multiple boxes to go. Making matters worse, I have multiple email accounts that each have their own calendars. Add my work computer into the mix, and you can see trouble brewing. Why don’t you try Outlook for the web? Great question! For some reason, my desktop computer refuses to save meeting invites to Outlook for the web. Copying and pasting from the desktop to the web is messy at best. I still wind up missing webinars and meetings.

Can AI come to my rescue? Sorry. Not this time. I had a suggestion to try Notion because it can help organize calendars. Sure, you can add as many calendars as you like into Notion, but, alas, it only uses Google Calendar. So instead of stopping the insanity it injected more. There is also something called cal.com, but it is only for booking meetings with you (basically a freebie version of the free aspects of Calendly) rather than helping you keep track of meetings you’ve already booked. From what I can see, it appears to have its own calendar. AI-powered tools such as Perplexity, Lovable, and Replit are similarly disappointing.

There is no happy ending to this story. No magic tool to bring sanity to the world of multiple and incompatible calendars. To date my efforts at stopping the insanity have been futile at best.

I’m totally open to suggestions. What do you use to keep your calendars organized?