Sooo many awesome suggestions here for you, OP!

One thing I don't think I've seen yet, is that you should create your calendar events as barebones as possible and then edit them to add each additional detail. This will notify everyone else attached of the updates to your event, every time you update any of them.

Don't add anything new to your calendar, just add them and they can see it's useless for the purpose they want. When they complain, mention the checkin system and that you need to be called. Or just a generic "School Visits" event that isn't specific to each location.

Make sure you have other evidence you're actually working. Make sure people see you at each location so you have witnesses if your boss complains.

What I don’t understand about this thread:

Each Gmail has its own calendar attached to it. My Phone’s calendar app supports multiple independent calendars displayed at the same time.

Why not use your work email to make a work calendar and a personal email to make a personal calendar? You can see both but your boss only sees the work one. That doesn’t seem unreasonable to me?

this must be a new thing. my old boss just posted on LinkedIn about keeping calendars visible for seemly no reason

I'd advise saturating him with an excessive amount of information. If he wants details, give him 10 times to many. Pollute every day with 50 status reports. Just keep on piling it on. If your boss decides to drive you crazy, then drive him even crazier.

Generate random events using AI and spam her.

Had to do similar for a micromanager that thought I was lying about my start times. He started calling asking where I was seemingly randomly. Then I saw him driving around one day in the lot swiveling his head around and realized he thought I was clocking in from home. (At the time I’d been occasionally parking about a mile away and hoofing it so my fat ass could get steps in before work. I explained this but he didn’t believe it).

So from then on if I didn’t feel like exercising I’d mark my arrival and hide my car somewhere in the lot behind trailers, a big dumpster, etc. and watch him drive around searching trying to catch me out. Then I’d see him find my car and shake his head. He knew what was up then. He stopped stalking my calendar and me after a couple days of that.

• Spam personal fake notes everywhere. "Joey's little league game", "Call dentist" and make completely useless ones like "remember the thing" for maximum annoyance.
• Add obscure religious holidays and random countries' national festivities. "Bhutan Losar day. Get decorations."
• Put in washed up celebrities' birthdays "David Hasselhoff's b-day".
• Include random bad album release anniversaries. "18 year release anniversary of Kid Rock - Live Trucker".
• Register inaccurate astrological milestones with random advice. "Leo ascending in Pluto. Good day for new beginnings".
• Every once in a while add events that are just random characters such as "HERDBhbcdbcnn nnnnnnnn" which you can later claim were added accidentally from your pocket.
• Make sure some of the events are written IN ALL CAPS
• Be lavish with your use of exclamation marks!!!!!1!!111
• Occasionally add reviews of your day scheduled for a few hours later as if using the calendar as a diary, including details about health conditions and sex life. "Rough day today.. had a lot of work and didn't want to get frisky because of the hemmorhoids"
• Write down random math calculations here and there that suggest you are confusing the calendar with an excel spreadsheet "=27.5/3"
• Include the most bland and sad motivational quotes every couple of days with several typos as if written ina rush: "YO cndo it!!!" "YOU WILL ALEAYS BE BEeeTIFUL, gril. Ownit!!!"
• Add fake Google search queries as if confusing the calendar with your search bar "cheap viernamese restaurant charlottesville" "how dolphins swim so fast ND jump"

Extra bonus points if you can invite him to the "events" and get the calendar to send him push notifications for occasional 5:30 am "wake up early for the thing". If he accuses you of bad faith for inviting him, tell him it's the default and you keep forgetting to remove him.

Not only will this annoy him, it will render the system impossible to supervise and you can always claim you ALWAYS organize your personals through your calendar and this "is just how i organize".

Good luck and give em hell.

Edit: Elaborated and more ideas

Edit 2: Few more ideas.

Add your driving to/from schools to the calendar, turn by turn

• 9:21 - Leave parking lot, turn to Capital Blvd and drive 420 ft
• 9:22 - Turn right towards Trawick Rd and drive 2.5 miles
• 9:27 - Turn left, enter parking lot

Resign, it will be better for both

Add a bunch of just normal things and then right in the middle:

10:45 - Rectal exam

The only one here so far not likely to immediately get you in trouble is the one about setting calendar reminders. By default, everyone with access to the event gets the alert with the event reminder.

Also, just being stupidly stringent with your time logging. 10:03-10:17 Gas, 8.9gal, $XX.XX to start pushing for (increased) mileage compensation.

Log every minute you go over time. It's a wonderful way to make managers twitchy.

Also, there are certain things you could reasonably expect them to want logged with this that legally they are not allowed to ask for. Not "Took a big fat steamer", what are you, 12? But "Bathroom" 1:10-1:15, and dare them to challenge it on the record. If they do, take it up the chain "I felt pressured to include this information in my time logs and now I'm being judged for it". That should raise alarm bells with anyone up above them.

Most of all, chill out. Just keep your shit in order and keep moving on. No reason to jeapordize your employment for pettiness.

Does your boss fish? If not, this might look disturbing to him.

Five Guys Hooker tournament 2-4. Entry: $75. Min length: 8". Biting = Big O

Fishing tournament sponsored by Five Guys from 2-4pm. Entry fee is $75. Any fish under 8" don't count towards total weight. "Big O" lure is expected to perform well.