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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.
Don't forget to use tasks too. Spams your bosses task list with random stuff and reminders all the time.
Nice! I didn't know that!