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From day one I stated than I do not carry my phone with me. When I am home, the phone is charging in another room and I don't look at it until morning or when I'm ready to go to bed. On weekends, I don't carry it at all when I'm with my husband. I've also had to remind the boss that I am in the office earlier than everyone else - they get in around 11 and I'm here at 8:30. I need to leave at the end of my scheduled hours as this is the only time I am able to take care of items at home. I think they sometimes forget that us little folk don't have "people" to take care of things for us and we also don't have the freedom to come and go from the office during the workday as they do.
I just don’t answer anything outside of working hours, period, and don’t follow up until I’m back on the clock. I also don’t check emails or my work phone unless I’m on the clock, aside from the occasional exception where it benefits me. Unless being on call was part of the agreed expectation when you signed on, there’s no reason you should be keeping up with work on your personal time.
More often than not it’s our actions that teach people how to respect our boundaries, not what we say. Have the conversation letting them know you’re no longer checking outside of agreed hours, but then back that up by not being available.
Can you dedicate a specific person for him to reach out to you while you're gone? Even if that means hiring a temporary assistant? What he's doing is entirely inappropriate, but he may not know where to go with important questions when you're away.
That’s a good idea for vacation/sick time. If there’s another assistant at your office, I’d definitely see if they’re able to cover and I’d offer to do the same for them next time they’re out.
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Some people just have an inflated sense of self. Nothing you do will probably change what they are doing. Set those hard boundaries and stick to them. If you're OOO, don't check your email. When you get back, respond to the email and say that as discussed on XX date, I was OOO. If something still needs to be done, then I'd take care of it. I'd just be sure to have all time off communicated in writing so they can't claim they knew nothing about it.
When starting a new job, I’m always up front that I put in 100% when i’m on the clock but don’t have email on my phone or check it from home. My attorneys know that if it’s truly urgent they can call me or text me and i’ll log on. It sounds like a boundary needs to be established here. Remind him that you won’t be available during off hours, and then stick to it. Unfortunately if you keep checking email and taking his calls, he thinks he can continue doing it.
If someone is out sick or out on time off, that is their time to recover or etc. hence they are not working unless the employer wants to pay them for that extra time being put in. Have you informed your Human Resources? If you end up in the hospital, does he expect you to answer your emails and give him a call? I would look for something else and in a place that will respect you more as both a person and an employee. If you still have the emails I would save them and also any call logs on when you called him or he called your cell when you were not actually working because then you can actually legally go after him and also HR if you have informed them and the behavior has not stopped.