However, the more years I've worked the more I have realized that I'm not really like that. I have tended to tell my bosses over the years the really big things. My divorce, my (subsequent) depressed time, my parents visiting and me having to take time to take care of them, my "I should leave academia", my "I'm going to look for a job since there's no promotion" and some other things. And I've come to appreciate the fact that I don't want to work for a boss that I don't trust, and that I can't feel respects me and want to support me.
It's probably mostly on how you tell these complicated things and what you share. I'm not talking about constant babbling about your personal things, this is more strategic opening up on specific things that might affect you in the work place and your boss having your back in case things get dicey. And most often, as a lot of things, these things are best to tell when you have a plan or know what you're going to do. Compare "they cheated on me with some young thing and I don't know what to do" to "my partner and I are going through a rough spot and I'm having a lot to process at the time". Not getting bogged down in details, but keeping the over all personal thing going.
I'm sure it helps that I work too much and pride myself of always being there for them when they need something. Flipside of that is, so far anyway, that they respect me and even support&help me find a new job "you're done with this phase of your life, let's find you a new thing and still keep in touch and want to promote me and my work". It's scary, don't let me tell you otherwise. It's very scary for me. I second-guess opening up every single time. I wonder the day after: "was it right, I told them this very private personal thing". And then I resign that there is nothing I can do anymore since the cat's out of the bag and you just have to move on.
The thing is though, that sometimes you can get some surprising insights and support. It's a trust-bonding exercise and so far *knock wood* it's been in my favour to have this trust with my bosses.
I'm not writing this out of the blue, obviously. I had one of those moments with my present boss. Now, this is the boss I know the least of so far. They play their cards very close to the vest as well. I'm not sure if it's based on something special, most likely because there is a division between personal life and work, and we mainly talk work. However, they have always indicated that if I wanted to enter personal space, they would respect and be mindful of it.
So, I did. It was very awkward. Don't get me wrong. I don't think I've been that scared and uncomfortable in many years. And then it came, the words that made me relax and accept that maybe, just maybe, my personal thing that I needed to tell them wasn't all that horrible or would make me a pariah or something. Maybe it would actually work out with them? The words were, of course, "Oh I remember when I went through this time X" and the very personal account came back, the sharing. Followed up by "what can I do", said with sincerity.
I understand that this is not something everyone can do with their bosses. And maybe I was mistaken in the trust and time will tell. However, I feel better now that I've let them see a part of my personal space, not to mention a lot better since I know a little more of their personal space. Just enough, not too much.
It's also worth remembering, that if you are going through something that has you leave work for check ups and stuff, it's most likely best to get out in front of it with your boss rather than hiding it. If nothing else, they can shield you from when your coworkers might get grumpy that you leave or aren't as available as before. You don't have to tell your boss the exact details but I'm in the camp "forewarned is better than ask forgiveness later"....
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