I'm terrified of confrontation - anyone else with me?

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I have worked with my current employer 10+ years and am at our maximum PTO accrual rate of 5 weeks/year. I've been looking at changing companies and have interviewed with a few. When I talk to HR, they often tell me the benefits package and note that I'd start, as a new employee, at the bottom rung of PTO accrual (often 2 weeks). Is this often negotiable? Is it unreasonable to think that the same years of experience that make me a good fit for a role should also qualify me for the higher PTO accrual rate? I realize I may not get all the way to where I am today, but to go from 5 to 2 is a kick in the gut.

Would this be appropriate, or should it be sent from a personal email account instead? Thank you in advance!

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My job has a lot of ebbs and flows. The busy season is almost upon us, but right now I have absolutely nothing to do. I am so bored all day long. When I'm bored like this, I usually start looking for new jobs. I have to be challenged to be content. But I really enjoy my boss, and I'm trying to stay here for at least another year or two. Last time I experienced down time, I subscribed to Coursera and got a certificate. Right now, I spend a lot of time on LinkedIn. I don't really have funds (personal or professional development through work) to do anything that has a significant cost. Does anyone have recommendations on what I should do?

I've been asking my manager for a new role for the past year, but they keep suggesting roles based on my past experience in a field I have no longer have any interest in and that I left almost 20 years ago. My resume shows years of experience taking on higher-level work, but my manager ignores that and keeps saying, "we need someone who can handle (let's say) data entry, and we know you are an expert!" Yes, I've handled data entry, but I did this work a very, very long time ago and have no desire to return to it. I'd rather management consider the interesting, much more challenging work I did right before they hired me a few years ago overseeing creative projects. How can I gently redirect them to my more recent experience that qualifies me for the higher-paying work I'd rather be considered for? I get it, the "need" someone to handle data entry, but find someone else as I already paid my dues and don't want to take on that work at this stage of my career? As a side note, I do feel that management is saving the better jobs for certain favorite staffers and pawning off the undesirable roles to others who were hired before the new regime took over.