I cannot overstate how fucking much I hate writing cover letters. It's been 15 years since I had to, and the situation has changed a lot since then...when I was right out of grad school, I was trying to make it look like I brought something unique when I felt like I was working with nothing (same could be said for my CV). Now, while I have lovingly crafted my CV into something that hits all its marks and is both compact and effective, cover letters are still just an ugly slog. I know what they need to cover and how to use them to frame up how the employer sees you, but they are excruciating to write, feel really stilted, and I feel like I can't find the balance between showing that I'm qualified, and coming of as been there/done that arrogant (and I'm occasionally trying to spin a ear of experience on something into being more impressive than I feel it actually is). There's a lot to be said and a very limited space to say it, and the whole thing just feels clumsy. I guess it's better to have the current problem with it than trying to make something out of nothing, but it is still obnoxious.
The other thing I find myself struggling with is figuring out how to access the "hidden" job market, where everything is done via executive search or by networks. I'm right at the edge of that, job-level wise. There are certainly some things I'm finding that are the right fit, but I know there have to be more out there, and I'm trying to figure out how to tap into those, or get the attention of the recruiters. There's got to be more than LinkedIn, right?