So here's my latest dilemma:

Fancy Private University -- FPU for short -- has just created and posted a brand new, very high level position that is potentially* my dream job. However, my immediate and longtime supervisor at FPU is not my biggest fan and isn't likely to strongly (if at all) support my candidacy. This wouldn't be such a big deal if my supervisor weren't viewed as a major rock star within the institution and if her boss, who pretty much knows only what my director tells her about me, weren't (A) very highly placed and influential in the organization and (2) directly reporting to the president, to whom this new position also reports.

Naturally, I intend to apply for the position. I am required, by FPU policy, to inform my supervisor of my application only at such time that an interview is scheduled, but there is nothing to prevent the person or team reviewing applications from mentioning my potential candidacy to my supervisor at any time, whether in passing or specifically to ask about my qualifications. So it seems like it would behoove me to tell my boss up front when I submit my cover letter and resume. Right? But then I'm more afraid that I won't get an interview at all. Although on further thought, I suppose that even if I get the interview, the odds of my ultimately getting the job aren't so great once they ask my boss what she thinks of me anyway. Hell, she could even be on the selection committee.

I am f**ked.

* I say "potentially" because it's not only a new position but an entirely new office and no information has been made available about how it will really work within the bigger FPU bureaucracy, whether there will be legitimate autonomy, and whether there will be support staff available to assist in making the whole thing viable.