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1. To gain residency at my school, we have to do a RA next year. Now, or soon, is about when I should start looking for professors who may be interested.
2. I need to get letters of recommendation for some jobs.
3. I'm considering applying to transfer, and I need to speak with professors about their thoughts on this and gauging whether they would be willing to write a letter.

Awkward situation arises because it would seem like the professor(s) I would be speaking with about all these things would be the same. This isn't necessarily true, especially in regards to the RA position, but I feel like the letters would probably come from the same professor(s). However, the RA position adds another element, because I don't think I should really be looking for an RA position next year when I am also exploring transferring.

Any ideas on how to approach this whole situation? I feel like it is pretty weird, and probably not even doable, to ask a professor to write you a LOR for transferring, and then also saying I would be interested in a RA if I don't transfer. Almost as inappropriate is probably asking one professor for a LOR to transfer and another for a RA, since there is that chance I have to turn around and say, "Oh hey, can't do the RA. Peace."

One thing that may be worth considering is that part of my scholarship "guarantees" me a RA (because I am guaranteed resident tuition, which still requires working as a RA). So I feel maybe it is possible to wait until the last minute when I know I am not transferring and then being like, "Okay, I'm guaranteed a RA, so what do you have for me?"

Sorry this got long.

I mean, itf the RA position is really guaranteed no matter what this shouldn't be a problem. Also, you have more than 1 prof and I can only assume you need 1 letter of rec for the transfer. Ask one for a letter and ask another for an RA position.

You don't have to RA for a professor you've already taken, though that might be easiest. Why not ask to RA for professors that you know you want to take in the future if you stay at your school or, at the very least, professors who have backgrounds in career paths you're interested in? Then stick with asking for transfer LOR's from professors you've already taken.