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I have a 3.9 GPA from a top public university that I transferred to after two years of community college.
I scored a 157 on the December LSAT and plan on retaking in June.
I am not a URM.
I have been working full time in bars/restaurants since I was 16 (I'm 25) and so while I have a ton of WE- it's not exactly relevant which I'm afraid may hurt me. I also have a GED and I'm not sure how that's going to effect my chances. I'm also not sure how much I should address that issue in my apps.

I am retaking the LSAT because I have my heart set on a t14 school or at least some $$$$.

I'm looking for some folks to agree with me that I should retake in June rather than Feb or any advice you may have.

If your heart is set on T14, definte retake and study you a$$ off. Just wait until June to give yourself the best shot, because either way you'll have to apply next cycle. Your GPA is gold, but for T14 Admit you need to hit at least 164 to put you in consideration. If you can hit 168+, $$ starts to enter the picture in the lower T14.

*Also, your work experience should still count for something even if it isn't professional. Stress things like what you learned, how it matured you, how you balanced work and school, any promotions/responsibility increases, etc...

don't waste that gpa -- retake