"You're two drinks in and you're pitching a friend about what you want to do with your life. ... what do you have to lose being yourself?"

I think that's the real gem in your post. I've learned to really respect people are comfortable enough with themselves to be brutally honest. Even if that honesty isn't what I particularly want to hear.

I'd much rather see a resume from a "designer who gets slightly neurotic about misaligned pixels" or a "programmer who gets a rash when within 10 feet of complacency".