Is it a good idea to go out with someone who doesn't want to be anything in life?

If they can hold down a good job than yes.

If they have a skill or a trade they can do very well without college. But if they're just planning on working some crap retail (or whatever) job for the rest of their life, that shows they have no ambition to go any further and that would bother me. I would want someone with the same aspirations in life that I have.

Yes

Good is subjective and may be relative to their family situations, how they were raised, who might have inspired them, or told them things negative. I think at the very least if you, or any have relationships that you consider worthy as friends, then perhaps you can inspire, or guide without preaching, to show them that they need not just SETTLE for what life may be.