I got this question from watching Bob Proctor's "Born Rich" program, and it had a profound effect on me.
There are twin polarities in achievement: Success and Failure.
If you are more motivated by escaping failure (i.e., paying your rent on time, not getting fired, paying off your credit card debt), then that's all you'll get.
Resisting the worst-case scenario will always keep you just a few steps away from that scary place.
You need to make your Success Polarity stronger. You have to truly love the wealthy lifestyle, which can be difficult if you haven't experienced it. This is where Bob Proctor's stuff and Psycho-Cybernetics helps a lot.
I've thought of other variations of this question.
"Do I love being with friends more than I hate loneliness?"
"Do I love being in good shape more than I hate being out of shape or fat?"
"Do I love romance more than I hate not having a romantic partner?"
See where you lie on each scale of polarity. You may find that the places of your life you're most lacking in have you in the most "defensive" mindset.