While I'm generally the type of guy who is "all in or nothing type", why not start this off slow. This is a radically different system and with all things drastic, it'll take time to get used to.
Why not try something like carrying and making purchases with the CC for the first week of each month, then automate payments to that card in the beginning of the next week. Do this for about 90 days ( which is recommended for developing new habits). Once you've succeeded, why not increase that to two weeks of the month, and so on.
This is the Personal Development topic after all, so I definitely agree that you should push yourself and try and build your discipline. That is the point of life, to grow. I think, if you implement a system where you slowly ease into a new habit, it might prove effective. This is somewhat like the debt snowball method where you try and conquer, small and immediate victories. The more you do it, the more your confidence will develop. And before you know it, you'll be carrying that CC around for whole months, and still maintaining your frugal lifestyle! Imagine that. It always begins with single small steps.