A psychologist or counsellor would tell you that your problem is pretty normal. The machinations of money are very rational and rigid as computer code. Personal Finance is only 25% rational financial knowledge, the other 75% is all about behavior management. You seem to have the motivation for and rational knowledge of Personal finance and you identified the problem...it is your psychology. One of the major psychological barriers to rational money management is age. Human capacity to think logically especially about money matters does not really start maturing until age 35 and crescendos in the 50s. Until then you are preoccupied with a lot of primal motivations such as food, status, attention and sex,sex,sex. Failure is quickly removed from conscious acknowledgement as humans are hardwired with 106 cognitive biases to rationalize such failures especially when the come to status and money. One of the rationalizations is that "I just don't want to hear a bunch of psychological mumbo jumbo about my money". You look like you are starting to approach the rational thinking demographic so get ready...things will start to fall into place shortly.

Human nature is a tough thing to break. Which is why I resort to trickery.

All of my finances, except for buying groceries and the like, are entirely automated. Making changes in any of my system involves delays of up to a month, and I know this. After doing my budget out, I figured out exactly how much I need to cover expenses, plus a little extra (about $25). Everything else goes into the 401k/IRA, and an emergency fund that is very annoying to access.

Result? I have tricked myself into paying all of my bills on time, investing in my future, saving for emergencies, and feeding myself, all without really having to think about it. At the same time, when I want something, I have no option but to save and scrimp in areas of my working budget to afford it. It's as if I have tricked myself into believing the other money does not exist.