Here, two things.
1. Normally I don't like to do too much good stuff for myself because I feel like if I get past a certain point bad things will happen. So it's easier to stay in the middle.
2. Relatedly, I don't like to schedule things. When I schedule things, nothing ever works. If I just do everything by feel, it seems to work nicely. Here is an example, so for work things, I don't schedule meetings, because the people will need to change it up a bit. Conversely, if I just show up and start talking to them, it seems to transpire. This drive my associates nuts, but it works for me. Totally, I would prefer the structure of having plans, but it won't happen, so why bother?
A separate way of looking at this is I am a control freak and when things don't go how I scheduled I get annoyed. Because I cannot have it exact, I don't want to give the effort at all.
This is the difficulty with which I am struggling. These things are starting to unhappily affect my life. I want to do things, but I believe if I do, perhaps I will reach some kind of tipping point where I get punished for doing too many good things for myself.
This has nothing to do with childhood. I had a wonderful childhood with kind, loving parents, during which I was generally supported and told I could do whatever I wanted. This is a new thing, sort of, learned through experience I guess. While I have some woo explanations for this, describe to me your summary first.