Now, this is where the fun bit comes in. Pay attention to how your brain just successfully defended you against changing your assumptions.
Specifically, the assumption that your parents need to be proud of something... when, in fact, normal healthy parents are proud of their kids when they make mudpies or say "gaga" or something.
To put it another way, your brain has habituated to assuming that your parents' pride is supposed to be conditional on you doing something, and that it's therefore somehow "not right" for you to feel pride in yourself, unless you're doing something that would get your parents to be proud of you.
This is the way SASS imprinting works -- we pay attention to what our parents and peers give us positive and negative SASS for, and then we internalize the algorithms we observe them using, for when to give ourselves (and other people) positive or negative SASS.
This is how we acquire our (effective) value systems, and the way to undo it is by changing the rules under which our self-supplied SASS pellets and shocks are delivered.
Part of doing this is just realizing that it's really you who controls your own SASS allocation. Just now, by me asking you how you'd feel if your parents were proud of you, you began to feel some of the relief that you'd feel if you increased your self-delivered level of Status. (Specifically, in the "pride" part.)
Of course, as discussed elsewhere in this thread, you stopped imagining as soon as you found an objection to the experience.
Notice how you then quickly changed what you were imagining to restore your previous world model -- you were to imagine what would happen if your parents had unconditional pride in you, and you immediately began asking, "but what do they have to be proud of?"
And the reason you're "feeling confused" is because I just asked a question that draws on your brain's information in a way that leads to a contradiction in your current mental model... similar to the confusion a theist feels when an atheist argument hits too close to home.
The response is also similar: defend the existing belief structure by treating the original belief as axiomatic... and the rest of what you wrote is, as you said, "rambling"... a successful distraction to get you away from even temporarily accepting a premise that would annihilate a chunk of your current worldview.
One of the reasons this sort of thing is difficult is because children are wired to believe their parents are intrinsically perfect, and that therefore any negative consequences of interacting with parents are considered to be your fault. If your parents aren't proud of you (giving you Status pellets), then you must be defective.
Of course, later on in life, we do gain the ability to criticize our parents, their values and behaviors. But by that point, the damage is already done: we've already adopted their rules for SASS allocation, tucked away out of conscious awareness. And thus, we rarely question them.
Now, the questions I've asked you are part of the process of pulling your imprinted SASS allocation rules into the light, where they can be destroyed by reflection. They don't work, however, if you back away from the question. Your desire to experience something new -- to learn more of the truth, if you will -- has to exceed your desire to remain comfortably within your existing world view.
If you repeat the question -- and this time, actually allow yourself to experience what it would be like if your parents had always been proud of you... then a portion of your current worldview will die, but YOU will become more free.
And that's because your current SASS rules are over-constrained compared to a normal, healthy human being -- one who knows in the back of their mind that their parents were always proud of them, always loved them... and thus has set their internal Status and Affiliation setpoints to a higher minimum setting than yours.
So, if you've ever wondered what the difference was between you and those other people, now you know. And you also have a piece of what you need to know to DO something about it.
The rest is really up to you.
I don't normally do the sort of thing I've been doing with you, with people who aren't paying me money to do so. But that's not as much a matter of needing to make a living, as it has to do with the fact that people who haven't put something important on the line in order to get my advice, aren't usually that motivated to stick with it through their resistance to the actual process of changing.
When somebody's paying me money, though, they implicitly grant me a role and a degree of Status in their mind that facilitates their complying with my instructions, even when it's difficult. It also allows me to hand them back some of that Status, through my paying attention to what they're saying, and showing persistence in sticking with the interaction myself, even if it's as difficult for me as it is for them.
(This same sort of transaction also occurs in therapy, coaching, and other paid interactions between human beings, btw. Because by default, we assume that at least our Status and Affiliation have to come from other people. The irony, however, is that the people who really have SASS in their lives are the ones who learned good rulesets from their parents for when to give themselves (and others) positive SASS.)
Anyway, now I'm rambling, too. ;-)
What does SASS stand for?
Note: this post is basically just summarizing some of PJ Eby's freely available writings on the topic of pain/gain motivation and presenting them in a form that's easier for the LW crowd to digest. I claim no credit for the ideas presented here, other than the credit for summarizing them.
EDIT: Note also Eby's comments and corrections to my summary at this comment.
Eby proposes that we have two different forms of motivation: positive ("gain") motivation, which drives us to do things, and negative ("pain") motivation, which drives us to avoid things. Negative motivation is a major source of akrasia and is mostly harmful for getting anything done. However, sufficiently large amounts of negative motivation can momentarily push us to do things, which frequently causes people to confuse the two.
To understand the function of negative motivation, first consider the example of having climbed to a tree to avoid a predator. There's not much you can do other than wait and hope the predator goes away, and if you move around, you risk falling out of the tree. So your brain gets flooded with signals that suppress activity and tell it to keep your body still. It is only if the predator ends up climbing up the tree that the danger becomes so acute that you're instead pushed to flee.
What does this have to do with modern-day akrasia? Back in the tribal environment, elicting the disfavor of the tribe could be a death sentence. Be cast out by the tribe, and you likely wouldn't live for long. One way to elict disfavor is to be unmasked as incompetent in some important matter, and a way to avoid such an unmasking is to simply avoid doing anything where to consequences of failure would be severe.
You might see why this would cause problems. Sometimes, when the pain level of not having done a task grows too high - like just before a deadline - it'll push you to do it. But this fools people into thinking that negative consequences alone will be a motivator, so they try to psyche themselves up by thinking about how bad it would be to fail. In truth, this is only making things worse, as an increased chance of failure will increase the negative motivation that's going on.
Negative motivation is also a reason why we might discover a productivity or self-help technique, find it useful, and then after a few successful tries stop using it - seemingly for no reason. Eby uses the terms "naturally motivated person" and "naturally struggling person" to refer to people that are more driven by positive motivation and more driven by negative motivation, respectively. For naturally struggling people, the main motivation for behavior is the need to get away from bad things. If you give them a productivity or self-help technique, they might apply it to get rid of their largest problems... and then, when the biggest source of pain is gone, they momentarily don't have anything major to flee from, so they lose their motivation to apply the technique. To keep using the technique, they'd need to have positive motivation that'd make them want to do things instead of just not wanting to do things.
In contrast to negative motivation, positive motivation is basically just doing things because you find them fun. Watching movies, playing video games, whatever. When you're in a state of positive motivation, you're trying to gain things, obtain new resources or experiences. You're entirely focused on the gain, instead of the pain. If you're playing a video game, you know that no matter how badly you lose in the game, the negative consequences are all contained in the game and don't reach to the real world. That helps your brain stay in gain mode. But if a survival override kicks in, the negative motivation will overwhelm the positive and take away much of the pleasure involved. This is a likely reason for why a hobby can stop being fun once you're doing it for a living - it stops being a simple "gain" activity with no negative consequences even if you fail, and instead becomes mixed with "pain" signals.
So how come some important situations don't push us into a state of negative motivation, even though failure might have disastrous consequences? "Naturally motivated" people rarely stop to think about the bad consequences of whatever they're doing, being too focused on what they have to gain. If they meet setbacks, they'll bounce back much faster than "naturally struggling" people. What causes the difference?
Part of the difference is probably inborn brain chemistry. Another major part, though, is your previous experiences. The emotional systems driving our behavior don't ultimately do very complex reasoning. Much of what they do is simply cache lookups. Does this experience resemble one that led to negative consequences in the past? Activate survival overrides! Since negative motivation will suppress positive motivation, it can be easier to end up in a negative state than a positive one. Furthermore, the experiences we have also shape our thought processes in general. If, early on in your life, you do things in "gain" mode that end up having traumatic consequences, you learn to avoid the "gain" mode in general. You become a "naturally struggling" person, one who will view everything through a pessimistic lens, and expect failure in every turn. You literally only perceive the bad sides in everything. A "naturally motivated" person, on the other hand, will primarily only perceive the good sides. (Needless to say, these are the endpoints in a spectrum, so it's not like you're either 100% struggling or 100% successful.)
Another of Eby's theses is that negative motivation is, for the most part, impossible to overcome via willpower. Consider the function of negative motivation as a global signal that prevents us from doing things that seem too dangerous. If we could just use willpower to override the signal at any time, that would result in a lot of people being eaten by predators and being cast out of the tribe. In order to work, a drive that blocks behavior needs to actually consistently block behavior. Therefore attempts to overcome procrastination or akrasia via willpower expenditure are fundamentally misguided. We should instead be trying to remove whatever negative motivation it is that holds us back, for otherwise we are not addressing the real root of the problem. On the other hand, if we succeed in removing the negative motivation and replacing it with positive motivation, we can make any experience as fun and enjoyable as playing a video game. (If you haven't already, do check out Eby's Instant Irresistible Motivation video for learning how to create positive motivation.)