Punishing yourself, make yourself feel guilty etc.

Actually, you do not understand why you do this to yourself, this punishing. You talk yourself into a guilt trip, there are many things 'wrong' about you, etc. And yet, seen from the perspective of your personality, this is a logical mechanism, as you may read here:

In a given situation, your personality repeats the well-known mechanism: perception > judging/interpreting > feeling pleasant/unpleasant > hold on to feeling (when pleasant) or get rid of it (when unpleasant). Punishing yourself is one of the mechanisms to get rid of a feeling and upholding the idea that the outcome of your personality interpretation could have been a more pleasant one if only ...

A practical example: you perceive that someone says something to you, you judge this to be offensive, the feeling which results from this interpretation is an unpleasant one, and now you have to get rid of this feeling. Your personality prefers to do so through blaming somebody else, however, often enough he does not succeed or succeed completely here in order to be able to get rid of the feeling. So now he still faces a (rest) of unpleasantness.

Normally he would want to punish somebody élse for this, through making this person feel so uncomfortable that he would never attempt this once more, and thus he believes to have prevented you from having to go through an experience like this once again, simply because this person would no longer attempt to give you the input for it. And it allows your personality to uphold his own standards and ideas.
When there are not enough possibilities to effectively project the blame onto others (for example because you believe the other is more powerful, or more right, has more insight or simply because there is nobody else involved), he uses you yourself to act out the same mechanism. And according to this mechanism he states that when yóu would feel bad enough, you would not attempt to repeat a thing like this once again. And 'so' he once again was able to preserve the idea that a pleasant outcome according to his standards still remains possible.

Now you experience a problem within yourself, since on the one hand you did what you did because it seemed to turn out 'good' according to your personalities' standards. Then you were overruled by your practical experience afterwards and this outcome turned out to be not guaranteed. Now your personality states that you would have to have done something élse, and at the same time the mechanism he uses aims at upholding your original ideas (see previous text). That is why you will never be able to make this work.

And so, when you truly look at the mechanism, you can clearly see that it does not make sense, however, this is so for every aspect of the personality mechanism. So your goal is not to find a 'logic that makes sense', it should be about discovering the true logic. Become aware of the mechanism itself and search for the original judgment that you try to protect as a truth in itself, then let go of your investment in doing so.

By the way, this mechanism also works very well in situations where you adopted conflicting standards, like eating chocolate > nice/pleasant > good and eating chocolate > unhealthy > not good. You can never make this work in the first place ;-)

The fact that you have taught yourself to express these mechanisms more or less socially acceptable, or hide it from your own perception, does not influence the original mechanism at all, and the fact that you can simply become aware of it. It would be very unpleasant having to face all this without having an alternative, which is of course present: you can simply let go of your investment in it, and your inner Self will then effortlessly fill the mental space you thus made available. Which is much more pleasant, logical, natural an peaceful than your personality can ever offer you!