Everyone can relate to having things done and said which they would like to undo. Similarly we all experience the reverse, moments and thoughts left undone or unsaid which have come and passed already.

For me personally, being ultra-critical of my own behavior has lead me to much too often err on the side of caution, letting an opportunity pass me by because the reward isn't worth the wager of the risk. More often than not my judgement will tell me at the time, this is only what you want because of impulse and you'll think better of it in a moment, this is what you want to imagine doing but not actually do, this is what you should do according to some personal or societal standard, and these are the things you wont do because they're nonsensical or counter-intuitive.

As a general rule, when I believe I'll regret not doing something in the moment hindsight ends up reinforcing that thought. Despite this, every once in awhile (generally on or near a full moon, by the way) I will rethink my impulse to do [or not do] something despite preferring the idea of not doing it as long as my judgement doesn't have any major red flags. This generally works out for the better more often than not, in the case of doing because usually my inhibitions are simple and pertaining to unfounded paranoia, in the case of not-doing because I have a whole lot of bad ideas which have no business being pursued. This tells me I need to work on being less concerned, paranoid, and scared; and keep myself more grounded in reality. It isn't logical to begin with, but at the time delusional paranoia has a way of making its arguments sound very convincing.

Now that's fine and I have an area to work on but here is the topic of my question: Sometimes the aforementioned type of scenario arise, but all of my judgement screams against it. My better judgement, logical, illogical, even straight up delusional all says run. Despite all of this, I sometimes find myself walking in the direction of the to-be-avoided topic. (Or in the case of the reverse, walking away from something which seems like an amazing opportunity I'd have to be a fool to pass up.) Ignoring every conscious thought, I'll pursue obscure objectives which my mind tells me is risky or dangerous or simply pointless.

Many of these situations simply end with nothing happening at all, no good no bad. Perhaps I unwittingly avoided a bad situation that'll I'll now never be aware of, who knows. But on a few occasions I have found myself in extremely random and unlikely scenario which could not have unfolded in any other way and end up dramatically changing my life, or I end up avoiding an otherwise unforeseeable undesired event. It's these events which has lead me to on occasion ignore my judgement and behave in a way which is completely nonsensical to everyone and myself.

I know there is likely no absolute answer to this question, more-so looking perhaps for methods people use to decide in similar situations, insight into the mechanisms behind this phenomenon and/or how to refine it, insight into why my judgement would be trying to work against me and prevent me from doing something which ends up being beneficial, etc. The latter most in particular is my point of interest, because it seems like self sabotage however my judgement's entire purpose is to preserve my wellbeing and protect me, which generally it does decently.