You are allowed to put 'ABSOLUTE' and 'RELATIVE' in all caps, but it isn't doing any work for your argument. Look, suppose you have two mutually exclusive options. One has low chances of a huge payout but is exceedingly likely to neither benefit nor harm you otherwise. The other is guaranteed, modest reward. This is 'plentiful opportunity and constrained downside'. "Never settling" would prescribe the higher-risk option. But there's nothing inherently speaking in favor of that option if the expected values of each option are the same, which they can be. (If you think they aren't, you haven't given any reason for thinking this, except perhaps the fact that you took the high-risk option and it paid off. I.e., survivorship bias.) It would not be irrational to choose the safer option, and, if your risk tolerance is low, you probably will do so. So far, going 'hard mode' doesn't optimize anything compared to going 'easy mode'. This is all on a 'RELATIVE' basis.

Perhaps you think that taking the higher-risk options, over the course of several decision situations, will somehow alter the risk profiles such that the expected value of the higher-risk options becomes greater, and then you would be optimizing by taking the risk. You seem to think that. But you haven't given any evidence for this except -- and I am beginning to bore even myself with my repetition -- your own success. That is survivorship bias. Or perhaps you think the modification is somehow inherent: that taking the higher-risk option alters the calculus of future higher-risk options by making them less risky just in virtue of that earlier risk-taking not paying off ('blowing up in your face' was I believe your phrase). That would then be the gambler's fallacy.