Tough Choices and Disappointment

I'm not sure I subscribe to this conception of choice, nor disappointment.  To me, disappointment comes from a failure to believe that the world was as it is, and a sense of loss that something you'd hoped/believed is not true.  And that's not really connected to choices, which are generally about how to prioritize a multi-dimensional (perceived value over time, at least) future preference.

I think the "tough" choices are those where the net values of the options are similar (that is, it's non-obvious), but there's a large difference in the timing and/or certainty of the outcomes, so there's a perceived importance of the choice (that is, it's going to seem obvious in retrospect).    To that extent, we're agreed: these are decisions where you risk feeling like you've made the wrong one later.

I do completely agree with the overall advice - accept the world first, then make a decision un-influenced by your surprise or disappointment in that situation.  

Small nitpick about English: it's "life expectancy", not "live expectancy". 

I've certainly had many tough choices that were not preceded by disappointment, so I can't relate to the premise at all.

As a comment on English usage, I'm not sure about the intended meaning of "I think this is so obvious that it's most certainly true in most situations". When taken literally, qualifiers such as "I think" are redundant. You wrote it, so you thought it. In practice they are used to reduce the expressed confidence of a statement. However, then you go on to say "it's obvious", and "most certainly true" which are extreme statements of high confidence. Then you weaken it again with the qualifier "most situations" which contradicts the phrasing in the opening sentence "[...] always preceded by a disappointment."

I am left with contradictory information about how strongly you believe this hypothesis, which rather defeats the whole point of an epistemic status.

I think this is similar to Post #25 of Nate Soares' 'Replacing Guilt' Series : Choose Without Suffering. "Humans tend to get grumpy when confronted with a bad option and a worse one." His advice, which I broadly agree with, is to weigh our options in relation to one another and not against any absolute sense. A useful tool he offers to tackle decisions like this is to use a hypothetical "What If?" The choice is easier to make when we imagine a world in which all our choices will lead to bad outcomes. "When given a choice between bad and worse, you need to be able to choose 'bad' without qualm."