Reacting to the full blog post (but commenting here where the comments have more potential to ferment something based on attention)...

This reminds me of CFAR's murphyjitsu in the sense that both are (1) a useful guide for structuring one's "inner simulator" to imagine spefific things to end up with more goal-seeky followup actions (2) about integrating behavior over long periods of time that (2) can probably be done well in single player mode.

The standard trick from broader management culture would be a "pre-mortem" which is even further separated by... I think basically leaving people to not focus on the mental actions, and often deployed by managers for teams, to try to get them on the same page about possible future failure conditions that the team could potentially mitigate.

The big difference between telescoping and both of these is that telescoping is "more positive". It is asking about goals instead of fears :-)

One interesting thing is to ask whether there's any evidence anything like this actually helps in practice and/or to tease apart the mechanisms whereby it helps, if it does. Wikipedia cites a 1989 managerial/business/psychology study on "prospective hindsight" with this title and abstract...

Back to the future: Temporal perspective in the explanation of events.

Examined how shifts in perspective might influence people's perceptions of events by investigating 2 possible factors: temporal perspective (whether an event is set in the future or past) and uncertainty (whether the event's occurrence is certain or uncertain). In the 1st experiment, which involved 114 MBA students, temporal perspective showed little influence while outcome uncertainty strongly affected the nature of explanations for events. Explanations for sure events tended to be longer, to contain a higher proportion of episodic reasons, and to be expressed in past tense. Evidence from the 2nd experiment, which involved 76 MBA students and 32 nonstudent adults, supports the view that uncertainty mediates not the amount of time spent explaining, but rather Ss' choice of explanation type. Implications for the use of temporal perspective in decision aiding are discussed

Mechanistically, this suggests that "certainty" is a key parameter and so it might be interesting to "suppose that a year from now you were very sure that the year had been surprisingly good... why?" vs maybe something like "imagine that someone is hired to assess your life objectively a year from now (they are uncertain because they're new, and you must have hired them because you yourself are uncertain) and they ask about how it went... what will they be told and/or ask about?"