This is so important - it's so hard to gauge what another person's mental model of a scenario is compared to yours.
As in - perhaps OP and 40+ year person had the same, accurate mental model of the probability distribution of success, but OP and 40+ had different attitudes towards risk/reward.
Or perhaps the OP happened to have a much more realistic picture of the probability of success, and 40+ was unnecessarily pessimistic.
So hard to evaluate these things, and to internalise the fact that other people don't have the information you have all the time.
Yep! If I wasn't successful, he would have been right and I can't really blame him too much for thinking it his way. The problem was particularly tricky because it combined bunches of distinctly esoteric domains (OCR, text/vector maps, image processing, fuzzy string matching).. recursively. There were no boundary lines and inconsistently sized black redaction boxes. If I hadn't worked on problems in each domain in separate projects, I doubt I would've been able to do it and he had no way of knowing my experience.
As in - perhaps OP and 40+ year person had the same, accurate mental model of the probability distribution of success, but OP and 40+ had different attitudes towards risk/reward.
Or perhaps the OP happened to have a much more realistic picture of the probability of success, and 40+ was unnecessarily pessimistic.
So hard to evaluate these things, and to internalise the fact that other people don't have the information you have all the time.