In medicinal chemistry, my experience has been (half tongue in cheek, but not completely):

There are a large set of "don't do this". When they predict failure, you usually shouldn't go there as these rules are moderately reliable.

There is an equally large set of "when you encounter this situation, try this" rules. Their positive predictive power is very very low.

As a result, a "good" medicinal chemist is one who faced with a million possible things to try, knows the "don't do this" rules very well, and immediately discards 750,000 possibilities. S/he then goes to work on sampling the remaining 250,000, knowing that only 250 or so of them are viable. This person will be 4x as productive as the naive newbee, but will still need a tremendous amount of luck to get more than 2-3 compounds into the clinic in the course of a career. If it happens, its probably due to above average luck more than above average skill.

Or maybe I'm just feeling a little nihlistic today......

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