I'm not strictly endorsing the original proposal. But if we think some degree and certain types of pain adds depth to our personalities and enriches our existence then the question becomes how much pain and what kinds of pain should we let ourselves experience. We probably want to say no to water-boarding and yes to mild disappointment and scraped knees. A world without heartbreak (which I realize isn't the same thing as forcing people to experience heartbreak) seems to involve costs: fewer tragedies get written, people don't understand love quite the same way, no one understands pop music from the 20th century, etc. I'm not sure how one even begins to weigh the costs and benefits.
Making everyone experience heartbreak seems like going too far to me but in exactly the same way scraped knees are going too far according to the Super Happies.
I'm not sure how one even begins to weigh the costs and benefits.
It's not a trivial problem. But I think if I don't at least attempt such a weighing, I'm not taking the problem seriously.
For my part, it makes no sense to me that the actual suffering should ever be valuable enough to want either to participate in it or to encourage others to do so. If having suffered through X is valuable, then I might encourage taking on the memory of having suffered through it, but that's no reason to make them go through X. (Assuming, of course, that my communication...
Utopia and Dystopia have something in common: they both confirm the moral sensibilities you started with. Whether the world is a libertarian utopia of the non-initiation of violence and everyone free to start their own business, or a hellish dystopia of government regulation and intrusion—you might like to find yourself in the first, and hate to find yourself in the second; but either way you nod and say, "Guess I was right all along."
So as an exercise in creativity, try writing them down side by side: Utopia, Dystopia, and Weirdtopia. The zig, the zag and the zog.
I'll start off with a worked example for public understanding of science:
Disclaimer 1: Not every sensibility we have is necessarily wrong. Originality is a goal of literature, not science; sometimes it's better to be right than to be new. But there are also such things as cached thoughts. At least in my own case, it turned out that trying to invent a world that went outside my pre-existing sensibilities, did me a world of good.
Disclaimer 2: This method is not universal: Not all interesting ideas fit this mold, and not all ideas that fit this mold are good ones. Still, it seems like an interesting technique.
If you're trying to write science fiction (where originality is a legitimate goal), then you can write down anything nonobvious for Weirdtopia, and you're done.
If you're trying to do Fun Theory, you have to come up with a Weirdtopia that's at least arguably-better than Utopia. This is harder but also directs you to more interesting regions of the answer space.
If you can make all your answers coherent with each other, you'll have quite a story setting on your hands. (Hope you know how to handle characterization, dialogue, description, conflict, and all that other stuff.)
Here's some partially completed challenges, where I wrote down a Utopia and a Dystopia (according to the moral sensibilities I started with before I did this exercise), but inventing a (better) Weirdtopia is left to the reader.
Economic...
Sexual...
Governmental...
Technological...
Cognitive...