I recently wondered whether it's possible that transhumans would spend parts of their lives in situations very similar to Dante's hell, complete with wailing and gnashing of teeth. Some have suggested that a bit of pain might be necessary to make all the pleasure we're supposed to get realizable, but I suggest that we might actually need quite a lot of it. If the only way to make people happy is to improve their lives, pushing them way down might turn out to be a reasonable solution. And some might choose that route to spice up whatever other sources of happiness there are. The fact that hellfire scares us fleshlings wouldn't matter to indestructible nanocyborgs.
Or maybe they would intentionally seek other things that I consider horrible. Like the risk of death - isn't that what people do already when they walk on a tightrope?
Why not just implant memories of hell?
Perhaps they'll put everyone in hell for a few minutes and mess with their memory so they think it was always like that, then disable long-term memory writing and take them out. It would be like you just left Hell for your entire life.
No matter what method they use to get you to the pinnacle of happiness, I'd think disabling long-term memory storage at that point and keeping you there forever would be the best. At least, unless that wouldn't be happiness.
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...