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One of the reasons paperwork/any dealings with any sort of impersonal API are so dreadful is that there is no way to add meaning. The game is finite (form filling has less material depth to it, especially when digital) and any counterparty is figuratively or literally robotic.
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We probably overuse the infinite game/finite game model around here, but "adding meaning" is nearly synonymous with "find the infinite game dimension of a seemingly finite activity and develop it." Call this operation "infinitizing". It can be done in material or social ways.
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Material way is basically mindfulness++ any of a category of behavioral augmentations ranging from simple changed perception of behavior to active exploration of an infinitizing dimension (which typically feels like play because it is almost decoupled from finite function aspect)
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Social way is managing to find a counterparty in able and willing to engage in a sort of deepening mutuality. So far this means a willing and able human. AIs haven't yet reached capability of being infinitizing counterparty and may be definitionally incapable of it.
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It's not a "doing" problem I suspect. It's a definitional problem. A square can't become a circle by trying harder. It has to go on a Square's Journey.
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Intelligence is easy. The problem I'm flagging here is counterparty being human in a different way... capable of feeling pain etc. Much harder, and more closely coupled to hard problem of consciousness than to AI. If you are a strong AI type, you won't see this as a problem.
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