It's hard to say what is the meaning of messiness here1. Depending on the situation, you can have different readings of the phrase. Maybe it's creativity, vagueness of actions or, even more generally, everything that differentiates humans from contemporary algorithms2. Whether it's fundamental to humans or not, I feel a good description of messiness will cover the varieties of subjective experiences caused because of uncertainty.
Recently, while travelling via cabs, I have noticed a lot of times GPS navigation applications giving uncannily correct time estimates. Even after finding a pleasant escape from a red patch, the time estimate stays close to the original, and mostly correct. As a driver of such a divinatory vehicle, what choices do you have? Can you really do something that improves your situation? Even though cases like these are, in general, considered to be useful, you can almost always see something frustrating and unfulfilling there.
Probably these kinds of helplessness form one of the key arguments against general algorithmic perversion of human lives. Of course there is this idea that it's fundamentally impossible (intractable in an efficiency sense) to algorithmically define a few processes, but the above example talks about an argument which holds even when we are living in an efficient simulation. The uncertainty need not be true. An illusion will do.
A more satisfactory process of assimilation of algorithms will probably involve accepting subjectivity, whatever that means, as a first class citizen of the human experience and then noticing that a few pieces of present technology landscape explicitly devalue them. Maybe there is a better, even algorithmic, way to understand subjective experiences. Not just something that tries to solve all the problems in a whatever works without costing a fortune sense. Though I am not sure if this argument works since subjectivity itself might be a side effect of such a problem solving approach3.