Wherever it was he stepped to had its own vast, incomprehensible history, its perils and ecstasies, its potential for unannounced romance and early funerals, but when he was there, it was apparently not as easy for anyone in "Chicago" to be that certain of his whereabouts.
* * * * * * * * * *
Lew is describing another timeline. Probably, by the suggestions of things that could be happening there, a different one each time. Perhaps he even steps into other novels, exiting this one for a slight amount of time while still being able to observe what was happening. So he keeps a connection to Against the Day (or, at least, the Chicago of Against the Day). One can see how he arrived in Against the Day by this method as well. He stepped to the side of wherever he was, entered Against the Day, and then lost the connection with his original world. Perhaps in that moment, he lost both his original past and the past he should have known that was built for him here in this novel. Or, as I've speculated, he simply came over from another Chicago, lost the tether in the same way, and became stuck here.
"it was apparently not as easy for anyone in "Chicago" to be that certain of his whereabouts"
It's as if he still exists as a known character in the book but, for a few moments or so, he is outside the boundaries of the novel, and thus unfindable by other characters in the book. But still observing. Hmm, I guess I said all this in the previous paragraph! I'm pretty sure I've explained myself fully already!
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