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I'm thinking what we've been watching is not the Losties' first time "around" on the island. The fact that we've been shown Jacob going to some of the key characters as children makes me believe he's trying to change future events that have already happened due to the actions of the Losties. He'd had no reason to go to them as children unless he already knew what was coming, which means it already happened. WHH!? I guess my point is this: The first time we see Jack wake up in the jungle in the pilot is NOT his (or anyone else's) first time on the island. Maybe this time "around" on the island is the "progress" that was spoken of. Does this make any sense?