Ok, to use your analogy, we are crew members on boats going down a dangerous river. It's full of rapids and waterfalls, and we are each hoping that through skill and luck we'll arrive at the end safely.
But God is watching over it all and he already knows which boats will hit a rock and sink or get washed over the falls and which will get to the end unscathed. That means that no combination of skill and luck will save the doomed boats no matter how hard the crew works at it. They're as good as dead right from the outset.
That's the paradox.
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