The Western culture looks upon death as the ultimate disaster or punishment and fighting against it an admirable and courageous act. Yet it's the most natural and inevitable passage for all living things.
I have no idea if Jerry consciously picked the time to pass. However, almost all NDE stories tell of the most wonderful feeling upon death though they choose reluctantly to return to life for unfinished businesses. Jerry might have realized he had lived a full life and chose to continue on blissfully beyong the point of no return, knowing well Esther had her path to continue and would be OK without him.
eta ALG has expressed very well similar concept while I was writing my post.
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