It's supposed to hurt at the beginning, middle, and end - of the finger as well as the time. Barring also needs to be placed properly or else your knuckle will be over the 2nd or 3rd string and will not fret down.
For a lifetime of playing, the only things that seem to escape me are playing fast and barring. Fast I can do without. Barre chords - well - someday.
Best of fortune.
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