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"squaring" off your toenails ensures that the edges are outside of the skin on your toes, preventing ingrown toenails and the nasty festering results. Squared off isn't as important as much as just making sure you don't cut too far into the edges.
Just ensure that your left and right edges of your toenails are not occluded by your toe when looking directly down. If you see skin before the edges you're going to be wrong, eventually they'll grow into your skin, and I'll be there with a pair of pliers, silver nitrate and a big smile.
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