Ki Tavo and Rosh Hashana: Please Hashem!....Let Us be to the Head and not the Tail

One of the blessings in Ki Tavo is that we will be the head and not the tail if we follow the Torah. The custom of eating the head is not found in the Gemara but brought by the Shulchan Aruch. But Pirkei Avot seems to imply that it's not always good to be the head?

What does it mean to be the head?

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