Parshat Ki Tavo: Heads and Tails
Deuteronomy 28:44

ה֣וּא יַלְוְךָ֔ וְאַתָּ֖ה לֹ֣א תַלְוֶ֑נּוּ ה֚וּא יִהְיֶ֣ה לְרֹ֔אשׁ וְאַתָּ֖ה תִּֽהְיֶ֥ה לְזָנָֽב׃

“He [your foe] shall be your creditor, but you shall not be his; he shall be the head and you the tail.

The Torah appears to say that it is always better to lead than to follow. The assumption is that being a follower – “the tail” – is a fate worthy of making this terrible list, while being a leader is a blessing. 

This is not that case. In Pirkei Avot, we learn that sometimes it is better to be the tail than the head! “Be a tail unto lions, and not a head unto foxes.” A example of this is the talmudic sage Resh Lakish, who gives up being the head of a band of thieves to learn Torah with the greatest Rabbis of his time. He was the head of foxes, and opted to be the tail to lions.

The curse can’t be that one will simply be a follower. Rather, the curse is that one will follow someone who is leading them astray. All of us are led one way or another. Be it teachers, headlines, friends, stories, music – there is an array of people and ideas that guide our actions. If we do not examine these forces critically we may act in a way that is guided by falsehood and ego rather than truth. 

I would amend it this way: It is a blessing to be the head, and a blessing to be the tail. It is a blessing to be a leader of ones own conscious and intellect to determine with wisdom what people and ideas to adhere to.