After nearly 50 mitzvot are described and demonstrated in Parshat Mishpatim, mostly related to damages and other person-to-person circumstances, the laws enter the realm of the holidays as we are told to “Celebrate three pilgrimage festivals to Me each year” (23:14).
This refers to the mitzvah of “aliyah l’regel,” going up to Jerusalem for the holiday, an obligation on males during the Temple period. (While this mitzvah was incumbent on most males [see Sefer HaChinukh, Mitzvah 88, for exceptions] one wonders what holidays looked like in towns in Israel outside of Jerusalem, if all the men had gone to Jerusalem, with no ability to return home on the holiday… but I digress.)
The Talmud in Rosh Hashana (16b) makes an additional claim in the name of Rabbi Yitzchak, “that every person needs to greet his rebbe on the holiday.”
Leaving aside the likely impossibility of being both “oleh l’regel” and visiting one’s rebbe (and since the idea of visiting the rebbe is sourced to the book of Kings, perhaps it was more widely practiced during non-Temple times), the question that was asked by the Ruzhiner Rebbe (Rabbi Israel Friedman) was, “What is the purpose of visiting the rebbe on the holiday?”
His answer was that just as there can be a righteous person “in his generation,” who might not be considered so righteous were the person to be found in a different era, there can be a person who is viewed as righteous in comparison to others in his vicinity. Some people are righteous in comparison to their neighbors, but were they to come in contact with other righteous people, they may come to see that their righteousness is really nothing to write home about.
Similarly, the Ruzhiner noted, there are people who are considered wealthy (and perhaps generous) in their own towns, but were they to see what the wealthy and generous of other towns achieved and accomplished, they’d see their own efforts were not very impressive. Their wealth is relative, in comparison to their unwealthy neighbors.
How does one prove to these individuals that their righteousness or wealth or generosity is not as impressive as it should be? To the scholar there is an easy answer: “Exile yourself to a place of Torah” (Avot 4). Once the scholar finds himself amongst other scholars, he quickly sees how much he doesn’t know, and how much more has been accomplished by his contemporaries and peers, and he is humbled as a result.
For the righteous and wealthy, the Ruzhiner said, the visit to the rebbe is the litmus test. When all the diverse individuals come to visit their common teacher, each has the opportunity to meet true tzaddikim and truly wealthy individuals.
Being faced with this reality of seeing others who have surpassed one’s own efforts and accomplishments is what he viewed as the antidote to haughtiness.
Confidence is surely a good thing. But how many of us think we are the best at something? How many of us are so proud of our own accomplishments that we look down upon others who have not achieved what we have achieved? How many of us willingly face the reality that there are other people who are smarter, more successful, more wealthy, more generous, more righteous, more scholarly, more learned, more G-d-fearing?
While the logistics of either being “oleh l’regel” without one’s family or going to visit one’s rebbe without one’s family are too complicated for me to wrap my head around, I hope that on a conceptual level we can see how making such a pilgrimage, in either direction, was meant to help a person become grounded in the reality that the world is much bigger than however we see ourselves.
Sometimes we need to open our eyes and see beyond ourselves in order to draw ourselves back to the most basic and fundamental notions: We should always be improving, we have never “arrived,” and the most important Jewish character trait we can display is our humility.