People sometimes think, "Do I really have to work on humility? Is that an obligation? I've heard of Yirat Shamayim, But where is humility on the list of things that I have to work on?"
At the beginning of the Bet Halevi's essay on arrogance and humility, he points out that arrogance is a sin. So of course you have to work on it. But there are a lot of things that are sins. Is this something that has to be at the top of my radar? Is it a priority? We hear about movements of Ahavat Yisrael/love your fellow man, and we have movements about that. There's a movement to guard your eyes, as well. But I haven't yet seen a Ga'avah movement where people say, Make Klal Yisrael Humble Again. We don't find such initiatives out there. So let's quote a pasuk in Mishleh from the wisest of men, Shlomo Hamelech,
טו (כח) לֵב צַדִּיק יֶהְגֶּה לַעֲנוֹת: /The heart of a righteous person will considers what to answer.
Simply speaking, Rashi and other commentaries understand the word לענות means to answer.
Rabbenu Yonah, in his commentary on Mishleh, has a different explanation.. He says the root of the word לענות is the same as ענו /humble or עני /poor Rabbenu Bachye, in his introduction, Parashat Bahar Vayikra 25:1 brings down this pasuk (as in his introduction to many, parshiot, he brings down a pasuk in Mishleh) and he says that the word laanot is the same as the term used when Hashem spoke to Paroah So said God, the God of the Hebrews,
עד מתי מאנת לענות מפני/Until when do you refuse to humble yourself in front of Me. Rashi says on that word, לענות follow the Targum. The Targum says, להתכנעא which means to be to be humble. And the root of the word he says is Ani/poor.
Base on this Rabbenu Yonah explains the pasuk. He says, the Sadik is always thinking of ways to humble himself.
Rabbenu Bachye in that same spot says that's the defining aspect of a sadik. The sadik is someone who humbles himself.
And now for Rabbenu Yona's powerful words, יש צורך למערכי לב להתמדת הצעות במחשבות להגיע אל הענוה ולאהוב את השפלות, A person must create compositions in his heart to constant ideas and thoughts to reach humility into being lowly.
So Rabbenu Yonah doesn't just say it's a fleeting thought. Rather, there is a need to create compositions constantly, with new ideas on how to become humble.
Rav Wolbe used to quote another Rabbenu Yonah in Shaare teshuva (Shaar ג letter 15(, where he's talking about the requirement to have Yirat Shamayim. And he says people that are not constantly creating compositions and thinking and understanding, the prophet says strong words about them,
Rav Wolbe used to say the term, Orchim Maracha is used by Rav Akiva Eiger, one of the great giants of yesteryear, who wrote a 20-30 piece essay on a topic and called a Maracha. It's like a composition. He says, that's what you have to do for Yirat Shamayim. And I'll add that Rabbenu Yona uses the same word of Orchim Machshevot on humility. These are similar words- where in Shaare Teshuva he says, Letitbonen Tamid, here he says, hatmada/ consistent thoughts.
So it may seem like it's a contradiction, to have Anava and Yirah at the same time but we can answer based on another pasuk in Mishleh 22:4. עֵ֣קֶב עֲ֭נָוָה יִרְאַ֣ת יְהֹוָ֑ה עֹ֖שֶׁר וְכָב֣וֹד וְחַיִּֽים׃ / The result of humility is fear of Hashem.
The Artscroll commentary on Mishleh quotes from Siftei Chaim, that says, "Arrogance is the primary obstacle to recognizing Hashem. Such a person finds it hard to acknowledge that his abilities are gifts of Hashem for such an awareness would impinge upon his sense of self-importance.
A humble person, however, knows he is a minute creature controlled by Hashem, so he automatically develops the fear of Hashem.
So we no longer have a contradiction.
Rabbenu Yonah is saying both are true. You need to constantly think of ways to have Yirat Shamayim and you have to constantly think it's about being humble because it's one and the same.
Rav Wolbe, in his sefer Alei Shor (vol 2 Page 141) on the topic of the learning Mussar in the unit Marechet Limud Mussar/Composition on Learning Mussar, mentions sources and discusses how Mussar is not a new creation. Everything we have is tradition. He quotes from different Amoraim from the Gemara that use the technique of mussar, which is repeating to yourself important principles to penetrate your heart. He quotes from Sanhedrin7A, that when Rav, an Amora, would see a crowd of scholars following him, (fearing that he might get arrogant) he would say the following verse from Iyov 20:7 to himself: כְּֽ֭גֶלְלוֹ לָנֶ֣צַח יֹאבֵ֑ד רֹ֝אָ֗יו יֹאמְר֥וּ אַיּֽוֹ׃ If his stature rises to the heavens, he shall perish forever like his waste
Rav quoted this pasuk to avoid getting haughty from all the people are following him . He reminded himself, Calm down. As high as you get, you're not going to be here forever.
In a similar practice by Mar Zutra Hasida/the pious, his students would carry him on their shoulders during the Shabbat of the festival discourse when everyone would gather together He would say the pasuk from Mishleh 27:24 כִּ֤י לֹ֣א לְעוֹלָ֣ם חֹ֑סֶן וְאִם־נֵ֝֗זֶר לְד֣וֹר (דור) [וָדֽוֹר]׃ /For riches are not forever And does the crown endure for all generations?
So these greatest of the greats were giving themselves Mussar, lest they fall prey to the challenge of arrogance.
For a more modern story on the same topic, there is a story is in the Maggid Speaks, the original book by Rabbi Pesach Krohn, which are stories and parables of Rav Shlomo Schwadron z'l the Maggid of Yerushalayim (see page 154).
Rav Isser Zalman Meltzer the great Rosh Yeshiva of Yeshivat Etz Chaim (1870 to 1953) was always careful not to write on Chol Hamoed. (People are careful not to write unless it's an emergency, or some kind of a loss or damage would be incurred if you don't write.) but he asked his nephew for a pen and ink to write something. The nephew wanted to know what the emergency is. Under pressure, Rav Isser Zalman revealed that, " On Chol Hamoed, a lot of people come to visit me. I have the ability to look into people. When I'm talking to them, I'm immediately aware of a person's virtues and faults. It hurts me to know the faults of people who come to visit me. Additionally, knowing another's faults can lead me to become arrogant. So I devised a plan: Shlomo Hamelech in Mishleh 4:25 writes,
עֵ֭ינֶיךָ לְנֹ֣כַח יַבִּ֑יטוּ וְ֝עַפְעַפֶּ֗יךָ יַיְשִׁ֥רוּ נֶגְדֶּֽךָ׃ /Let your eyes seek honesty and your brows search straightforwardly before you.
Now the word lenochach which here is used for honesty, is usually translated towards yourself. So now there's a new meaning. Let your eyes seek yourself. In other words, look at yourself. See your own faults instead of the fault of others. I always keep this pasuk in front of me on a small piece of paper as people are talking to me. It helps me avoid Gaava. But now I can't find that slip of paper. It's an emergency. I have to write this down now, lest I fall into arrogance."
Many years after Rav Isser Zalman passed away, Rav Shlomo Schwadron was sitting in the Succah of Rav Isser Zalman's son-in-law on Chol Hamoed and he told over the story. Rav Isser Zalman's daughter, who was listening to the story as well, left the Succah and came back with a smile on her face and a sugar bowl in her hand. She said, "This is the sugar bowl my father kept on his table and on the sugar bowl was etched this pasuk עֵ֭ינֶיךָ לְנֹ֣כַח יַבִּ֑יטוּ וְ֝עַפְעַפֶּ֗יךָ יַיְשִׁ֥רוּ נֶגְדֶּֽךָ׃
He kept it in front of him, but in a hidden way, to give himself this message. This is how the Greats became great, by constantly looking for ideas to humble themselves.