The Higher Path of Teshuvah
The Midrash presents a perplexing discussion on the topic of teshuvah:
אמרו לו תלמידיו לרבי אליעזר, רבינו “אמור לנו היאך נעשה תשובה ונחיה.” מיד פתח ואמר, “יענך ה’ ביום צרה”, זו היא שנאמר ברוח הקודש על ידי שלמה בן דוד מלך ישראל, “דודי שלח ידו מן החור ומעי המו עליו.”
Rebbe Eliezer the Great was once asked by his disciples: “Rabbeinu, teach us how to do teshuvah, so that we may live.”
He answered them by citing the verse “May Hashem answer you on the day of trouble.” This is as Shlomo, son of David Melech Yisrael, said in his Divine inspiration, “My beloved reached his hand through the opening, and my innards longed for him.” 
What exactly did his disciples mean to ask? Were they unaware of the laws of how to do teshuvah and atone for their sins? If so, how did the verse, “May Hashem answer you on the day of trouble,” answer their question? And what relevance to this has the following verse, “My beloved reached his hand”?
Although the disciples perhaps did understand the principles of teshuvah, they specifically wanted to know how to do teshuvah and live. The path of teshuvah that leads to bitter remorse and somber contrition was well known to them, but they asked for guidance on a different, higher path of teshuvah, which leads to holy vitality and joy.
The Gemara tells the story of Rebbe Elazar ben Dordia:
אמרו עליו על רבי אלעזר בן דורדיא, שלא הניח זונה אחת בעולם שלא בא עליה. פעם אחת שמע שיש זונה אחת בכרכי הים והיתה נוטלת כיס דינרין בשכרה, נטל כיס דינרין והלך ועבר עליה שבעה נהרות. בשעת הרגל דבר הפיחה, אמרה: “כשם שהפיחה זו אינה חוזרת למקומה, כך אלעזר בן דורדיא אין מקבלין אותו בתשובה.”
הלך וישב בין שני הרים וגבעות, אמר: “הרים וגבעות בקשו עלי רחמים,” אמרו לו: “עד שאנו מבקשים עליך נבקש על עצמנו,” שנאמר: כי ההרים ימושו והגבעות תמוטינה. אמר: “שמים וארץ בקשו עלי רחמים.” אמרו: “עד שאנו מבקשים עליך נבקש על עצמנו,” שנאמר: כי שמים כעשן נמלחו והארץ כבגד תבלה. אמר: “חמה ולבנה בקשו עלי רחמים,” אמרו לו: “עד שאנו מבקשים עליך נבקש על עצמנו,” שנאמר: וחפרה הלבנה ובושה החמה. אמר: “כוכבים ומזלות בקשו עלי רחמים,” אמרו לו: “עד שאנו מבקשים עליך נבקש על עצמנו,” שנאמר: ונמקו כל צבא השמים. אמר: “אין הדבר תלוי אלא בי.” הניח ראשו בין ברכיו וגעה בבכיה עד שיצתה נשמתו. יצתה בת קול ואמרה: “רבי אלעזר בן דורדיא מזומן לחיי העולם הבא”.
בכה רבי ואמר: “יש קונה עולמו בכמה שנים, ויש קונה עולמו בשעה אחת.” ואמר רבי: “לא דיין לבעלי תשובה שמקבלין אותן, אלא שקורין אותן רבי.”
It was said of Rebbe Elazar ben Dordia that there was not one woman of ill-repute in the world whom he had not visited. Once, he heard that there was a woman in a distant country who charged a purse full of gold coins as her fee. He took a purse of coins and travelled to visit her, passing over seven rivers in his travels. As he approached her, she passed wind.
“Just as this wind can never return to its place, so Elazar ben Dordia will never be accepted in teshuvah,” she said.
He then went to sit among the mountains and the hills. “Mountains and hills, beseech Hashem for mercy on my behalf,” he said.
“Before we pray for you, we will pray for ourselves, as the says, ‘The mountains will be displaced, and the hills will fall,’” he imagined them to answer.
“Heavens and earth, beseech Hashem for mercy on my behalf,” he said.
“Before we pray for you, we will pray for ourselves, as the possuk says, ‘The Heavens will be dispersed like smoke, and the earth will be worn out like a garment,’” he imagined them to answer.
“Sun and moon, beseech Hashem for mercy on my behalf,” he said.
“Before we pray for you, we will pray for ourselves, as the possuk says, ‘The moon will be disgraced, and the sun will be shamed.’”
“Stars and constellations, beseech Hashem for mercy on my behalf,” he said.
“Before we pray for you, we will pray for ourselves, as the possuk says, ‘The hosts of Heaven will melt with fear.’”
“It all then depends on me,” he concluded. He hung his head down and wept until he passed away. A Heavenly voice then announced, “Rebbe Elazar ben Dordia is invited to the World to Come…”
Rebbe (Yehudah HaNassi) cried and said, “Some earn their portion in the World to Come over the course of many years, while others earn theirs in just one moment. Not only are baalei teshuvah accepted, but they even earn the title of Rebbe.”
We thus have a precedence in which the baal teshuvah’s penitence is fully accepted, he is invited to the World to Come and he even earns the title of Rebbe. Nonetheless, this involved tears of contrition that were so powerful that Rebbe Elazar ben Dordia actually died of remorse. Is this the only path, or is their perhaps another aspect of teshuvah through joy?
Rebbe Eliezer therefore explained that teshuvah begins with the painful recognition of one’s faults, as we say in the special prayers for the fast days, ” כי בצרה גדולה אנחנו – for we are in great trouble.” Nonetheless, the baal teshuvah ultimately finds joy and courage with the realization that Hashem will certainly answer him in his suffering and accept his teshuvah with love, as David HaMelech said, ” יענך ה’ ביום צרה – Hashem will answer you on the day of trouble.” To the degree that we humble ourselves in sincere teshuvah, Hashem uplifts us and plants joy and fulfillment in our hearts.
The Rambam writes:
גדולה תשובה שמקרבת את האדם לשכינה… אמש היה זה שנוי לפני המקום משוקץ ומרוחק ותועבה והיום הוא אהוב ונחמד קרוב וידיד.
Great is teshuvah, in that it endears a person to the Shechinah. Yesterday he was hated by Hashem, detested, rejected and loathsome; but today he has become beloved, favored, endeared and befriended.
Since Teshuvah attaches a person to the Creator with bonds of love, there can be no greater joy in the world, as David HaMelech said, ” ואני קרבת אלקים לי טוב – As for me, closeness to G‑d is my good.”
The Midrash therefore concludes with a verse from Shir HaShirim, “My beloved reached his hand through the opening, and my innards longed for him.” The signs of favor and reconciliation that a baal teshuvah merits to receive from his Creator cause his heart to overflow with joy, fulfillment and a sense of longing for Hashem which Hashem reciprocates with love.
Thus, Rebbe Eliezer explained that although teshuvah does begin with awe, trembling and contrition, it eventually leads us onto the path of joy, upon which we can return in teshuvah and live with happiness and peace of mind forever after.
(The death of R’ Elazar ben Dordia is not proof to the contrary, since R’ Elazar was also guilty of the sin of heresy, as the Gemara there explains, the teshuvah for which works on an entirely different system.)