Have you ever lied to your spouse, thinking you could make up for it with extra kindness later? Have you ever cheated on your taxes, planning to donate the saved money to charity? Have you ever broken your word to a friend, convincing yourself you’d make it right with a bigger favor down the road?
We’re masters at this kind of moral accounting—borrowing against our future goodness to pay for present compromises. And nowhere does this calculus feel more reasonable than in our relationship with God.
Every September, we feel the intensity of the High Holy Days approaching. Rosh Hashanah (the Jewish New Year) comes first, followed ten days later by Yom Kippur (the Day of Atonement). This ten-day period is known as the season of teshuvah (repentance or return). Though sincere repentance is always accepted by God, during this time He is ready and waiting for us to repent, as Isaiah declares:
The Sages teach that this verse refers specifically to the Ten Days of Repentance, when God’s presence is most accessible. Yet many people postpone any serious spiritual reckoning, telling themselves they’ll get serious about God tomorrow, after one more indulgence, one more compromise. They’ve crafted what seems like a foolproof spiritual strategy: live it up now, repent later.
But Jewish tradition tells us that this approach contains a fatal flaw that destroys the very possibility of authentic return.
The Talmud preserves a shocking story that exposes the deadly trap hidden within this seemingly reasonable plan. Rabbi Elazar Ben Dordaya was a man who visited every prostitute in the world—literally every single one. When he heard about a woman overseas who charged an entire bag of gold coins for her services, he crossed seven rivers to reach her. In their final moments together, she made an observation that shattered his world: “Just as this air will never return to where it came from, so will Elazar Ben Dordaya’s repentance never be accepted.”
Her words hit him like a thunderbolt.
Rabbi Yehuda Amital, one of the great Torah scholars of our generation, offered a revolutionary interpretation of this tale that cuts straight to the heart of modern spiritual self-deception. Elazar Ben Dordaya, explained Rabbi Amital, was not simply a man enslaved by lust. He was someone with genuine spiritual aspirations who made a calculated choice to postpone his religious life. He wanted to be righteous, perhaps even a Torah scholar, but first, he planned to systematically exhaust his appetite for worldly pleasure. His manic pursuit of every prostitute wasn’t random debauchery—it was methodical preparation for future holiness.
This perceptive woman possessed street-smart wisdom that many religious people lack. She recognized immediately that her latest client was different. No ordinary person crosses seven rivers for a single encounter. She intuited that this man wasn’t seeking temporary pleasure but executing a grand strategy of systematic indulgence before spiritual transformation. And she knew exactly why such strategies fail.
She understood what Elazar Ben Dordaya had not yet grasped: the path of planned sin followed by planned repentance leads to spiritual quicksand. Every compromise deepens the trap. Every postponement of authentic spiritual life strengthens the chains. What begins as a temporary detour becomes a permanent imprisonment. When she declared that Elazar Ben Dordaya’s repentance would never be accepted, she was warning that he would never actually manage to repent. Though he meant well, he would get stuck in the phase of physical indulgence.
The Sages capture this reality with chilling precision: “Anyone who says ‘I will sin and repent, I will sin and repent’ is not given the opportunity to perform repentance” (Talmud, Yoma 8:9). Based on Rabbi Amital’s explanation, we can understand that this doesn’t mean God refuses to accept sincere teshuvah. Rather, the person who adopts this attitude typically becomes so spiritually entangled that he loses the ability to extricate himself from sin and actually repent.
When Elazar finally understood his predicament, he made another classic mistake. Overwhelmed by the enormity of his situation, he turned to the mountains, valleys, sun, moon, and stars, begging them to intercede for him. Each refused, claiming they needed divine mercy for themselves. Rabbi Amital explains that this reflects how people begin to see themselves as spiritually helpless when they recognize the depth of their condition. In his desperation, Elazar was seeking salvation everywhere except the one place where it actually resided.
The turning point came when Elazar Ben Dordaya finally declared the words that changed everything: “The matter depends only on me!” In that moment, he stopped seeking external salvation and recognized the truth that religious people often forget—each person possesses the inner strength necessary for authentic return. He assumed full responsibility for his choices, mobilized his spiritual resources, and repented with such intensity that his soul departed in that moment of pure teshuvah.
A heavenly voice immediately proclaimed him “Rabbi Elazar Ben Dordaya, destined for life in the World to Come.” The title “Rabbi” attached to his name forever testifies to the transformative power of taking complete responsibility for one’s spiritual condition.
This story demolishes the comfortable myth that we can compartmentalize our lives—indulge now, get serious about God later. But Rabbi Amital’s interpretation reveals an even more dangerous trap: the tendency to see ourselves as spiritually helpless when we finally recognize our condition. In reality, however, the external forces we blame—our circumstances, our past, other people, even our own nature—cannot ultimately prevent our return to God. If we assume full responsibility for ourselves, the path to God remains open.
During these Ten Days of Repentance, when the prophet promises that God is especially “near,” we face a choice that will determine our spiritual trajectory. We can continue postponing authentic change while telling ourselves we’ll get serious tomorrow, next month, or next year. Or we can recognize that the power of transformation lies within us right now.
The God who accepted the repentance of someone who had seemingly exhausted every possibility of sin stands ready to accept ours. But only if we stop seeking complicated external solutions and declare with conviction what Elazar Ben Dordaya finally understood: “The matter depends only on me.”
The choice is yours. And the time is now.
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