We have mentioned that regret about past mis-deeds should be relegated to specific times when a person is doing teshuvah.
However, even during this time, when one feels remorse, the regret should not be debilitating. One should feel good about feeling bad.
Harav Yosef Zevin, in Sippurei Chassidim, relates the following story.
In a small village lived a simple man who worked as a wagon driver. We meet him on a cold Friday night as he bursts into the village’s shul.
“Where’s the rav! I must speak to him immediately!” He spotted the rav and rushed over.
“Rav, please help me!” he said, as a look of desperation washed over his face. “I was mechaleil Shabbos (desecrated the Sabbath)! I need a kapparah (atonement). What should I do?”
The rav stared at him. “How? What happened?”
The man looked down at his hands shamefacedly, and spoke in a low voice. “I was returning Erev Shabbos from the market in the next city and I got lost in the forest. I was so panicked that I didn’t even realize that the sun had already set ... until it was too late. “His voice trailed off. “Rav,” he continued, “please help me.”
The rav smiled at him warmly. “Don’t worry. The gates of repentance are never closed. Just donate a pound of candles to the shul to be used for the Friday night prayers and Hashem will forgive you.”
Sitting in the shul and observing this scene was a young man, R’ Yechiel Michel, who eventually became known as the Maggid of Zlotchov. “A pound of candles for violating the Shabbos?!” he thought to himself. “How could the rav treat chillul Shabbos so lightly?”
The next Erev Shabbos, the wagon driver dutifully donated a box of candles to the shul, to be used for the Friday night prayers, but it did not work out. A dog ran into the shul, grabbed them, and ran off. The shocked man ran to report what had happened to the rav.
“Hashem does not want my teshuvah! It’s a sure sign. What should I do now?!”
“Calm down. These things happen,” the rav reassured him. “Just bring another pound of candles next Shabbos. It’ll be okay.”
R’ Michel Yechiel was again in the shul and observed this scene as well. He was now even more surprised at what he viewed as the rav’s cavalier attitude toward shmiras Shabbos.
In any case, this, too, did not work out. The candles were lit the following Erev Shabbos, but within twenty minutes they had all melted down and the shul was left in the dark. And - as you may have predicted - a similar thing happened the third week as well: A strong wind blew out the candles just as Shabbos began and once again the shul was dark.
At this point even the rav grew concerned and told the man to go to the Baal Shem Tov in the neighboring village of Mezhibuzh. So the sincere wagon driver hitched his wagon and traveled to the Rebbe for counsel.
The Rebbe received him and after hearing his story told him, “Never mind. Your rav was right. Just donate another pound of candles and it’ll all work out this time. But when you return to your village, tell the young man who is always sitting and learning in the shul that I would like to meet him.”
The wagon driver did just that and R’ Yechiel Michel immediately set off to meet the Rebbe, but he instead met with all sorts of trouble. His wagon fell into a ditch and the axle broke, so he returned home to have it repaired. He finally set off again but this time he lost his way altogether and by the time he found the road to Mezhibuzh it was late Friday afternoon and the sun was about to set. So he abandoned the wagon and went the rest of the way by foot. Shabbos was well underway by the time Reb Michel reached the Baal Shem Tov’s door. He stood there shivering, not so much from the biting wind and snow, but rather from the trauma of his near violation of Shabbos.
He knocked and after a short wait the door opened. Standing before him was the great Baal Shem Tov.
“Good Shabbos, Reb Michel! Come in. You seem to have had a rough trip. Come sit by the fire and warm up.”
Reb Michel did just that and sat quietly.
“Reb Michel,” continued the Baal Shem Tov. “You are surprised that a box of candles can atone for a sin as severe as desecrating the Shabbos, but that is because you have never experienced the bitter taste of sin - and therefore could not fathom the remorse a Yid feels when he thinks he did an aveirah. Having gone through what you just have, I think you now know the agony the wagon driver feels. Trust me. His remorse alone was more than enough to atone for his aveirah ....”
Of course, the regret, shame, and remorse you feel during the time you set aside for teshuvah will be painful. But embrace that pain. It is the very energy that powers your teshuvah to guarantee that you will receive a full atonement.