Is my teshuvah (repentance) meaningless if I find myself committing the same transgression again? For example, I resolved to be careful not speak badly of others, but after a short while I was back to my old bad habits? Does this mean that my teshuvah was insincere? How often do I have to do teshuvah...?


Our sages tell us that a person's teshuvah is confirmed when that individual is faced with the very same temptation, but refrains from acting on it.

But what if the individual proceeds to repeat the error? Does that mean that the teshuvah was disingenuous? Not necessarily. It is possible to have very genuine feelings of teshuvah but still to mess up again. We're all humans, subject to highs and lows. But if this happens again and again, it is probably time to rethink the whole teshuvah process.

Teshuvah, on its most basic level, consists of two ingredients: a) Remorse for the bad that was done. b) Resolving never to do the offensive act again.

The first component of teshuvah is relatively easy. It's natural to feel regret over misdeeds and missed opportunities. The second ingredient, however, is more difficult. A pledge to improve often grows weaker by the day. The resolution doesn't always have the wherewithal to resist strong impulses and ingrained habits. Something more than a simple resolution is needed.

If a string snaps, a regular knot will not be enough to keep the two pieces together again. A double knot is required. The same holds true with teshuvah. Every sin snaps the "string" that connects a Jew with his Creator. A single-knot, i.e. a simple pledge to never commit the sin again, may not endure. A double knot must be used. In the words of the Midrash: "A man commits a sin . . . what shall he do and live? If he was accustomed to studying one page [of Torah], let him study two; if he was accustomed to studying one chapter, let his study two chapters..."

Don't merely pledge to stop insulting others. Begin praising them! Try to find qualities in the very same people you feel like mocking. Go on the offense and create a teshuvah that will endure...

Incidentally, the area on a string that is double knotted is thicker, stronger, and more difficult to cut than an area that has never snapped before!

For more on this topic, see Broken New Year's Resolutions.

Yours truly,

Rabbi Yisroel Cotlar