Two of the questions I addressed regarded the issues of dealing with the inevitable slumps one faces in this yearly, most daunting task of achieving repentance, and methods to making lasting and meaningful kabbolos - resolutions.

My response was based on an article I wrote several years ago, condensed here:

Dread, frustration, disappointment and despondency are just some of the emotions that begin to erupt as we face the reality and implications of Yom Kippur.

We dread facing our personal deficiencies, frustrated with our paltry and insincere regrets, disappointed in ourselves, leading us to hopelessness in our ability to ever repair our relationship between ourselves, our fellow man and Hashem.

On Yom Kippur we make a last-ditch effort at meaningful change, yet, the moment Yom Kippur is over we are right back to our old habits.

There are three components to doing תשובה, repentance: חרטה, regret, עזיבת החטא, abandoning the sin, and קבלה על העתיד, accepting to change in the future.

Can we sincerely state we have regretted our sins when we consistently return to them time and again? Regretting what we know we will inevitably continue to do compound our frustration with ourselves.

Is it really within our 'choice' to change abruptly from all that we have done wrong? Some things are simply beyond our unique level of free will. Even those areas that are in our reach, have become distant from us because of our poor choices, and can’t be undone in an instant.

Haven’t we proven ourselves lacking in the commitment to no longer sin by the very fact that from year to year we seem to be in the same place?

Perhaps our error lies in our perspective. When we view our lives on Yom Kippur as a checklist of failures and seek to undo them entirely, we are doomed. We don’t possess yet enough understanding of sin to give us a true sense of regret. That takes a lifetime of avodas Hashem.

חרטה, can more aptly be translated as sensing a deep sense of loss, a feeling of emptiness that is “etched” into our consciousness. Only when one fathoms the relationship properly can one first fully appreciate the sense of failure.

But we can emote a deep yearning to get closer, and a healthy 'regret' that we are not there yet. This passionate expression of a desire for closeness is more easily 'etched' into our being and provides a much healthier power of 'regret'. The critical difference between the two is that this second one leaves us hopeful. It stems not from failure but rather from aspiration.

Instead of desperately trying to focus on undoing our 'misdeeds' entirely, we can try to undertake a plan to get ever closer. By taking upon ourselves to improve an area that is within our reach and doable, we begin to convey our striving for closeness with tangible evidence of our goal. This will encourage us rather than defeat us.

There is one caveat however with this approach. In the past when we undertook a sweeping repentance it was unrealistic and thus not fully accountable. When we promise to make small pragmatic change however, we will be held fully responsible to maintain it. It is within our reach!

I added, that in order to make an effective commitment it is important to select something that represents our not merely being 'better' but that exhibits before Hashem that we have changed. Rav Hutner explains that the judgment we undergo on Rosh Hashana determines the sum total of who we are and where we are heading. It is for that reason the Rambam says its not enough to simply add credits during the Ten days of Repentance but one must do teshuva, for only a sincere desire to change the course of our life that reflects on our being transformed from the individual who stood before Hashem on Rosh Hashana, is deserving of reconsideration on Yom Kippur.

Furthermore, if the resolution relates to an area, we particularly struggle with, how much more so that choice to restrain, reflects on our altered state. Reb Tzadok taught that those aspects of our life we battle with, are the targets Hashem wants us to aim at.

When I was a young teenager, I was fortunate to have inspiring role models in my life. Growing up in the early sixties, I was exposed to television, movies, and a rapidly changing set of world values, that was stunningly fresh and alluring.

I remember vividly at the age of thirteen, standing in front of a movie theater together with a dear friend, who today is a Rosh Kollel, Rav and author of sefarim, living in Israel, and made a pact to never enter a movie theater again. We never did. Although we subsequently still listened to, and saw, many things we shouldn't have, but that 'small' kabbola, transformed us and sent us on a trajectory to an inspired and healthy path in life.

Ten years later, that same friend would visit during bein hazmanim from Israel to spend time with his family in New York. I'd pick him up each day in my car and drive together to a local Bais Midrash, relishing the opportunity to once again learn with each other.

Smartphones and CD players, and for that matter cassette decks in cars, hadn't been invented yet, and all we had was the radio for mindless entertainment. Inevitably, each time I picked him up the radio would be playing tuned to either 1010 WINS or WCBS, two news stations. Whenever he would enter the car, he would wonder aloud why I had the need for the constant stream of distraction, when I didn't seem to be attentive to it, and allowing it to play even while we conversed. Then and there, I resolved to never be tethered to mind numbing background noise and committed to become more mindful of who I was, permitting myself to think. A small kabbola with great repercussions.

Lastly, another ten years down the pike, I like many would receive daily the newspaper, and read up on all the 'vital' sections of the paper that possessed critical inconsequential information, especially the 'funnies' and their story lines.

Once again, the echoes from my past encouragingly whispered to me, wondering how I could have become 'hooked' on such purposeless nonsense, I quickly resolved to quit cold turkey, restoring my mind to mental sanity once again. One small step for a man, one giant leap for Hashem!

I do not aver to having achieved greatness, but certainly recognize how even small steps can bring you to the most remarkable destinations.

באהבה,

גמר חתימה טובה,

צבי יהודה טייכמאן