Yom Kippur is upon us once again. A looooooooong day of fasting, fretting, apologizing… we all know the drill by now. But in all seriousness, Yom Kippur is a tremendously powerful opportunity where you can attain a connection with Hashem unlike any other time. The teshuvah process is an intimate and introspective tool God gives us to not only fix our chets (inaccurately translated as sins) but to turn them into merits.

In brief, the teshuvah process involves four steps. Regretting the act, Stop doing the act, Articulate aloud that the you did the act and that it was wrong (this is known as Viduy), and finally Resolving to never to do it again. And that’s great if you’re finally ready to own up to your mistakes and make a fresh start.

Never Say Never Again?

But what if you know you’re going to do that chet again? A Jew is never supposed to get angry and it is something you should do teshuvah for. But does God honestly believe you’ll never get angry again? What about for other things? Maybe you’re trying to quit smoking, but eventually you’re going to have one of those days and before you know it you’ve gone through a whole pack. Can you do teshuvah when sooner or later you’re going to break? According to Rambam;

“Anyone who verbalizes his confession (Viduy) without resolving in his heart to abandon sin can be compared to one who immerses in a mikveh while holding the carcass of a lizard in his hand.” (Hilchot Teshuvah Ch 2:3)

The idea being that if one uses the ritual bath (mikveh) to purify themselves, holding a dead animal completely negates the process. So too, doing the teshuvah process when you plan to transgress defeats the purpose. It would seem that Rambam is saying we just shouldn’t bother if we can’t let go of our most flawed and deeply embedded character traits. But maybe that’s not the whole story.

Maybe, maybe not.

The reading of Parsha Vayelech starts out,

“Today I am one hundred and twenty years old. I can no longer go or come, and the Lord said to me, “You shall not cross this Jordan.” (Devarim 31:2)

Now why does Moses feel the need to tell the Jewish people he can no longer “go or come” when he immediately says God told me I “shall not cross,” the Jordan? He should just say the second part, God says I can’t go. Rabbi Noach Weinberg used to speak about the idea in the reverse. When we say, “I can’t,” we’re denying God. Because in truth, we put out the effort and God is who actually accomplishes the deed.

But here Moses is focusing on what he can’t do. What can we learn from this? Rabbi Shmuel Gluck brings down a tremendous insight. We struggle with so much of what we know we shouldn’t do and, to be more specific, what the Torah tells us we can’t do. And the reason why we’re so ambivalent is because of what he refers to as the maybe factor. 

He brings in an example of a young couple dating. Let’s say the boy is really into the girl, but unfortunately the girl breaks things off. For years the boy dates but never can find anyone he likes. Then the girl gets engaged and married. Suddenly within a year, the boy gets serious and gets married himself. What happened? Was he just being super jealous? No. According to Rabbi Gluck, the boy is stuck in the maybe factor hoping to get back together with the girl. Now with that no longer an option, he finally is forced to look at reality.

We all fall into this trap with the things we want but shouldn’t. An appealing piece of cake, someone off limits that catches our eye, the handicap spot when we’re going to only be a minute and there’s not parking anywhere! These are only struggles when we entertain the possibility of infringing upon them.

“If we are going to look at the restrictions in the Torah as ‘I’d like to, but I’m not allowed to,’ there’s the maybe factor. If we could train ourselves to think, ‘I can’t do this,’ not ‘I’m not allowed to’, but ‘this I can’t do’… we negate the maybe factor from our minds… we find ourselves more consistently able to remove the resistance that causes us so many problems.”

Declaration on the Day

It’s a big jump to make that decision. It takes emotional intelligence, self awareness, and a tremendous wrestling with long harbored inner turmoil. And even with the negation of the maybe factor we still may transgress someday. So with that, are we still going into the mikveh with the dead lizard?

Rabbi Denbo points out the crucial difference.

“If someone were to ask you, ‘if it was within your power to not make this mistake ever again’, would you choose that?”

If you are able to emphatically say yes, then on Yom Kippur you can absolutely do teshuvah for that act.  It is tremendous to be growing and making progress in abstaining from whatever it is we struggle with. But if deep down you’re holding out until you feel you’ve done enough good to justify indulging, then the teshuvah doesn’t work to its true potential. Is it a form of teshuvah? Sure. But to really make a change, we have to sincerely want that change.

And if you don’t think you have the power to stop? Then you make the sincere Viduy that you want to stop and put the rest on God. As Pirkei Avos says,

“It is not your responsibility to finish the task, yet you are not free to withdraw from it.” Chapter 2:21

Though we might fail, as long as we keep trying, that’s all that can be asked of us. But we have to be honest with ourselves and with Hashem. So if you really want to change, Yom Kippur has the extraordinary power to get us there. But we have to show Hashem we want it. If your thing is cheeseburgers, have you thrown away all the McDonalds coupons? Or do you still look through the newspaper for the Monopoly game pieces? Do you really want to get married? Or do you have Tinder still on your phone?

This is your opportunity. Get rid of the maybe factor. Get real. Honestly ask God to be free of it. The rest is up to him.

Have a meaningful and transformative fast.