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Repentance Is a Trap

Repentance Is a Trap

The real way to do Yom Kippur


There was a time when people would spend every evening of the days before Yom Kippur (and especially just before Yom Kippur) pondering their sins, their faults, and just everything wrong, bad and crummy about themselves. They would cry and sob from their hearts, fall asleep weeping, and then they would get up the next morning with a pure soul to serve their Maker. They often did this on other days of the year, and it worked pretty good then too.

Nowadays, when someone ponders his failures, it almost inevitably leads to depression. When pondering a past sin, a person starts asking himself why he did such a stupid thing, remembers what a geshmak1 it was, and ends up doing more.

So what happened? Quite simply, the darkness got thicker. When you’re surrounded by light, it’s okay to stick your nose into a few dark corners—maybe you’ll find something valuable you lost in there. But when you live in a world with the lights dimmed and all the blinds pulled down, dark corners become black holes with relentless gravitational pull.

Pondering your sins, you may just come to the conclusion that you actually enjoyed them.

That’s why repentance is so darn dangerous nowadays. When someone calls me up and says, “Rabbi, I messed up! How do I repent?” I tell them, “Repentance? Stay away from that stuff! It’s hazardous!”

So they say, “But rabbi, what am I gonna do about this sin messup deal in my life?”

And I tell ’em, “Just start running towards the light.”

“But then I’ll never do the repentance thing, like it says in all those books, about deep remorse and weeping over your sins.”

“Right now, forget the remorse and the weeping. Just get past it! It’s a trap. It’s your nasty, self-destructive snake inside trying to take you for lunch. And you’re the lunch.”

“No, rabbi, no! I gotta repent!”

“You don’t want to repent. You want a replay!”

“A what?”

“A replay. Okay, I’ll explain: When your mind experiences something pleasurable, it’s programmed to go replay it again and again, until it rewires all its neurons, readies the limbic system and has the entire endocrine system on board. That way, when the associated stimuli turn up again, by sight, smell, sound or whatever, your entire visceral person is primed to lunge for it like a hawk.

“But you won’t let your mind replay this particular messup, because you know it was real immoral, bad and crummy. So your mind, being just as smart as you are—since it is your mind after all—comes up with a solution: It says, ‘I don’t want a replay. I want to repent.’ Well, you don’t. You want a replay. Nothing to do with repenting.”

And you say: “But when will I rip away all the ugly stuff clinging to me because of this lousy thing I did?”

The brain will do anything to get its replay. Even convince you to repent.

And I answer: “So don’t repent. Do teshuvah instead.”

“That’s what I said I want to do!”

“No, you said you wanted to do repentance. I’m telling you to do teshuvah. That means “return.” Return towards the light from which your soul originally came. When you are running towards the light, filling your life with more wisdom, more understanding, more mitzvahs; more joy, love and beauty; and the light is getting brighter and brighter, and you want to reach out and talk directly, sincerely with your G‑d . . .

“. . . that’s when it hits you that the crummy messup from the past is holding you back, like a useless backpack weighing you down, like a lump of clay in your heart, like a wall between you and the true place of your soul. That’s when a genuine, aching remorse overcomes you, just swelling up all on its own from the bottom of your heart. That’s when you scream, ‘Get off my back!’

“You look behind for a sec, throw that junk away, and fly ahead. That’s when you repent. But not until then.”

During the ten days from Rosh Hashanah until Yom Kippur, there’s a lot of light. Yom Kippur is the holiest day of the year. Don’t go wasting that away. Especially, don’t go spending the holiest time of the year dwelling on stupid things you did.

Why waste the holiest day of the year dwelling on everything you messed up?

Instead, reach towards the light. Feel the presence of an Infinite G‑d, Creator of all things, who awaits your return to Him, with love.

And as you return, let that messy, gunky stuff just fall away, never to come back again. ’Cause you’ll never want it back again, once you’ve felt the embrace of His light.

Today, only the children of light can rise.

See also Feivel Gets Stuck.

That’s Yiddish for “delicious or enjoyable,” but a much more geshmak way of saying it.
Rabbi Tzvi Freeman, a senior editor at, also heads our Ask The Rabbi team. He is the author of Bringing Heaven Down to Earth. To subscribe to regular updates of Rabbi Freeman's writing, visit Freeman Files subscription. FaceBook @RabbiTzviFreeman Periscope @Tzvi_Freeman .
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t.ed September 8, 2017

Thank you for taking a chain off my fetters Reply

Rick Miller La Mesa October 4, 2016

Rich and simple Wonderful. So well put. Trash all the past misdeeds, forgive yourself and be free and joyous in following the path G-d he laid out for you. Reply

nina Perth West Australia September 17, 2015

Agree with Tom (comments below) totally. The situations & people I have responded badly to ARE sometimes Re-run in front of me where Gd allows me to respond more helpfully rather than grumpily. The second time around.Sort of like a spiritual ground hog day?
They have been a gift from Gd those Re-runs.
Thank you Tzvi from Perth Australia!! Reply

Tom FRansen Chicago, Illinois September 26, 2014

Thank you! Thank you Rabbi Freeman very much. I am in the beginning stages of conversion from Catholicism - starting a Jew By Choice program at my local shul. And "repentance" conjures many self-loathing moments in my life of dwelling on my sin. An especially attractive aspect of Judaism is the absence of "original sin." This is yet another reminder of reasons I'm converting. This helped me a great deal. As I approach Teshuvah, my presumption was very sack cloth and ashes. And being prone to depression myself, I see why you think "repentance" is dangerous!

This was truly a gift. Thank you. Reply

Keith Raport September 25, 2014

Definition Rabbi,
You have given us an apples vs oranges comparison, or teaching. If you use the Biblical definition of repentance, which seperates it from remorse, you will see that repentance must be practiced and embraced in order to put us in right standing before our perfect, Holy and almighty God. Repentance is a turning from the way that might seem right to us (but leads to death), to His ways that are higher than ours and it includes a change of mind and a change of purpose. We forsake our ways and embrace His ways. We are instructed to repent moment by moment in our actions and especially our thoughts which so easily stray, realizing that we fall far short of God's Holy law in all areas. Only this type of repentance leads to God's unmerited favor, His grace, and in this way we Glorify and Exalt Him while humbling ourselves which further leads to His Blessings. Only repentance opens our hearts to a right view of Holy God and fallen man. Question; How does God account for our sin? Reply

Alma Lopez Hollywood, Fl July 29, 2014

A back trap Rabbi Freeman, thank you for sharing this meaningful thought with all of us, which I absolutely agreed, we go on in our lives with so many clinging things that we be rely realize, that can be a n old backpack, or a same hairstyle, an arregnent if a living room, etc. but why? Because deep down is a sentiment of guilt behind it that keeps rewinding in our brain, controlling and blinding the true road. After all what has been said, what I see in the word 'guilt' is the word 'galut' of course, a reflexion of the original language.
Blessings and victory for all the seekers of the eternal light.
Almah Reply

Scott Cunningham Boca Raton, FL August 22, 2013

‘Get off my back!’ Who is on my back? It is me on my own back from my past negativity. Can we be good all of the time? Probably not, after all we are just humans trying to correct and sometimes these corrections are from past life's. Taking responsibilities for our own actions is repentance. Blaming others will only cause more negativity and will bite you in the hind quarters someday. If you must weep then weep for those you hurt in your past but do not disparage yourself rather thank G-d your supernal parent for the discipline and move forward with a positive attitude. Reply

ruth housman marshfield , ma September 30, 2012

garbage hanging around I am responding to a comment above, and it's true, there is always something more, to deal with, more garbage to take out, and now we sort through our garbage to separate the recyclables and that is a good thing.

it could be, we recycle. In every possible way. And this includes coming back, as in the migrations of soul. So it could be, these Biblical people came back, and it could be, G_d has a massive story to tell about all of this, when it's time. Reply

Anonymous September 26, 2012

Repentance is a trap A new discovery, it is a very private matter between the penetant and our Father in Heaven... Reply

CV LA September 24, 2012

There are no tribulations without transgressions. I understand it but I feel like its just a good excuse. There are no tribulations without transgressions. We are prone to do sins but the repentance and even punishment is what will make you stronger.

If someone truly believes this and is willing to do real repentance, that is the only way he or she will be able to properly move on. Reply

Eileen Patterson Old Town, FL September 24, 2012

Repentance Thank you for the way you tell people not to dwell on repentance. In everyone's life there are mistakes, some big, some small, some very painful. These mistakes can haunt us and torture our souls keeping us from doing the right thing and doing the Lord's will. Reply

Kyle Holsinger Bettendorf, IA September 24, 2012

nice article excellent job rebbe. Reply

Thomas Karp New Haven, Ct. October 14, 2011

To Karen A very big 'todah rabbah' for your response, Karen; the positiveness of it being like food to my soul.

Of course, what Rabbi Freeman posted inspired me.

Allow me to deflect a large portion of your positive response his way (I'm sure you don't mind).

Once again, thanks. Reply

Karen Joyce Chaya Fradle Kleinman Bell Riverside, CA, USA October 10, 2011

Thomas Karp, what an AMAZING post. It is astounding how you managed to break this idea down into understandable metaphors. Thanks. Reply

Anonymous henderson, nv October 9, 2011

i love this i only read this after yom kippur..
now i cant wait untill next one, i am one who wasted my day in replay but never really got anywere with it.
thank you. Reply

Chanoch Brown Miami Beach, FL October 9, 2011

Teshuvah Rv Freeman, We are blessed to have you in this world and in our lives. God bless you for being you. It is wonderful to hear advice from the heart, rather than from the can. Shalom Reply

Liora Kalamazomm, MI October 8, 2011

freeing wonderfully written wisdom, rabbi!
thank you!! Reply

Anonymous Durham, UK October 8, 2011

looking up If you have realised that you are having a difficult time looking towards the light, you are halfway there. All I know is that if you mean to look towards the light, something within you IS doing just that, even when you can't feel it and darkness surounds you. Slowly, slowly that "something" will change the nature of the shaddows until the shaddows themselves light up. Reply

Karen Joyce Chaya Fradle Kleinman Bell Riverside, CA, USA October 7, 2011

G-d bless you all, and Rabbi Tzvi & family To have a wonderful New year blessed by Go-d as much as you are a blessing to us. Reply

Margaret Altadena, Ca/usa via October 7, 2011

The Joy of the Chashem is my JOY Thank You for an answer. Reply

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