Dealing With Doubts on the Teshuva Process

I recently read a D’var Torah that really spoke to me. Part of it focused on Devarim (Deuteronomy) 25: 17-19

“Remember what Amalek did to you on the road, on your way out of Egypt. That he encountered you on the way and cut off those lagging to your rear, when you were tired and exhausted; he did not fear G-d. Therefore… you must obliterate the memory of Amalek from under the heavens. Do not forget.”

It then brought us back to Shemoth (Exodus) 17:1-8, when the Jewish people just left Egypt and camped in Rephidim. There was no water to drink. The people questioned “Is G-d in our midst or not?” This was right after departing Egypt, after the 10 plagues, the miracle of the parting of the Reed Sea, etc. After such miraculous events, how could they question “Is G-d with us?” Moses is so annoyed that he names the place “Challenge and Strife.” Then, right after the Jews showed doubt in Hashem, the nation of Amalek attacked from the rear, picking out the weakest and destroying them.

Next, the D’var torah pointed out that the Hebrew word for doubt (safek) has a gematria, or numerical value of 240. This is the same numerical value for Amalek. And when words have the same value, it shows they are interconnected. Thus the fight against Amalek can also be seen as a fight against doubt.

For me as someone trying to become more observant, this is something I constantly face. Why do I try so hard to keep kosher? It would be so much easier for me if I went back to only keeping kosher in the home, but eating anything, or even just “vegetarian” outside the home. Why do I bother being Shomor Shabbos? Does it really make that much of an impact that I don’t check my email, or watch TV? After all, I survived for many years not keeping it. Why keep struggling?

And the biggest doubt of all. Why am I becoming observant at all? Is it really worth doing? Who the heck am I doing it for anyway? Does G-d really care what I do? Little ol’ me? After all, I’m just a speck in the grand scheme of everything.

The D’var torah ends by talking about how to defeat Amalek, and thus doubt. It points out that Amalek is irrational and counterintuitive. To overcome him, we need Faith/Emunah. It is not something we develop, but rather it’s something already inside of us that needs to be unveiled.

And subconsciously, that’s what I’ve been using most of the time to quell these doubts. I’m doing it because I’m seeing the truth in the Torah, and how it relates to all people, even little ol’ me. And if that’s true, then the Torah as a whole shouldn’t be treated as a “Chinese Menu” (e.g. I’ll take two from column A, and 1 from column B, I don’t need anything from column C.) I have faith that there is a reason for everything, even if I don’t yet know what it is. Seeing it spelled out, especially with the allegory of Amalek helps to strengthen my faith even more. Will I ever completely defeat doubt? Probably not. Like all epic battles, it’ll probably be one fought through the ages (at least until the Moshiach comes). But at least the tools to fight it off are more clear.

16 comments on “Dealing With Doubts on the Teshuva Process

  1. Mr. Cohen, you clearly misunderstood my post.You took the quote I put in the top of my post that the author wrote, and responded to that quote.The quote that I respond to in my post was not written by me – I’m responding to the listed quote.I already am shomer shabbat(happily so), thank you very much.

  2. In response to Tuvia (message 12):

    Experience has shown me many times that I find answers to my Torah questions, if only I continue to study Torah with diligence and persistence, and also take typewritten notes on what I learn.

    Sometimes it takes me 5 years, 12 years or 17 years to find an answer to a difficult Torah question, and the answers come when I do not expect them, and had long ago given up hope of finding them.

    Studying Talmud is important, but it is not enough: You must also study a wide variety of Midrashim, Mussar books, Halachah books, English language Hashkafah books, and even pay close attention to Torah articles in Orthodox Jewish newspapers and magazines.

    In response to Reuven Andreessen (message 13):

    Reuven Andreessen said:
    Why do I bother being Shomer Shabbos?

    My first answer:

    The Jewish Bible [Tanach] teaches the importance of SHABBAT observance 17 times: [1] Exodus 16 [2] Exodus 20 [3] Exodus 23 [4] Exodus 31 [5] Exodus 34 [6] Exodus 35 [7] Leviticus 19 [8] Leviticus 23 [9] Leviticus 26 [10] Numbers 15 [11] Deuteronomy 5 [12] Isaiah 56 [13] Isaiah 58 [14] Jeremiah 17 [15] Ezekiel 20 [16] Ezekiel 22 [17] Nehemiah 13

    My second answer:

    Every community of Jews that abandoned SHABBAT observance has eventually assimilated and intermarried and vanished.

    My third answer:

    Minor tractated of the Talmud, Avoth DeRabbi Nathan, chapter 26:

    A Jew who fails to observe SHABBAT will NOT merit the afterlife of the righteous [Olam HaBa] even if he excels in Torah scholarship and good deeds.

    I invite both of you to my Judaism web site:

    This group distributes quick quotes from Jewish holy books and short true stories of Orthodox Rabbis. There should be no more than 1 or 2 distributions most weeks.

  3. Tuvia,

    If you would like some very general advice which goes beyond your particular question(which others who are inclined can respond to), FWIW:

    (1) Find someone whom you feel comfortable talking too, who you feel is knowledgeable and sophisticated enough to suit your particular intellectual needs, but also empathetic enough to non-judgementally hear you out(and who obviously is hashkafically close to where you feel is aapropriate to be). Finding the correct person may require some work!

    (2) Brush up and study seriously some basics. Perhaps part of what is missing from some discussion amongst laypeople is a lack of broad grounding in basics in Jewish philosophy, Nach, and history. I’m talking specifically about accepted mekoros (sources).

    (3) There is always an indirect method of enhancing faith, and that is being involved in the experiential aspects of Torah and Mitzvos.

    (4) On a related note, there is a series on the 13 ikkarim called Credo 13, which aired on Canadian TV, and which appeares to be produced by R. Ben Hecht’s Nishma organization. It has different speakers discussing each principle ranging from a charedi rav and those of a similar background to orthodox academics .

    Someone over thirty might want to skip the parts of the college-aged boys and girls(separately) talking/playing games, as that aspect seems to be targeting a younger audience. I’ve only skimmed through parts of the 13 videos, but one part I enjoyed was R. Meyer Schiller’s very forthright and honest response to various moral questions(see video # 9 18:20, and 22:30).

    This is the link to Kosher Tube:

  4. “Why do I bother being Shomor Shabbos? Does it really make that much of an impact that I don’t check my email, or watch TV?”
    I heard something interesting in shul that demonstrates the impact of keeping Shabbat.A friend was telling me about someone who out of ahavas yisrael extended Shabbat tarrying from bringing it to a close saturday night.Why? Because of souls in gehinnom. On shabbat, those in gehinnom get a reprieve and are released for the day to return when Shabbat comes to an end.A tzaddik would extend his shabbat to relieve the suffering of those assigned a sentence in gehinnom.That brings new meaning to the significance of keeping Shabbat!

  5. I am in constant pain over the question of how today’s rabbaim state with certainty that the pshat of Torah from Heaven is a part of our mesorah and ikkarim.

    I am so upset that, as a modern person exposed to more than that ikkarim states, I have to somehow suffocate that part of me that believes “there is more to the story, much more” and just march on with this terrible sense that the ikkarim is, in its simplicity, not accurate, not real, not true, not supportable, not really even Jewish in a sense — too simple, too silly, too certain.

    We are born in the days far from the days of the originators of Judaism — WE simply don’t KNOW. I even find that Rambam himself was using pshat phrases to help the masses of his time — from all over the civilized world — hold together as Jews.

    And yet, the orthodox today affirm this simple ikkarim as the only truth. I come off as an apikoros.

    It is all so sad, and it is a kind of madness. The Jews are living in a kind of time of madness. And I live with them, and try not to go mad as I look to G-d to help me stay Jewish, and not take out on him what I feel is defective in the thinking of Haredi Judaism. G-d help us all.

  6. A question for the author of this post and the commentors:

    I struggle not with my emunah in Hashem, not with the belief that the Torah is truth, but with the actual laborious nature of Judaism. I personally feel bogged down by the minute mitzvos, the zman (time) constraints, the feeling like I’ll turn into a pumpkin if I am late for shobbas, G-d forbid. I will never get over the annoyance of a constricting shetiel. The list goes on. I understand we are instructed to be an Ohr Legoying and Kadoshim Tih’yu, but I could be that without worrying about so many of the little things. There are boundaries and then there is feeling suffocated. I try to have my emuanah and the seeing of daily nissim Hashem sends me be motivating factors, but it starting not to be.

    This might also answer the author of the “Norman” post where the author and a commenter are puzzled at how a person could believe in the Truth of Torah Judaism yet choose no to do it.

  7. Hi, and thanks for all the comments so far. Sorry I didn’t get to reply earlier, things have been busy. Anyway, Bob Miller and LC, thanks for your replies, you said it better than I could have articulated. And DK, one thing I guess I didn’t make clear is that I was talking about just for ME. I don’t presume to speak for, or to anyone else as to what they should do or how they should interpret things. (see

    yy – Thanks for the “before and after” reference, that makes a LOT of sense!

  8. DK said, “If you push the vast majority of world Jewry to the wall and demand all or nothing, you are not going to be happy with the answers.”

    AND ‘pushing someone to the wall’ and ‘demanding’ is very different from an acknowledgement that the ‘right’ thing is the ALL.

    There’s a vast difference between ‘not for me/I have a right to select which mitzvos *I* believe have value’ and ‘I will start with X and not Y because it speaks to me but I understand ALL to be something to strive for.

  9. DK said, “If you push the vast majority of world Jewry to the wall and demand all or nothing, you are not going to be happy with the answers.”

    Nevertheless, all Jews will ultimately choose to do exactly that—all. If we can help to persuade them (this is not the same as demanding), that day will come sooner.

    As the Aleinu prayer details, we look for the day that the other peoples of the world will sign on, too.

  10. DK-Actually, there are famous Talmudic passages which indicates that all of the nations of the world were indeed offered the Torah and rejected it because of their objections to a critical portion of the Aseres HaDibros or their inability to fulfil a simple and relatively easy positive commandment, namely Sukkah.

    Of course, Amalek represents the negative response to that committment which one can find in the writings of all critics of Judaism from Tactitus to Hitchens. More fundamentally, wnen one examines the universalist counter response, it degenerated into such utopian nightmares as Nazism and Communism.In a real sense, Amalek represents the continued rejection of the unique combination of the universal and the particular that constitutes Torah, Halacha and Mesorah.

  11. This was a great post. Doubt of the effect of mitzvos on ourselves and the world is a major factor in the current trend of adults either falling into the OTD category or issue of “Timtum HaLev”- a blockage/hardness of heart.
    It seems the current Yetzer Hara is to forget that there’s a constant battle.

  12. It points out that Amalek is irrational and counterintuitive.

    On some level, Amalek is the mirror image of the Jewish mission as well, which is in its own way, also irrational and counterintuitive in the sense of a particularist relationship with an activist God. In a more universal sense, the human condition defies logic and explanation. In fact, one could argue that Amalek is responding very negatively to a leap of faith that the human condition means anything at all, to the declared mission of Israel and the negation of that special mission, or any mission at all. The Israelite and Amalek positions represent the two extreme poles of human interpretation of why we are here.

    And if that’s true, then the Torah as a whole shouldn’t be treated as a “Chinese Menu” (e.g. I’ll take two from column A, and 1 from column B, I don’t need anything from column C.)

    If you push the vast majority of world Jewry to the wall and demand all or nothing, you are not going to be happy with the answers.

    Perhaps instead, we should allow for varying degrees of literalism that we and others attach to our respective theologies, as well as the cost of not recognizing any mission beyond our own egos and desires. While this might sound too fluffy for some, and many Orthodox frequently downplay the importance of non-Jews, I would note that the Torah does record varying responses of other nations to these questions that all of mankind face — or at least, should be grappling with.

  13. great message, I’m sure many can relate

    Some things that help me are remembering that every mitzvah I do brings positive spiritual energy that helps the world. And aveirahs(sins) bring damage. We might not notice that, but it happens none the less. – On a personal level, we have these mitzvos to help us connect to G-d. They might become routine after a while, but that’s when our new challenge comes to do it with meaning and joy again

  14. nice. Thanx for the humble simplicit. It’s a battle we must all wage. I for one can vouch that these doubts often resurface davka after one of those amazing Y. Mitzraiim experiences.

    As we say in tfilla: Ha’seir Satan m’lifneinu u’m’achareinu / may the Satan be removed from before AND AFTER us. It’s referring to Mitzvos. Before = all that stuff that keeps us from doing ratzon H’. After = those doubts that plague us once we’ve begun.

    One thing is sure. The Sages anticipated these conflicts.

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