What does the Rabbi mean when he says that there will never be certainty, only probability?
Does that mean that I cannot be sure that a certain thing is the truth, but with respect to another thing I can be certain that one is right and the other false?
Or is there doubt even here too—that although one position is more probable, maybe the other one is still correct?

I didn’t understand the question. I have no certainty about anything, neither comparatively nor in other questions.

Meaning, there is always a possibility that the approach I identify as flawed compared to another approach is nevertheless the correct one?

So what’s the difference between that and absolute skepticism? You’ll never be able to find a real justification for holding any particular approach.

Indeed, when I say that X is not certain, I am thereby saying that it is possible that “not X” will turn out to be correct.
But “possible” can be understood on many levels: 10%, 35%, or maybe 90%? When I say that X seems correct to me, that means that in my view there is a high probability that it is so. Therefore, the chance that I will turn out to be mistaken is small, but of course it exists.
The mistake of our postmodernist cousins is that they identify uncertainty with doubt. But that is not so. Lack of certainty indicates that it isn’t 100%, but there is still room for probabilities at different levels. I’ve written books about this, and you can read in more detail in Two Carts and In Truth, Not Stable.

I think the Rabbi means to take a practical approach. Either you make an effort and get as far as reality allows you to get, or you decide to be skeptical and remain with improbability in your hands. The Rabbi uses the principle that “the Merciful One exempts one who is compelled.” There is no way to solve the problem of certainty. But at least we can solve part of it—that is, the probabilistic part. And that’s something too. But if you didn’t make an effort, then you aren’t reducing the percentage of error. Did you make an effort? You reduced it. It’s more likely that you hold the correct view. In absolute skepticism, it doesn’t seem to me that anyone is comfortable with probability. One who holds the approach of absolute skepticism seeks absolute certainty. But since that is absolutely absent, the resulting state is skepticism that will always remain, and therefore it is absolute. But those who are not looking for absolute certainty and are satisfied with probability, for whatever reasons they may have—what seems to me to be the Rabbi’s point is that otherwise chaos would reign in the world of thought, and we could never have a discussion, because I present a doubt and you present a doubt, and the discussion can never be resolved and has no purpose. In short, in my opinion this is a question of approach: what goal are you aiming for? Certain theoretical knowledge, or practical probabilistic knowledge?
Honored Rabbi Michi, what do you say? Did I manage to understand you this time?

Oops, embarrassing—the Rabbi had already answered. The page didn’t refresh for me when I commented.

It seems to me that you definitely understood.

Thanks in any case 🙂

*A small appendix—certainty*: Why is the working assumption of most of the discussions here that it is impossible to reach 100% certainty? Because human thought has matured. A person who sees a tree with green leaves and a brown trunk may think that this is how the tree looks—but that is not the case, because if a dog comes along (which does not see the color red) or a bee (which can perceive colors that the human eye cannot), then they will see the tree in different colors.
This is true regarding everything that a person relates to (that is, everything with respect to which a person acts).
Let us now introduce two new concepts—1. Essence: the thing in itself (in the example, this would be the tree as it really appears).
2. Attribute: the description of the thing—how I see it (in the example, the human, the dog, and the bee will each have a different attribute/description of the tree).
Everything in reality has an essence (which is not exactly something belonging to the thing, but the thing itself) and an attribute (that is, manifestation—the relation to things external to it).
A person can (and perhaps must?) cast doubt on everything, since he never encounters the essence of the thing, only the attribute.
Let us expand a bit regarding the attribute:
A. There is pizza.
B. There is a person.
The person eats pizza.
C. There is “tasty.”
Is “tasty” found in the pizza itself? After all, another person may come along for whom the pizza is disgusting. Is “tasty” found in the person? After all, if there is no pizza (or other food), there will be nothing tasty for the person?
That is, “tasty” is a property created from the encounter of the pizza (object A) with the person (object B). “Tasty” is an attribute.
Now one can understand that everything a person experiences is an attribute and never the essence.
All this is true regarding everything to which a person relates by means of his tools for perceiving reality.
And now let us formulate a law (or perhaps this law is two laws?).
Everything to which a person relates is by means of the tools the person has for relating—senses, emotion, intellect, etc.—and therefore all a person has is only a relation to things, but the person never has the things themselves. (Since the thing is perceived by means of a certain tool, if the tool changes, the input changes—that is, if we relate to a child by means of sight, we will say he is beautiful, and if we relate to him by means of emotion, we will say he is beloved.)
Therefore there is doubt. It is like a room with six windows—one red, one purple, one green, etc.—and someone inside the room sees six rays of sunlight in different colors. Obviously what he sees is not the reality outside the room; he sees only the reality as absorbed through the windows.
However, there is something more. The person looking at the tree (from the first example) sees the tree as brown and is not sure whether the tree is really brown or not. What is he sure of? He is sure that he sees the tree as brown. It is 100% certain that at this moment, when he looks at the tree, he sees it as brown. (It may be that if his eye were changed he would see differently, and if the wiring in his brain were changed he would see differently, but it cannot be that right now he does not see the tree as brown.) He has absolute 100% certainty regarding the fact that the way he sees the tree—the attribute of the essence in relation to him—is brown.
In the same way, a person is 100% certain that he exists. Just as (and this is not a proof or logical necessity) I experience the tree as brown, so too there is an “I” that experiences it. It is not the chameleon that sees it as brown, but I myself see it as brown, and that is 100% certain without doubt.
After all this, someone may come and say: I am not certain that I exist! Rather, the very fact that I raised a doubt about whether I exist proves that I think, which proves that there is an “I” (Descartes’ proof).
How can that be? Rather, a common mistake is the skeptic’s mistake. The arbitrary decision that if something has not been proven, then one cannot be certain of it, is the fundamental assumption (the axiom) of that way of thinking. But we have now shown that there is no need for that mistaken fundamental assumption. (In certain cases it is mistaken, but as we said at the beginning, regarding everything external to the person—which is almost everything—it is correct.)
Conclusion: I am writing these things because all these questions existed for me too, and I struggled with them. I did not arrive at these answers on my own; I received help from the rabbis at the pre-military academy where I study (and therefore I recommend to all the readers here who can—to go to academies and yeshivot and ask). Of course, I wrote a kind of summary of a summary of these matters, which of course is not enough and is not a real answer. The goal here is to open a door toward a new direction of thought that affirms a person’s life (both in the sense of confirmation/validation and in the sense of happiness and joy). It is really impossible to grasp the general idea from this post, so I would also ask people not to try. But yes, the purpose of writing this here (and therefore I ask this too) is that you should not despair—go learn and check and think and ask questions. The most important thing is to ask and not keep it bottled up inside. I very strongly recommend Ateret Jerusalem Yeshiva or its pre-military academy for these questions, but any academy/yeshiva is good.
Good luck.

Since you copied your message here as well, I’ll copy my response too:

It’s nice to see a student who enjoys and derives the maximum from the teaching of his rabbis and appreciates them. Even so, it is hard to refrain from commenting on a few inaccuracies in what you wrote:
1. If every statement we make is only about our perception of reality and not about reality itself, then when I hear your statement, as far as I’m concerned it says nothing. It only says that you see reality this way or that way, but not that reality itself is this way or that way. Why is that interesting? When you make a claim to me, your intention is not to describe your feelings to me, but to make claims about reality. So there is no basis here for certainty, apart from certainty about your own feelings, which is irrelevant to me. On this topic, I highly recommend the beginning of C. S. Lewis’s book (the one from Narnia), The Abolition of Man.
2. When you say that there is God, or that the people of Israel left Egypt, or that the Torah was given, are you actually not making a claim about the world, but only about your feelings? If so, I wouldn’t count you for a prayer quorum. You’re an atheist with religious experiences.
3. When you see an object as red, the color indeed exists only in your consciousness. But that does not mean that maybe the object’s color is something else. It simply follows from the fact that the object as such has no color (or at least there is no reason to assume that it does). Color is a cognitive phenomenon. In the world itself there are electromagnetic waves. When a tree falls in the forest and there is no ear, no sound is heard.
4. Is your distinction between the thing in itself and the thing as it appears to our eyes (in our cognition)—which is of course the Kantian distinction between phenomenon and noumenon—itself only your feeling, or is it a claim about reality?
5. To sum up all the points: you are mistaken on your most basic point. The fact that our claims are mediated by our cognition is of course true, but one who is not a skeptic understands that after the mediation, there is still a claim here about reality itself. Notice that you, in light of your description here, are a complete skeptic. So it’s a little strange that you see your post as an argument against skepticism, or as something that answers skepticism. You yourself explain that all your claims are only about your own feelings and say nothing whatsoever about reality. That is the dictionary definition of skepticism.

All the best and much success,

Maybe I’ll sharpen things a bit (numbered according to your numbering, as a response to your claims):
1. Indeed, I am not trying (and it is also impossible) to prove something in a completely certain way, since every proof is built on certain axioms (for example, that our thinking really corresponds to reality), and therefore there is no certainty in proofs (the intellect is not certain). The skeptic assumes that in order for something to be certain, it must be proven, and that is not correct. In order for me to obligate you to think that something is certain, I have to prove it, but in order for me myself to be certain of something, I do not need a proof (for example, my own existence—and Descartes too had certainty in this from the fact that he doubted).
2. When I experience the color red, I am not claiming that the thing that appears red is red, but the fact that I experience it as red is absolute truth, that is “objective,” meaning 100%. I intentionally did not write about faith in God, in the Torah, or in the people of Israel, because the subject is still not sufficiently clear to me, and therefore I do not presume to speak about it. My intention was to show that there are not only chances (that is, doubts graded by percentages), but also 100% certainty, such that it cannot be otherwise. What that certainty means (for now we have only said that it exists on the existential level—meaning I am certain of my existence without proofs).
3. Is there no red in reality? Not sure. We do not have reality from its own side. What you said, that there are electromagnetic waves and so on—that is still not reality itself, but only how reality is perceived in our cognition through sophisticated instruments. Like in quantum theory: if you look with one instrument you see a wave, and if you look with another instrument you see a particle. That is, the tool changed, so the picture of reality we see changed. (Tools like a microscope and so on are like additional senses or refinements of the existing senses, but they still do not show reality as such.)
4. It may be that reality is indeed perceived through our tools, but the point is that we have nothing except what is perceived through our tools (especially since experience shows that with more sophisticated tools, the perceived reality changes, as in section 3).
5. I do not understand why the claim is about reality itself. From what I understood (it may be that I simply did not understand), you only said that this is so, but you did not explain or show that this is so.
In addition, I am not a skeptic, because when I say that I exist and that this is true, that is a claim about reality itself (namely my reality, but I really do exist).

I can’t conduct a discussion at such intervals.

Thank you very much, Rabbi. I really do think there is much more to delve into (and what you call mysticism in many places, or a private conception of great Jewish thinkers such as Rabbi Kook, the Maharal, Rabbi Yehuda Halevi, etc., are not as you present them, and there really is a great deal of intellect and logic in what is called “Jewish thought”), but I cannot answer quickly, and therefore we probably will not be able to continue the discussion.