This thought (along with demonic possession) has always confused me. Wouldnt Satan want you to feel really good after sinning, so as to make you want to sin again?
The guilt thing doesnt really seem to work in "Satan's plan". Would it not be God that wants you to feel bad for whatever sinful act you have just indulged?
Guilt can lead to depression, especially if you continuously fail at a task and continuously feel guilty. Guilt has its use in making us aware of sin, but it can be used against us if it drives us away from the forgiveness of God and causes us to want to "just give up" as it does for some. Since Christians must constantly be "getting up" after being knocked down by sin, Satan would want to load the Christian with so much guilt that she stays down.
On the other hand, some can have their conscience seared. This can also work against a person, as they will no longer take some sin seriously and they will be more easily persuaded to it. Unbelievers often use their emotional conscience as their only moral compass and so it would work to Satan's benefit to sear their conscience.
There is more than one way to skin a cat, you see.
Also as I mentioned above about possession. Wouldnt that act as a counter to Satan and his plans? Wouldnt a true possession be great wealth and happiness and powe to sinful peopler? If Satan want's to steal as many souls as possible, it seems like torturing these victims (in some cases, publically) would not be the best method to gain control and gain more followers away from God. No, possession seems more like God in a strange twist. I would assume that Satan is not stupid. He know's what he's doing. Why then would he want you to feel guilt at all? Is guilt not the natural response of a conscience? Satan, would want to destroy that conscience and make you feel just dandy after commiting terribly sins.
Actually, Satan would have to have a very distorted mind for him to know the power of God (far better than any of us) and yet to rebell against him. And Scripture never portrays sin or unbelief as rational. Scripture says "The fool" is the one who denies God (Psa. 14:1) and that their "foolish hearts are darkened" (Rom. 1:21) and that "God [gives] them up to a debased mind."
This doesn't mean that every thought or action is irrational or lacking intelligence (some clearly are), only that it is perverted and especially so when it comes to truths that are more directly related to God and honoring him.
C.S. Lewis, in his book
Perelandra, describes this rational/irrational character of Satan better than any I have ever seen, so let me quote some of his depiction of Satan which I think will shed light on this. But first, I'll set up what is going on so it's not confusing.
The book is about a man named Ransom who travels to another planet, Perelandra. On this planet he meets one other person, simply called the Lady. But soon he finds that he is not the only human from earth. Someone he knows, Watson, has also come to the planet. Watson is something of his enemy (explained in a previous book). But Ransom eventually realizes that Watson is possessed by Satan (it's not immediately clear). At one point when Ransom is alone he sees some dead frog-like creatures who had been tortured to death. Ransom follows the trail of dead, tortured frogs and the following scene is described:
"[Ransom] saw a man who was certainly not ill, to judge from his easy stance and the powerful use he had just been making of his fingers. He saw a man who was certainly Weston, to judge from his height and build and colouring and features. In that sense he was quite recognisable. But the terror was that he was also unrecognisable. He did not look like a sick man: but he looked very like a dead one.The face which he raised from torturing the frog had that terrible power which the face of a corpse sometimes has of simply rebuffing every conceivable human attitude one can adopt towards it. The expressionless mouth, the unwiking stare of the eyes, something heavy and inorganic in the very folds of the cheek, said clearly: 'I have feautres as you have, but there is nothing in common between you and me.'…
Around this point Ransom takes a step towards Watson but falls to the ground. When he gets up, Watson is nowhere to be found. But later he finds Watson talking to the lady. What's interesting is that Watson's speeches are brilliant. He is clearly far smarter than the Lady and than Ransom. Ransom can see that what Watson is saying is wrong, but no matter how he tries to show it to the Lady, Watson is able to counter it.
But whenever Watson and Ransom are alone together, Watson will not say anything. He simply calls Ransom's name over and over again "Ransom... Ransom... Ransom..." to annoy Ransom. Eventually, the following scene ensues:
"[Ransom] had full opportunity to learn the falsity of the maxim that the Prince of Darkness is a gentle man. Again and again he felt that a suave and subtle Mephistopheles with red cloak and rapier and a feather in his cap, or even a sombre tragic Satan out of Paradise Lost, would have been a welcom release from the thing he was actually doomed to watch. It was not like dealing with a wicked politician at all: it was much more like being set to guard an imbecile or a monkey or a very nasty child. What had staggered and disgusted him when it first began saying, 'Ransom...Ransom…' continued to disgust him every day and every hour. It showed plenty of subtlety and intelligence when talking to the Lady; but Ransom soon perceived that it regarded intelligence simply and solely as a weapon, which it had no more wish to employ in its off-duty hours than a soldier has to do bayonet practice when he is on leave. Thought was for it a device necessary to certain ends, but thought in itself did not interest it. It assumed reason as externally and inorganically as it had assumed Weston's body. The moment the Lady was out of sight it seemed to relapse. A great deal of his time was spent in protecting the animals from it. Whenever it got out of sight, or even a few yards ahead, it would make a grab at any beast or bird within its reach and pull out some fur or feathers."
Now on the one hand we might say that intelligence is not simply being smart or rational, but putting smarts and rationality to their proper end: truth. On the other hand, we could call such a creature as Watson (Satan) a very "intelligent" creature. It can use reason very well, but it doesn't use it intelligently. This is the rational/irrational dialectic of Satan and, indeed, of every unbeliever.