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How to Sin Successfully
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My dear Schnook,

As we both know, sin is an art, a way of life, a form of human expression on par with love in its depth and involvement. It is also, as is evident from my personal experience and from your letter, quite a difficult undertaking. Most people are so discouraged at the outset they must either convince themselves sin does not exist or live a life ever in fear of it. While I do not consider myself a professional sinner (and in fact, as every demonic devotee knows, there is something noble about the amateur, who receives nothing in return for his efforts but the opportunity to practice the craft he so loves), I am an experienced one. I think it is well past time I share some of my knowledge of this unholy pursuit.

It is disrespectful to dismiss an earnest human endeavor as simple, over-easy, or worthless, and sin is no exception. There are many people of a religious bend who seem to think sin lurks at every corner and will leap out at them if they stop uttering prayers for even a moment. These people should also be afraid of sneezing around paint buckets and producing Starry Night. In truth, what they are afraid of barely resembles the grand tradition of true sin. It is impossible to sin by accident. On the other hand, you have the unwashed horde of ne’er-do-wells who think they are pinnacles of demonic achievement. Your new group of friends, I am sad to inform you, falls into this category. If you will not exchange them for a worse crowd, I must at least show you their mistakes, that you may be guided down paths of true darkness all the rest of your days.

I have organized my thoughts into five categories, each negating a different iniquitous inaccuracy:

1. Remember Whom You’re Hurting

The neophyte transgressor must first focus on building, and only later on demolition. Start seeing your charity dollars, for example, not as “good points” or the mitigation of your “wrongdoing,” but as anti-sins. What is a sin? A poke in G^d’s eye. What is an anti-sin? The divine eye drops.

Most people tell a terrible lie, for example, and decide all of a sudden that they’re sinners. Pathetic. Where was your passion for morality ten minutes ago, when you called your mother for her birthday? You did not think of it as an anti-sin. The most you would call it was “being nice.” Maybe in your mind you got some points for your good behavior so you don’t have to feel so guilty all the time (more on that racket in section 2).

The problem here is one of imbalance. You can’t be an old man with candies one second and the fell spawn of Satan the next. This is giving yourself too much credit and taking yourself much too seriously. It is like thinking you can be a bad son to your friend’s mother. You just don’t mean enough to be mean enough.

We thus see that to be a sinner, one must have a conception of, and relationship with, G^d. I know what you’re thinking: “Why does everything always have to be about Him?” But if you don’t humor Him at least at first, even your best no-no will only ever amount to the sin of smoking weed — a victimless, empty, waste of time that sometimes makes you feel good. This is not how real men do things, Schnook.

2. Don’t Feel Guilty

One of the most prevalent misconceptions facing the aspiring evildoer is that guilt follows bad deed. Certain Jews, often ones that birth children, take it upon themselves to enforce this terrible lie (Q: How many Jewish mothers does it take to change a lightbulb? A:”No, don’t worry, I’ll just sit here in the dark.”). And it is a lie, a lie that lingers in the human consciousness like the smell of hot dog relish lingers in a Yeshiva hallway after the students do P90X.

Ladies and gentlemen, what is our goal? To sin. Not to mope about in a mental fog with dirty laundry piling up in our corners like so many dropped popcorn kernels (these sheaves for the poor!). Guilt immobilizes, and a sinner is nothing if not a go-getter. The lazy and mattress-bound try to convince themselves that their sleep is a war against G^d, but you and I know the truth. Inertia is merely neutral; guilt prevents excellence.

It’s really about self-respect, in the end. You don’t see the do-gooders laying about not helping little old ladies across the street. We can’t afford to lose this war.

Sin, dear Schnook, but feel nothing. Feeling is the burden of those you sin against. Don’t take it upon yourself.

3. Never Do What You Don’t Want To Do

I once encountered a helpless case (his words, not mine) who desperately wanted to join our foul ranks. He decided he was unfit due to his love of Anti-Sins and distaste for the vast majority of really good transgressions. Trying to teach him, I presented the hypothetical case of the do-gooder who does good even though he does not want to.

“Even more righteous!” babbled the noob. “The self-sacrifice! The dedication!”

After I slapped him about his jowly chops, I pointed out what is obvious to all us old-timers. Nothing real was ever done ’twas against the doer’s will. It is no great thing, and it is, in fact, quite sad, to force oneself to do good though every brain cell and heart string rebels against it. It is no great thing to sin without gusto.

“You seem to agree with me that only he who naturally enjoys the sin ought to sin.”

I slapped him again and explained that his error was not one of insufficient goodness (or badness), but one of an utterly mistaken understanding.

Once again, it comes down to just whom you’re aggravating with your crime. Just as no spouse appreciates flowers only provided to spite one’s nature, the Uniforce will hardly blink if you kick a puppy just because you feel it’s adorable and you love it. If, on the other hand, you foster a sense of how you delay G^d’s dominion on earth every time you do not sanitize the shopping cart handle, and enjoy the pain you bring the Creator with all your heart, you will have all of heaven in an uproar.

It’s the little things, Schnook, the little things we do to others. A mere sense of duty never destroyed anything worthwhile. Ask a hun.

4. We’re All Going To Hell

The concept of hell has been bandied about by both sides for millennia. Reams of propaganda on the subject fill the shelves of many a religion. Thousands live their whole lives fearing its flames (if they knew better, they would fear the Justin Bieber Accordion remixes and the prepackaged pastries). A rarer specimen wants to go there as the manly soldier aspires to battle, daring his enemy to test his resolve. All of the above people have something in common, and that is their stupidity.

For the hell-fearers, I have bad news: everyone goes there whether they want to or not. Hell is not optional. Hell is essential, a next step, part of any refined education, and certainly part of public education. No one manages to make it through life without some suffering, and the afterlife is no different. Yet somehow the hell-fearers have the gall to look down on hedonists. Let’s face it: a hell-fearer is a hedonist, a late hedonist, one who misses the good stuff now and finds it later in his sparkly afterlife.

Pain and pleasure are for the enslaved, Schnook. Stand for something real.

Which brings me to —

5. –But Who Cares

The other side of the story, the few people who want to go to hell. Not for suffering, you see, but for principle. These people are misled. They are like the do-gooders who look forward to heaven not for its delights but because their struggles will be vindicated. What a sad lot. As I’ve been saying this entire letter, you need not look to consequences, rewards, punishments, or others for justification of your iniquity. The professional does the sin for its own sake, for its inherent evil. The sin is not a means to an end, it is the end. I know what you’re thinking: what about the poke in the eye? Well, it’s a bit complicated, but suffice it to say, the sin and the poke in the eye of the Creator are one and the same thing! The creator can’t avoid it. He decided on G^dly revelation and gave us the unique opportunity to sin for its own sake.

It is so very shallow to look at a perfectly legitimate sin, e.g. some juicy gossip down at the watering hole, and say that its evil is proved by its severe punishment. The sin itself is evil, on its own terms. Hell has nothing to do with it, one way or the other. It is a distraction from our grand task, our high art, our noble mission.

May you perpetrate outstanding offenses,

Your friend,



Inspired “sort-of” by C.S. Lewis’s “The Screwtape Letters,” but it’s not really his fault. Image from Flickr.


Originally posted on Hevria.

Originally on Hevria repentance sin

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