Bending The Rules: When Are Loopholes Evil?

Bending The Rules: When Are Loopholes Evil?

Evil comes in many forms — some less obvious than others. Today, we want to talk about a tricky kind of evil: when are loopholes, exploits and “gaming the system” OK?

Photos by Tina Mailhot-Roberge, Lenore Edman, JD Hancock, Daniela Vladimirova

What Is “Loophole Evil?”

Bending the Rules: When Are Loopholes Evil?

The rise of evil life hacks has led to a lot of straight-up unethical claims disguised as tricks: “Rob a bank to get more money for free!” Loophole evil, on the other hand, is far more of a grey area. Loopholes come in many forms: you could “gaming the system” to use the rules to your advantage, or “exploit the system” to take advantage of hole or weakness in the rules. Loopholes can come in varying degrees of evil, too — some would claim those exploits are worse than gaming the system, but it all depends on your perception whether any of them are truly evil or not.

Take 7-11’s Free Slurpee Day, for example. There are quite a few loopholes you could use to get more than your “share” of free Slurpee. You could game the system by flipping the Slurpee lid upside down the cup to create a bowl of bonus Slurpee. You’re still receiving just one free Slurpee, but you’ve found a creative way to make that one Slurpee contain so much more.

Alternatively, you could go a little further and visit every 7-11 in town to get free Slurpees until you puked blue. There’s no way for every 7-11 employee to know whether you’ve had your one free Slurpee for the day, so you exploit that loophole to consume an awful lot of Slurpee.

Are either of these evil? Are both of them evil? It will depend an awful lot on who you ask.

Why We Look For Loopholes

Bending the Rules: When Are Loopholes Evil?

The internet makes it easy to find loopholes of all kinds, and most are hard to really define in terms of good or evil. This is “the grey side”: the area between the dark side and the light side, and it’s where we push the limits to see what we can come up with. But why do we try to game the system? Because we can, for one, but there’s more to it than that:

Bending The Rules: When Are Loopholes Evil?
  • Laziness: Humans are like electricity. We will always look for the path of least resistance. We love to find the fastest, most efficient ways to do things because we like to be as lazy as we can. There’s nothing wrong with that! Laziness isn’t inherently bad, especially when it drives you to find a better way of doing something.
  • Free stuff: Why spend your hard-earned cash on something when there’s a way to get it for free? Of course, nothing is ever truly free, but regardless, we enjoy the rush of receiving something without handing over money.
  • The unfairness of an existing system: It’s illegal to rip a DVD, but it’s hardly immoral if it’s for your own use and you’ve paid for it. Sometimes the rules are there to prevent bigger problems, but they impede on our own personal uses.
  • To fix an existing system: Using a loophole to exploit a game or computer system can be bad, but it’s also how vulnerabilities are fixed and prevented. The best way to fix a network’s security, for example, is to demonstrate how you can access it.
  • It makes us feel smart: We like to think that we are terribly clever. In fact, sometimes we may use a loophole just to show others that we know about something and they don’t. We want to be smarter, and using loopholes makes us feel like we’ve outsmarted the system.
  • We don’t like to be told “no”: Human beings are curious creatures and we like to push the limits. It’s the reason we keep breaking world records, explore further into space, and the reason we hack.

We live on the grey side because we know deep down inside that rules don’t always equal right. Most loopholes can be justified one way or another, but it really comes down to your own personal ethics. Everything isn’t just black or white and the world is not divided into good people and bad people. We’re all just people and we exist in the grey space in between two ideals. We may not always know if what we’re doing is right, but there’s a place in this world to flex our evil muscles. Sometimes we don’t know where the line is until we go looking for it.

Where Do You Draw The Line?

Bending the Rules: When Are Loopholes Evil?

It’s really important to consider the consequences no matter how minuscule they may seem. The consequences of using a loophole may not affect you, but someone will be affected in some way. In that regard, perhaps the best way to look at loopholes is by exercising the enduring “golden rule.” Imagine how you would feel on the other side of your loophole use. In our world of anonymity it’s easy to think “it’s their problem, not mine,” but we are responsible for policing ourselves. When it comes to using loopholes, here are some guidelines you may want to consider:

  • Is it breaking the law? It may be Evil Week, but it’s rarely a good idea to blatantly break the law. If there’s money involved or some sort of profit at stake, it may be illegal, and getting caught has more serious consequences than just breaking a simple rule.
  • Is it affecting someone else? Consider the fact that someone else might get in trouble because of your actions. Are you taking advantage of someone who can’t protect themselves?
  • Is it worth the trouble? You don’t want to do anything that could lead to you losing your job or losing privileges.
  • What would somebody you respect think of you if you did it? Think of the one person you have the highest respect for. Would they be OK with what you’re doing?

Loopholes in any system, agreement or rule set can most definitely be used for good, but taking advantage of them in an evil way can lead to the dissolving of our moral fibre. So feel free to explore, bend, break and crack, but always think before you take action. You are responsible for the construction of your moral character, and just because you can get away with something it doesn’t make it right.

Lifehacker’s Evil Week highlights the dark side of life hacking. How you use that knowledge is up to you.


  • Pizza hut once had a cheap pizza deal docket they sent out online. It had no expiry date on it. I’m keeping that so I can get cheap pizzas when I’m an old geezer and they cost $20 each. I’ve used it several times and they’ve honored it.

    Domino’s used to but they local place is completely staffed by Chinese students now and they get confused. I couldn’t get an answer from the domino’s PR people on their Facebook page either. They all used to advertise that they would accept competitors vouchers. Maybe they just stopped.

    My favourite loophole was some guy who got busted for growing large amounts of marijuana. Since it was known what he did, he claimed all his expenses on his tax as business expenses and there was no law against it. It was closed pretty quickly after that.

  • Evil tip: When there is no sign or guidance from the establishment you are in, standing in line is a social convention, not a law.

    Westerners are so indoctrinated into standing in lines, they often can’t see other, perfectly valid queuing models. You’d think some people want to stand in line, they seem to just find opportunities to do it.

    Next time you see a line, or one person being served, don’t be a chump and perpetuate this convention by standing behind the last person – change the queuing model from a line to a crowd, and stand next to the first person in line.

    • The social convention being so strong in the first place means that you will be policed by the rest of the people standing in line, and often by the people at the register as well. Best case you’ll get abused by the other customers and refused to be served, worst case you’ll be punched.

    • That ‘social convention’ is very much alive at bars and clubs, and it is so much worse than lines!!!!

  • Standing in line is what we do because it is the fairest que. First person is at the front, last person at the back. How else can you que and be fair other than a line? Besides taking numbers… but then that is annoying.

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