Being a scoundrel is a tough thing.

On the one hand, it can be defined as doing bad things. That’s certainly a component of a scoundrel, after all, but there’s often an undercurrent of respect. And, if anything, college is the time for testing those boundaries. You only live once, after all, and America sure loves its anti-heros. Think of Walter White or Don Draper — scoundrels, each and every one. Being in college is a safe spot to test your bounds of action.

1. Make a Scale

Some things are morally wrong. Some things you really want. The trick is to weigh those things on a scale and make your actions match it. For example: a characteristic of a scoundrel might be chasing after women. If the moral stakes are low- you’re just being a flirt- then you’re good to go. If the moral stakes are high- you’re engaged to the pope, somehow- then you shouldn’t do it. Easy, right?

Right. But don’t forget about you in this process. The greater good can often be the minor evil. If you really want to be with someone, for example, but they’re the ex of a friend’s-friend, get their number. Some of you might disagree: that is betraying a tangental bro, so to speak. But if you really like the girl, then that shouldn’t bother you. It’s a minor evil, sure, but if you come into it with an open spirit, that’s the greater good.

2. Think Ahead

Will doing whatever you’re doing make you (or anyone else) feel guilty or sick? That’s a major concern. Some people just aren’t cut out to be scoundrels. I’m one such guy- I get queasy with nervous guilt over the smallest things. I once called in sick for high-school and was so nervous and guilty I actually made myself sick. I can’t be a scoundrel.

But, like anyone else, sometimes I should be. There have been times where I still kick myself for doing the “right” thing- not taking a three-day weekend trip just because I’d miss a class, not skipping a reading so I could go to a birthday party, or not asking a girl out because I heard my friends’ friend had a crush on her, so I should just back up, bro. The opposite of guilt is regret of the undone and it’s just as powerful. Weigh those two factors and see what you can do.

3. First, Do No Harm

Any scoundrel activity you do engage in should be you-specific and it shouldn’t run the risk to harm anyone else.

An example? Changing the font on your periods for your essay would suffice, or emailing a fake attachment to buy you time to write a better paper. That’s cheating, and that’s a scoundrel’s move. But, ultimately, it’s harmless and you’re the only one who could get hurt.

4. Second, Make it Good.

If you’re really going to commit to the occasional bad act, keep it sparing, and make it important. Is this girl that exciting or interesting? Is this party really worth bailing on a meeting you just set up with a friend? If it’s going to be a seedy move, it has to be worth the stigma.

For example: if I’m really hungry, I’ll eat my house-mates food. Often, I won’t replace it. That’s a scoundrel’s move, but I reserve it for desperate moments of desire, like when the Nutella and bread is right there and pizza is, like ten bucks. But I’d never just walk over and take that for my breakfast. That’s the same transaction but the stakes are lower.

5. Repent (Or Repent in Advance)

If you have to be a scoundrel in the moment, be a saint after. Buy the guy some beer. Apologize for the damage done. Buy extra Nutella next time you’re at the store and otherwise make it right. Sometimes it’s better to ask forgiveness then permission, but at least remember to ask forgiveness.

Or, y’know, just don’t get caught.