So you’re enticed by the life of a pirate, eh? Want to go out and cause trouble, make a name for yourself, and at the end of the day know that you have a fantastic reputation and a huge pile of riches? Well, you’ve come to the right node. All we need to do is figure out what sort of a pirate you are, and we’ll be on our way.

  1. When I walk into a room, I want people to:
    • Gasp in terror and dive under tables.
    • Start whispering amongst themselves.
    • Totally ignore you.
  2. I’d like a treasure chest full of:
  3. The most important thing to my happiness is:
  4. All you need is:
  5. If I could get myself a pet, it would be a:
  6. I’m most at home:
    • On the high seas.
    • In a dark room.
    • Hard to say when I keep getting shuttled around the Caribbean like this.

Okay! Let’s see how you did! Depending on how you answered the questions, it should be obvious by now that you want to be either:

Let’s tackle those one by one.

Traditional Pirate

Note that these suggestions would also work for space-based piracy, although you’ll have to change some of the words around.

As is it when you start any new career, there are some things you’ll need. Specifically, these are a ship, a cool name, a cool outfit, and a reputation. There are several accepted ways to get started in the field, and several of them will help you acquire these goods.

The first way is to apprentice yourself to another pirate. The advantage of this is that eventually (if he likes you) you can inherit his ship and possibly even his name (see The Princess Bride). Even if you don’t, you’ll gain valuable experience and probably a pirate outfit in the process. Another way is to sneak on board one of the ships of some country’s fleet and quietly kill all of the soldiers on board. Although this will gain you quite a reputation (as well as a ship), you’ll have a hard time getting either of them back to port, as it’s difficult to sail a large ship all by yourself, and, in the case that you run into another ship, it’s more than likely that they’ll attack you should they realize the circumstances. One final way (although there are many others) is to secretly use family wealth to acquire a ship and a crew, although you’ll want to keep your past secret. Make up a good story, because nobody will respect you otherwise.

Now that you have your ship, you’ll need to come up with a cool pirate name and earn yourself your reputation. Remember that all of the best pirates have names mostly made out of adjectives and names for things associated with death (like blackness, evil, hatred, and John). Although it is tempting to try using a ‘the’ in your name, people are far less likely to dread the name of Timmy the Dark One than Darkmast. Remember that once you have your reputation, your name will stick with you forever. And speaking of reputation, there’s really only one way to get a good one: fighting and winning. A lot. Attack everybody you see for a while, then start forcing other pirates into non-aggression pacts and possibly into paying you tribute. Another option is to take advantage of an ancient curse; the only thing scarier than a pirate ship is a pirate ghost ship. Curses are getting fewer and far between these days, though, so short of a trip to the pyramids of Egypt, you’ll have trouble locating one.

You'll need to look and sound like a pirate. Nobody will believe you if you have a pleasant intonation and wear tasteful clothes. Remember that all of the most successful pirates wear jackets over poofy shirts, carry pistols and a sword, and have some sort of pet. Consider growing out your hair and developing a long, tangled beard. You want hair that looks like it's fighing a war with itself in order to escape from your face. Wear large boots that make loud clunking noises when you walk. Develop a piratey way of talking, and make sure that you use all of the classic pirate words, such as "(Y)Arrrgh!", "Ahoy!" "shiver me timbers", and whatever else you can think of. You can practice by going into port towns, drinking yourself silly, and starting up a raucous conversation. If people believe your new way of talking, they'll beg to join your crew. If not, they'll start telling jokes about you.

There are a number of good pirate reputations to cultivate. These include, but aren't limited to:

  • Mastery of the sword
  • Mastery at naval combat
  • A liver of forged steel
  • Lack of mercy
  • Being a ghost
  • Being able to outrun any ship on the seas
  • Being a true connaiseur of booze
  • Ability to get shot many times without dying
  • Getting strength from a deal with Satan

It’s never too early to start thinking about retirement. A good option is to acquire yourself an island. The advantages are many, and include building up your reputation still further, ease of defense, seclusion, and (should you take care of the goodwill of a monarch) pretending to reform and becoming the governor of a new colony. Try to find an island in the shape of something, such as a skull. Make sure you find yourself a successor, as it’s a lot more likely that people will confuse you and arrest him. And who will believe it when the Dread Pirate Daggergleam starts claiming that he’s not really who he is, despite the ship, the crew, and the hold full of gems? That’s right, nobody.

Modern Pirate

Before we get started, we’ll need to have some wheat-from-chaff separation.

  1. Do you think there is more than one Internet?
  2. Does your e-mail address have “” at the end, or the semiword “gurl” in the middle?
  3. Do you use any of these words in online conversation while not in an attempt to be ironic:
  4. Do you have trouble conversing online while using punctuation, correct spelling, semi-correct grammar, and no abbreviations?
  5. Would you like totally never buy a computer from anybody but Windows because they obviously make the best software for reasons that you’re at a loss to substantiate on?

If you answered “yes” to any of those questions, then you should be aware of the fact that you will have great trouble getting anybody to take you seriously, and will have to go through a fair amount of reëducation before you can get started.

It’s important to come up with a good handle to use online. This way, people can refer to you by it without ever having an inkling of who you are, but while still being aware that you have a web of control stretching the length of the Internet. The following words are not allowed in pirate names:

Now it’s time to consider how and where you’re going to perform your work. Although one can (in some cases) perform one’s best work with a really nice setup in a nice house, it’s good for your image if you’re either leeching off of somebody else’s Internet connection, if the only thing of any value in your residence is your computer and attached peripherals, or if you’re so devoted to your work that you never sleep.

Be careful about how you work. Although it’s tempting to share with the world that which you’re pirating, you’re only hurting yourself, as either your stuff is so bizarre and obscure that nobody would want it, or popular enough to attract the idea of industry guard dogs. This is no good, unless you’re already dead and therefore unlikely to attract legal action (note I say unlikely). Better to share several gigabytes of read-mes, the complete works of several dead, prolific and moreover uncopyrighted authors, and your grandma’s recipe collection. Note that adding in extra spacing and increasing the font size by a lot will increase the size (and therefore perceived value) of what you’re offering.

Never use a mainstream client for your work. Remember that you’re a dark, dangerous underground pirate. Therefore, you should also have some coding skills. Write your client yourself, and make sure to use a badass unknown programming language that lends itself to unreadable code so that you can show it to your friends online and impress them. Give it a name that suggests evil, fell magic, or chocolate.

It’s also important never to actually use the goods that you pirate. If you recall, you’re doing this for the adrenaline rush, not for actually having the stuff. Someday you’ll wonder why you filled a terabyte or two with programs and music that you never ended up experiencing, but that day isn’t for a while.

Make sure that you have a good outfit. Appropriate items include black clothing, propellor beanies, a beer hat full of espresso or Jolt, and several stuffed animals. Preferably badassed ones. Give them dangerous-sounding hacker names, and bring them up in casual conversation online as if they’re dangerous hackers with whom you converse and often work. Do some research first, though: if you manage to tread on the toes of actual dangerous hackers whose names you’ve accidentally misappropriated, you’ll be in a world of pain and hard drive failure. So be careful.

Guybrush Threepwood

Really, there’s not much to keep in mind here. Be cool, and everything will be cool. There's a guiding force of sorts keeping you out of trouble. Rare are the situations in which your life is actually in peril, and some out-of-the-ordinary bungling on your part is required actually to kill you. Just remember that the more famous you get, the less likely that anybody will believe who you are.

No matter what sort of pirate you are, just keep your wits about you. People respect you. Perhaps some don’t respect you as much as they respect ninjas, or maybe robots, but you’re still something that children look up to and want to emulate. Your reputation is your biggest asset. You can always plunder another ship, but once word spreads that you lost a battle to somebody named Skip, it’s all over. You’ll never get a crew together again. So keep your heard, don’t do anything stupid, and if all else fails, get your crew to wander from port to port spreading rumors instead of actually doing anything.

For further reading, try:

And always remember, grog is made by mixing rum, sugar, and lime juice. No matter what you're told, mixing salt water and rum will not produce grog.

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