On Writing: The Heist

I love a good heist story. I love a group of competent (or even not) characters getting together, going over, here’s the target. Here’s why it’s impossible. Here’s what’s in there that we have to get hold of, so we’re going to do it anyway.

I love them, but I haven’t written one. I’m not sure I could be subtle enough when I set up the exploits… and given my usual genres, yes, I’d be the one setting them up. I tend to lean toward fantasy, even if it’s often modern fantasy. And this is one of those kinds of stories that’s easier to write in a modern “real-world” setting than either science fiction or fantasy.

In short, we already have a clue about what “normal” and “high security” defense measures look like, and what normal modern people can do. So when our law-bending (or breaking) protagonists show they have clever ways to get around these measures… it feels much more plausible.

In a fantasy or SF setting, unless the writer has done a lot of setup and background detail work, we don’t know what “normal” security looks like. Is every wizard’s library protected by anti-fire wards that can be exploited as a distraction? Is the space station’s secure databank hub protected by advanced genetic analysis, or the “antique” sneaker-net access? Unless we already know the basics, we as readers won’t be impressed by how thorough and scary the security is, or how ingenious the characters are to get past it.

…Then again, the problem with laying out the basics is that unless you have very solid worldbuilding for the whole story, you may make it very obvious where you’ve left weak points the characters can exploit. Sigh.

Though you can work with that. If there’s an obvious weakness – say, people have to access this database to do their jobs, so data has to have ways to get in and out – then the people in charge of the area should know there is a weakness. And have taken measures to mitigate the problem. Those countermeasures should be the real stumper!

And it helps if you’ve shown us through the story that your characters have, shall we say, certain skills. Knowledge, odd talents, a particular sideways way of looking at the world that lets them find and exploit vulnerabilities that don’t exist for anyone else. Things like, say, being able to hold your breath for six minutes and free-dive….

Why yes, I do advise checking out Mission Impossible for heist inspiration. The shows, both series, as well as the movies. Also Leverage. You might also check out Red’s Trope Talk on Prison Breaks; the dungeon itself is the villain! And a Prison Break is another kind of heist. You’re just stealing yourself out….

19 thoughts on “On Writing: The Heist

  1. I think the closes I’ve seen to a “fantasy heist” is more along the lines of a superhero setup where each character has their own gimmick power and they combine them to get around the defenses.

    That lets them pretend the cumulative defenses built over decades don’t matter because they never anticipated this exact combination of powers.

    They tend to fall a bit flat for me because in most cases they’re young and inexperienced, which means nobody has built defenses to stop them, but it also means they have no experience dealing with all the secondary issues that would come up by using their powers that way… so the story pretends there are no secondary issues.

    I mean, there couldn’t possibly be a problem with using the fire powers for an extended period of time in a confined space, right?

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    1. That reminds me that I’m behind on my Dresden Files reading. I think I’ve got a novel and…a half maybe? That I have but haven’t read. One of them being a supernatural heist book where Harry’s tapped to help a group of supernatural beings break into Hades’s vault.

      Should be fun to see what happens there given how competent Butcher writes the big players as being.

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      1. You’re going to really enjoy that one. My three favorite scenes, that stand out in my memory from all the other good ones in the Harry Dresden series:

        • Sue.
        • The doughnut.
        • A scene from that book.

        More I will not say, lest I spoil it for you.

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  2. If you’re going with something that involves Cyber Security it should be the bloated mess of procedures required to make something “secure” that is the greatest weakness. Today a normal person will have more passwords than a prison warden would have had keys at the turn of the century. This means that “best practices” are at best impractical, at worst impossible.

    And most of the “solutions” to those problems are themselves a massive weakpoint. Thinks like password vaults create a single point of failure for the entire security apparatus and might as well have the person using a single password for all their accounts which falls right back to the issue of best practices being impractical at best.

    Which means that if you’re doing a heist on a place with high tech security it’s imminently believable that the big weakness being looked for isn’t a high tech solution but a low tech one. A password book and a master key that circumvents all that security hassle because it is a hassle and if people have to deal with it day after day after day they’re going to develop short cuts to bypass it just so they can get to work instead of spending half their day in security checks.

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  3. One thing to consider in the heist? Is a truism in any security set up the people are always a weak point.

    Like that guard who props open the side door where he temporarily disabled an alarm so he can take a smoke break at the same time every night.

    Or the cliched “password on a post-it under the keyboard”. It is true a depressing number of times.

    So the heist could be exploiting the people who have to deal with this ‘unbeatable’ security system day in and out and making shortcuts for their convenience, or just boredom.

    Like the USAF missile officers who figured out with the right set up one guy can turn both launch keys at the same time. Not out any desire to, just because they were bored and there are only so many times you can reread the manuals while stuck in an underground bunker.

    So in many ways, the people on the inside already compromised the system, or know how to. And you crew needs to figure out what those people know.

    And hope that security guard didn’t pick that night to go on the nicotine patch…

    OTOH a safety/security audit is a great way to get people to let you through. Clip boards are great social camouflage and asking to be let through because this part of the security is working properly “for a change”, handles the rough parts.

    Though in this case the loot has to be something you can slip into a pocket or briefcase, such as a disguised thumb drive.

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    1. Password on a post-it – oh yeah. When an organization makes you have an extremely long password, and then expects you to be able to input it on two vastly different devices so you can’t rely on muscle memory on the keyboard – argh.

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      1. Yep. It’s reached the point where the most secure password storage method is actually a pocket notebook. It’s on paper which cannot be accessed by hackers which are – now – the biggest threat to security so something that isn’t stored electronically is more secure.

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    2. I know a guy who was able to waltz through an off limits section of a hospital (he wasn’t an MD, he was there to see/help a hospitalized family member) by 1) having an ID on a lanyard like the rest of the hospital staff (the card of which he kept in his shirt pocket to hide that it wasn’t a hospital ID), 2) knowing doctor lingo, and 3) knowing one of the doctors in the hospital, who he was able to name drop about his “order of business” to get people to leave him alone.

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  4. All the examples of heist type fantasy or scifi stories I can think of are kind of … well, like Beach Episode. You have to get the world really built up, and then it’s more about the team you’ve been shown than the known challenge.

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    1. Any type of serial media (especially episodic serial media rather than long-form drama) very quickly becomes about the characters in a given world setting. Once a group of characters gets established as “likable”, the audience will be willing to see them in a whole bunch of situations just to see how they deal with it. This is especially true with characters that have matured *enough* that they can be the ones mentoring the “character of the episode” to mature. It doesn’t work as well with characters that obviously need more character development in a specific area. Those characters do better with longer media.

      Episodic serial media is a lot like a short-story collection that happens to the same characters in the same setting. So the goal has to be rather short-term in order to be solved in one. Something like a Heist works very well for that kind of thing.

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      1. Long-form drama hits the problem that was diagnosed by Aristotle: a work of art must be small enough that you can hold it in your mind as one thing.

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  5. I do remember a fantastical heist novel I read. I’d have to dig out my Kindle to be able to remember the title, but I recall it being pretty good. My favorite was the one character, the innocent naïf dragged along due to circumstances, and the heist leader deliberately sent him to the dangerous jobs. Because she’d figured out fast that he had a mystical protection as the object of a prophecy, and he hadn’t fulfilled it yet. Destiny wasn’t going to let him die until he had, and his presence allowed the success of those parts of the heist.

    It worked! And you even don’t question it, because the ‘object of prophecy’ reveal doesn’t happen until towards the end. But it was well played! Some things you accept as being part of the genre, nothing suspension breaking. But, yeah. A high fantasy heist.

    Found the title! The Palace Job by Patricia Weekes.

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  6. On the prison break-as-heist, sometimes the direct approach is best. How do Viola, Jaro, and Bianco of the Desert Alca Valino Gang in *Zoids: Chaotic Century* bust their leader Rosso out of prison? They attack it in their zoids, blow a hole in the wall of his cell (after he overturns and ducks behind his bed), drop him a ladder, and high tail it out of there.

    Direct, explosive, and it gets a young viewer’s blood pumping for sure.

    Granted, they do their best to be a little more subtle about their next heist – kidnapping the ten-year-old Imperial Crown Prince. At least until the assassins show up, that is. Then Rosso and Co. go in louder and messier than planned because delaying the assassins meant making noise that would get the guards in a tizzy….

    :snerk: And speaking of kidnapping heists, Hawkeye “kidnapped” (rescued) Wanda from Avengers’ Compound in *Civil War* by distracting Vision with an explosion in the yard….

    In short, when finesse doesn’t work, make noise! If everyone’s running toward that, why would they be looking for you? 😉

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  7. I was thinking. . .

    There are Master Thief fairy tales, which, on reflection, are relentlessly mundane. Then again, there are the Small Boy Steals From the Ogre, which are not. The hero is, but the target and treasure aren’t. Then, there was no way Jack could have learned that the harp would scream for help once stolen.

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