Well, you can start by watching Ocean’s Eleven, and Ocean’s Eleven, and then Leverage, and then Burn Notice, and then The A-Team, and then Mission: Impossible, and then all the other heist stories like The Italian Job or Heat. Watch, read, uncover as many stories about criminals as you can from fiction to nonfiction to reading security analyst blogs. Read the spy memoirs, the thief memoirs, the fake ones and the real ones. Check out magicians, hypnotists, card tricks, and sleight of hand. Watch the making ofs and director’s commentaries looking for clues behind the thought process of these stories. The hows and the whys as you look into the research they did. Burn Notice, for example, is famous for using stunt props and technological rigs that work in real life. Like using cell phones to create cheap bugs on the go.
The worlds of criminal fiction and spy fiction rely on being able to present (or convincingly fake) a world which feels real. A heist is all about exploitation. So, you need a world with security structures to exploit. You’ve got to know how things work before you can craft a way to break them. Social engineering, hacking, and every other criminal skill is about breaking the systems in place. So, you’ve got to get a baseline for how law enforcement and security analysts work. What security systems are set up to look like. The ways we go about discouraging thieves. Better yet how people behave. Real, honest to god human behavior.
So, you know, pick somewhere in order to start your research. Get an idea of what you want write about stealing, then learn everything about the object, the museum, the city, the country, and its customs as you can.
If you’re setting a heist in a futuristic or fantasy setting then luck you, you get to make all of it up.
Learning the plot structure and conventions of the heist genre is the first step. This means watching lots and lots of heist movies, shows, and reading books. Over time, as you become better at critical analysis, you’ll begin to see specific story structures and character archetypes emerge.
The Heist Story is a genre. Like every other genre, it comes with its own structure, cliches, archetypes, plots, and genre conventions which necessitate the narrative. The better grasp you have of those, the better you’ll be at writing a heist.
For example, a heist story like Ocean’s Eleven relies on a collection of thieves rather than a single individual. The character types are as follows:
The Pointman - Your planner, strategist, team leader, and the Jack of All Trades. Can also be called the Mastermind. They’re the one who can take the place of anyone on the team should they fall through. They’re not as good as a specialist, but they’re very flexible. Narratively, he plans the cons and subs in where he’s needed.
The Faceman - Your experienced Grifter, here for all your social engineering needs. These guys talk their way in.
The Infiltrator - Your cat burglar or break-in artist. Basically, the conventional genre thief. Your Parker, Catwoman, Sam Fisher, or Solid Snake. The stealth bastards, they’re all about silent in, out, and playing acrobatic games with the lasers.
The Hacker - The electronics and demolitions specialist. Usually this is the guy in the van overseeing stuff remotely. Your Eye in the Sky. Their skill set can be split up and swapped around as necessary.
The Muscle - The one who is good at fighting. They’re combat focused characters, usually with mercenary and special forces backgrounds. Though, that’s optional.
The Wheelman - The one who handles the getaway. They’re your often overlooked transport specialists. It’s not just that they can drive, they’re skilled at getting lots of people around, figuring out how to move your valuables, and exiting hostile cities or countries undetected. They get the team in and they get them out.
For an example of these archetypes, I’m going to use Leverage. Nathan Ford, The Pointman (technically, he’s written like a Faceman). Sophie Devereaux , The Faceman. Parker, the Infiltrator. Hardison, the Hacker. Eliot, the Muscle. They all take turns being the Wheelman.
Other examples like Burn Notice: Michael Westen, the Pointman. Sam Axe, the Faceman. Fiona, the Muscle. They all take turns with explosives, Michael will invariably take all the roles during the course of the show.
Ocean’s Eleven has multiple variants of these archetypes, all broken down and mixed up.
You can mix and match these qualities into different individuals or break them apart like in Ocean’s Eleven, and more than one character can fill more than one role, but that’s the basic breakdown. For example, your hacker doesn’t need to be a guy in a van overlooking the whole security grid. One guy or girl with a cell phone can sit in the lobby of a building with an unsecured wireless network and crack the security. Welcome to the 21st century. The skills don’t necessarily need to take the specific expected shape.
What you do need is the basic breakdown: You need someone to plan the con, you need someone to be your face or grifter, you need someone to break in, you need someone to watch the security/electronics, you need muscle to back you up, and someone’s got to cover the getaway.
These shift depending on your plan, but this is the expected lineup for a heist narrative. The first step of a heist narrative is not the plan because we don’t have one yet. We’ve got an idea. Pick your target. Maybe it’s a famous painting. Maybe it’s a casino. Maybe it’s a rare artifact from a private investor’s collection loaned to a museum for a short period of time. Maybe it’s art stolen by the Nazis during WWII. Whatever it is, figure it out.
The next step is simple. If you want the thing, you’ve got to find a way to get it. This is a big job, your standard thief won’t be able to pull it off alone. So, you gotta go recruiting. Get your team together. Make sure to establish the goals of the different members for joining. Who they are. Their pedigree. One might be an old flame or an old enemy. This is where we lay out some character driven subplots.
When everyone’s together, we’ve got to lay out the plan. Before we have a plan though, we need to establish where the object is and the issues in getting it. Why this has never been done before. So, what are the challenges? Invariably, an object worth a great deal of money will have a lot of security protecting it. Figure out what that security is, who the item belongs to, what sort of retribution do the thieves face beyond what they might expect. Lasers, pressure plates, cameras, security, other career criminals, mob bosses, the rich and powerful, whatever.
After that: How do you get it? Then you’ve got to plan the con, while taking everything into account.
Then, We prep the Con. There will be steps to take before the con can be put into place, your characters taking their positions in plain sight. Stealing whatever pieces you need to make it work. Casing the joint. Etc.
Then: Run the Con. This is the part with the actual stealing. Better known as the first attempt. Things go well, there may be a few mistakes, but things are going well and then we…
Encounter Resistance. While running the con, something goes wrong, pieces fall apart, the thieves come close to success but the object gets moved and they suddenly need a new plan. New information may pop up, it may be one of your artists was running a con of their own separate from the rest. If there’s a double cross in the works then this may be when and where it lands.
We’re ready now, so it’s time hit up: Steal the Thing, Round Two. Your characters put their new plan into play and get about thieving the object of their desire.
Lastly: The Get Away. This is the part where your thieves make for the hills with their stolen treasure. This can be short or long depending on the kind of story you’re telling and other double crosses may occur here. It could be the end of the story or the beginning of a new heist.
Heist stories are like mystery novels. They’re all about sleight of hand and misdirection. You’ve got to keep just enough information on the table to keep your audience on the hook, and just enough information off the table to surprise them later on the twist. Yet, when they go back to re-read the novel again, they’ll find the answer was there all along. They just didn’t see it coming.
If anything, learning how to write a well-done heist or a mystery or any kind of novel in this genre will teach you a lot about how to manage your foreshadowing and create superb plot twists. Like any good con, you need to lay out all the conflicting pieces where people can see them, let them draw their own conclusions, withhold the critical context, and then hit them with the whammy.
Like lots of audiences, new writers (and even some old ones) can get distracted by the shock and awe. They see they’re impressed by the conclusion, not the lay-up. If you want to write any kind of fiction, you need to learn to see past the curtain and pay attention to the critical pieces leading into an important moment rather than the moment itself.
Good writing isn’t modular, you can’t just strip out pieces and run with them because you’ll end up missing the crucial, sometimes innocuous pieces that ensured the scene worked. Like the Victorian Hand Touch, every moment between the two leads and most of their scenes with secondary players are working for that singular instance of eventual, gleeful catharsis.
If you’ve got a plot twist coming in your novel, every sentence from the second you start writing is working towards it. You start laying out your pieces, funneling in your tricks, and playing with misdirection. You may have multiple twists, to cover yourself, divert your audience, congratulate them for successfully guessing your ploy, and reassure their initial suspicions before catching them again on the upswing.
The clever writer is as much a con artist as their characters. The only difference is the target of their con is their audience. The tricks in their bag are narrative ones, and they work with the understanding that it doesn’t matter if someone guesses the end so long as they’re entertained by the journey. A great story stays entertaining long after the audience has figured out all the twists.
So, don’t get caught up in Red Herrings and frightened about not being able to outsmart other people. Tell a good story with conviction and heart about a bunch of crooks out to steal their heart’s desire.
That’s all there is to it.
