A Few Thoughts About Heist Stories

Heist stories are interesting to read and can also be interesting and challenging to write, but they do come with a set of thoughts you should clear up before writing the story (especially hard for a discovery writer like me and, perhaps, the reason why I haven’t started Inez’ and Tom’s second adventure so far). Yet, I do like me some heist stories and there’s not enough of them around, if you ask me. So, here’s some thoughts on that matter.

First of all, make your main lead sympathetic. A lot of stories can do with a less-than-likeable main lead, but the heist story can’t. The main reason for this is that heist stories will challenge the audience’s morals. A heist is always a crime (usually a con or a break-in). If you want the audience to root for your main character while they’re committing a crime, you need to make the character sympathetic (it also helps if the other side is unlikeable or outright evil). In addition to being likeable, the main lead also should have a good reason for their crime.

A good example of that is the manga/anime series “Cat’s Eye” (see their Wikipedia entry) which revolves around three sisters doing late-night heists to assemble their father’s missing collection and, hopefully, finding out where their father has disappeared to and why. The sisters are not doing their heists simply for the money and they are nice girls overall, so the audience can feel safe, rooting for them. Both the personalities and the cause are a safe bet for the audience.

Second, despite the ultimate ending of the story, there should be trouble on the way. Like with every type of story, conflict (see my post on that) is essential for it to function. Heist stories often include finding the right specialists to pull a specific heist off. The main lead, no matter how good they are at their work, can’t do it all alone. Heist stories are team stories, not something for a single person to do alone. Even Colonel Clay didn’t do it by himself, he usually had help from his wives (yup, plural). And wherever more than one person is doing the work, mishaps happen. People can’t keep the timing, for whatever reason. People do things in their own time, which is not the same as that of the rest of the team. Someone makes a mistake (after all, the characters usually are human). And because of that, the conflict rises and the stakes go up.

This goes well with another important point. The main lead of a heist story usually has a mastermind personality, otherwise how could they plot such a complex plan? And masterminds are in danger of coming across as ‘too cool’ in the story. They usually expect everything and have backup plans for their backup plans. This talent, however, is not good when it comes to conflict, because the latter might fall flat, if the character can deal with it easily. On the other hand, your mastermind needs to be competent, otherwise it will look unrealistic for them to finally pull off that complex heist.

One way to do that is to have the bad things happen only for the mastermind to treat them as if they’d expected them from the beginning. That, however, can play into the ‘too cool for you’ problem and should be used sparingly. Besides - if the mastermind can deal with everything, how is the final heist going to be interesting for the audience? If the mastermind will always win, there’s no way the heist can go wrong, is there? But if a plan went awry before, perhaps even doing severe damage to someone or something, there is tension. Sure, audiences expect the hero to win, but there’s several different definitions for ‘win’ and that doesn’t mean all members of a team have to come out on top.

Another way is to make the conflict one on a personal level. Perhaps the mastermind needs to enlist the help of a person whom they hate - or who hates them. Perhaps they need to perform several jobs for those whom they wish to hire and those jobs are not exactly in their usual line of work. There are ways to take a mastermind out of their comfort zone as well, they just need a little more imagination. And a mastermind failing at something which, say, demands a specific skill outside of the mastermind’s skill set doesn’t make the mastermind look incompetent. It simply makes it clear that the mastermind is not a Jack-of-all-Trades - which means there is a chance they will also do something wrong in the actual main heist.

Then there is the other side. To make things harder for the main lead in any kind of story, the other side must always be stronger and better off. So whoever the main lead and his team want to steal from, they need to be able to afford the best security, the best technology, and the most ruthless minions. In the best case, the story boils down to mastermind versus mastermind, to a mastermind personality on each side. It boils down to a strange, real-life version of chess that way.

In addition, you have to juggle a group of people and their dynamics, it’s not just about the one hero and the side characters which assist. The heist will only work if a group of people works together, so there are a lot of interpersonal dynamics going on as well. It’s not just the ‘romantic interest’ or the ‘jealous best friend’ or the ‘friendly rival.’ It’s a group of people all of whom have their own motivation to work on this heist - past history with either the main lead or the enemy, monetary reasons, challenges they can’t ignore, personal feelings, and much more. All of the characters will need to get something out of the heist, will have their personal arcs to follow, so you as the author are looking at a team effort in more than one way there. The team needs to come together, the leader needs to smooth over ruffled feathers and deal with internal quarrels, the team needs to learn how to work smoothly together, and to rely on each other. Of course, you can have several leads in any other kind of story, too, but the heist story will only work if you have several leads working together.

Those are very much my thoughts on heist stories. They’re fun to read and can be fun to write, if you do a minimum of plotting yourself before you write them (even as a discovery writer).

Heist stories are interesting to read and can also be interesting and challenging to write, but they do come with a set of thoughts you should clear up before writing the story (especially hard for a discovery writer like me and, perhaps, the reason why I haven’t started Inez’ and Tom’s second adventure so far). Yet, I do like me some heist stories and there’s not enough of them around, if you ask me. So, here’s some thoughts on that matter.

First of all, make your main lead sympathetic. A lot of stories can do with a less-than-likeable main lead, but the heist story can’t. The main reason for this is that heist stories will challenge the audience’s morals. A heist is always a crime (usually a con or a break-in). If you want the audience to root for your main character while they’re committing a crime, you need to make the character sympathetic (it also helps if the other side is unlikeable or outright evil). In addition to being likeable, the main lead also should have a good reason for their crime.

A good example of that is the manga/anime series “Cat’s Eye” (see their Wikipedia entry) which revolves around three sisters doing late-night heists to assemble their father’s missing collection and, hopefully, finding out where their father has disappeared to and why. The sisters are not doing their heists simply for the money and they are nice girls overall, so the audience can feel safe, rooting for them. Both the personalities and the cause are a safe bet for the audience.

Second, despite the ultimate ending of the story, there should be trouble on the way. Like with every type of story, conflict (see my post on that) is essential for it to function. Heist stories often include finding the right specialists to pull a specific heist off. The main lead, no matter how good they are at their work, can’t do it all alone. Heist stories are team stories, not something for a single person to do alone. Even Colonel Clay didn’t do it by himself, he usually had help from his wives (yup, plural). And wherever more than one person is doing the work, mishaps happen. People can’t keep the timing, for whatever reason. People do things in their own time, which is not the same as that of the rest of the team. Someone makes a mistake (after all, the characters usually are human). And because of that, the conflict rises and the stakes go up.

This goes well with another important point. The main lead of a heist story usually has a mastermind personality, otherwise how could they plot such a complex plan? And masterminds are in danger of coming across as ‘too cool’ in the story. They usually expect everything and have backup plans for their backup plans. This talent, however, is not good when it comes to conflict, because the latter might fall flat, if the character can deal with it easily. On the other hand, your mastermind needs to be competent, otherwise it will look unrealistic for them to finally pull off that complex heist.

One way to do that is to have the bad things happen only for the mastermind to treat them as if they’d expected them from the beginning. That, however, can play into the ‘too cool for you’ problem and should be used sparingly. Besides - if the mastermind can deal with everything, how is the final heist going to be interesting for the audience? If the mastermind will always win, there’s no way the heist can go wrong, is there? But if a plan went awry before, perhaps even doing severe damage to someone or something, there is tension. Sure, audiences expect the hero to win, but there’s several different definitions for ‘win’ and that doesn’t mean all members of a team have to come out on top.

Another way is to make the conflict one on a personal level. Perhaps the mastermind needs to enlist the help of a person whom they hate - or who hates them. Perhaps they need to perform several jobs for those whom they wish to hire and those jobs are not exactly in their usual line of work. There are ways to take a mastermind out of their comfort zone as well, they just need a little more imagination. And a mastermind failing at something which, say, demands a specific skill outside of the mastermind’s skill set doesn’t make the mastermind look incompetent. It simply makes it clear that the mastermind is not a Jack-of-all-Trades - which means there is a chance they will also do something wrong in the actual main heist.

Then there is the other side. To make things harder for the main lead in any kind of story, the other side must always be stronger and better off. So whoever the main lead and his team want to steal from, they need to be able to afford the best security, the best technology, and the most ruthless minions. In the best case, the story boils down to mastermind versus mastermind, to a mastermind personality on each side. It boils down to a strange, real-life version of chess that way.

In addition, you have to juggle a group of people and their dynamics, it’s not just about the one hero and the side characters which assist. The heist will only work if a group of people works together, so there are a lot of interpersonal dynamics going on as well. It’s not just the ‘romantic interest’ or the ‘jealous best friend’ or the ‘friendly rival.’ It’s a group of people all of whom have their own motivation to work on this heist - past history with either the main lead or the enemy, monetary reasons, challenges they can’t ignore, personal feelings, and much more. All of the characters will need to get something out of the heist, will have their personal arcs to follow, so you as the author are looking at a team effort in more than one way there. The team needs to come together, the leader needs to smooth over ruffled feathers and deal with internal quarrels, the team needs to learn how to work smoothly together, and to rely on each other. Of course, you can have several leads in any other kind of story, too, but the heist story will only work if you have several leads working together.

Those are very much my thoughts on heist stories. They’re fun to read and can be fun to write, if you do a minimum of plotting yourself before you write them (even as a discovery writer).