How do you think about this kind of thing?

He knows too much.

Someone (an enemy or someone who he once thought was a friend) sets him up with the mob boss (perhaps to hide his own disloyalty).

The police are using him without his knowing it. They set him up in order to catch the mob boss or make him talk. "Hey, we can protect you . . . if you're willing to talk to us now."

The guy was once involved with the mob boss' girlfriend or wife (since he was ever close). The boss considered it betrayal.

The boss is testing the loyalty of one of his other lieutenants (or one he suspects of being an informer). This kills two birds with one stone.

Or . . . dozens of other possible reasons.

Those were just off the top of my pointy little head.

Put yourself in the position of the characters and their lives. Start with "being" the mob boss. What does he want (external and internal)? What are his problems? How does getting rid of your protagonist help him or solve a problem.

omg ...

Did you steal the idea from my stories? haha, I have a short fiction series, published in AHMM and EQMM in which the MC, who is female, is hiding from a criminal gang. She's in MA; the gang is in CA. The way she 'escapes' from them is by faking her own death, which is part of one of the stories.

But why do they want her? (Or why are they still a threat?) Because she was married to the gang leader, who is now deceased; however the brother-in-law would like to know where she is and what she's doing because she does 'know too much.' The only way to escape this gang was to die, hence she does, sort of.

In later stories this fear is always with her, that someone from 'there' will find her 'out here.' She's created an entirely new identity, with a fake birth certificate, etc. She tends to move around a lot, but finally settles on Cape Cod where she has a job as a caretaker for an author who summers on the Cape.

Anyhow ... it's a great idea. Put yourself in the guy's place - imagine yourself to be him. That's what I do, then create a predicament for the character and take it from there ...

(Oh, and one more thing: in my stories I added a small 'romantic angle,' and the guy she falls for is the only detective in the small Cape Cod town of Westfleet. Of course he's a cop. What else? )

Criminals, especially gang leaders, have fragile egos.

Your main character has wronged him. It doesn't matter how small or petty or nonexistent the wrong was, it's still a threat to his authority. It's personal, and he needs to assert his alpha male-ness.

Layla Nahar said:

So, how did you come up with all those things?

I think that might sound flippant. How can I put this question better? I'm hoping that the ways other people approach a problem like this will give me some ideas to solve it myself.

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It's called brainstorming. You might want to google brainstorming techniques but basically you just sit down and write up the possibilities - no matter how far fetched. Once you've done that you can start narrowing down your options based on the reality of your world and what fits your character's personality and motivation.

Whenever I'm stuck on story details and can't brainstorm anything satisfactory on my own, I chat with someone. Whether it's writing a blog post or talking directly to a writing buddy (usually over IM because I like to have my thoughts saved), it usually jostles something loose. With a buddy, I've got their input to help. They ask questions, give suggestions, and I'm left to find the answer for them. They can see things from a different angle that I might not have been able to see, or a suggestion doesn't work, but leads down a path that might do the trick. The addition of an extra person or persons really works for me. Might be worth a shot for you.

I always try to think of the most unlikely option. I love taking a crazy concept and than trying to make it believable. This makes the story seem fresh. When I get stuck, I force myself to keep going. Try just making yourself keep on writing for an hour even without knowing all the answers. This prevents overthinking it.

I will say I think you have a great idea and lots of options. Is this for a short story or a longer work? I think with short stories it is easier to just go with it and let it unfold or to try a less likely option. Short stories are less scary to try something new for me at least.

Ok, I'm going to try and 'talk' this out while I think of it.

First, organized crime--my first thought is mafia. The other day I read a fascinating post on reddit about how the mafia controls much of the truffle industry. It was a surprisingly fascinating read. So--mafia, truffle business, we're looking at two major conflicts. Economics and secrets. Standard stuff with a bit of flavor. Pardon the pun, I couldn't resist. There isn't much that's secret about truffles; the business collapsed in WW2 and never really recovered, which is why they are rare and expensive.

Now let me go a little deeper. Mafia isn't just about business, it's about honor, or so I hear. Why didn't he go back to the mafia after his parole? Either they wronged him or he wronged them somehow. Either way a violation of honor. More likely he wronged them; if he was just a low level member he wouldn't be enough of a threat to anyone to warrant a setup or a hit.

So what's his motivation? Maybe he got tired of the life; maybe someone close to him was killed. A cousin or a brother; maybe he botched a mission. Yeah. He botched a mission, his little brother was killed. He went to prison, spent a lot of time thinking and decided he was done with the life.

What do you need to start over? Money. What's the easiest way to get it? Ex-cons don't exactly have great employment opportunities. Money isn't that easy to steal in large quantities from the mob, but you know what is? Product. He bribes or otherwise takes the place of one of the truffle runners and simply walks away with them. They don't last very long so he would have to sell them fast. That's where he makes his mistake; he sells to the wrong buyer. Maybe they get suspicious; maybe he accidentally sells to a cop. Either way he makes his escape, but the boss is made aware of the theft.

So now we have motivation. The boss is mad that he stole from him and dealt bad business, harming his organization's reputation. That doesn't sit well with him so he sends out his goons. If you go the cop route you could even have a subplot of the undercover detective working to bust the mafia via their truffle business. Maybe he approaches the MC, who agrees to work against them for a second chance. Anyway.

It's a combination of using your personal knowledge and asking why a lot.

Hmmm. I would usually try to figure out what kind of problem I want the protagonist to have first (aside from staying alive and protecting his girlfriend).

If he's stolen something from the mob then there's a question of what to do with it now that they're onto him. If it's money or diamonds or whatever, he has to figure out if he should retrieve it from wherever he hid it. Does he think about returning it? Find a way to give it to the girlfriend or try to convince her to come with him and use the money to fund a trip overseas?

Or is the conflict with his former boss one that's strictly moral? He got tired of shaking people down or killing folks. A History of Violence takes this approach. The protag wants to leave his past behind, but finds that in order to protect his family he has to do the thing he wanted not to have to do ever again. Or else he and his family wind up dead. So, that's a different kind of problem.

Depending on my protagonist and the theme(s) of the novel, I would pick one approach over the other and then work out smaller choices from there. Identifying the protagonist's personal/internal conflict can help you figure out what to do with the external conflict.

Layla Nahar said:

Rather than some examples of what the MC or boss might have done, I'm hoping to hear *how* people come up with those possible solutions...

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Sounds like you're asking "Where do you get your ideas?"

Personally, I make them up. I suggest you do the same thing. You are the writer after all, so figure it out. Sit and stare at the page until it comes to you, or go outside and take a walk, or take a shower… Do something until the solution presents itself, or until you lose a significant portion of your sanity and no longer care about the story. That's how it's done. That's how it has always been done. That's how it always will be done. That's the job.

Put in the work.

Figure it out, write it down, move on.

Some harsh answers, but I sympathize with the question at hand. I think your difficulty is that this off-screen character doesn't have a personality because he's off-screen, but unfortunately he still needs one so that he can have motivation. I'm a firm believer that the present can never be separated from the past. Consider the relationship boss and MC had. Were they friends? Was it purely work? Knew each other for long? Intimate? Family? Why don't they know each other anymore--more than 'he left the syndicate'--and why does boss want to know about him again? Because he's missed him so much or because MC stole ten million? Your MC feels in danger, but how does the boss guy feel? How did their relationship end?

Honestly, I just go with whatever will create the most drama/heartbreak/angst to the MC and see what happens, considering along the way whether I want mostly physical or mental troubles to come. Car chases vs. long nights of drinking himself to sleep, etc. Basically, boss needs to be real, even if we never see him, because he's real in MC's brain. We never see MC's childhood either, but he still had one and it still affects him (just an example, maybe you do see it in your book, but you get what I mean).

I will often write to someone I know about how annoyed I am about X problem and it usually will work itself out somewhere along the way. Or I take a long walk with music. But that's basically the thought process. As the last person who listened to my angsting reduced it down to: What do you want to happen? Okay, make it happen. Possibly the most irritating advice I've received all year--because it's useful.

I too am writing about people involved in and affected by organized crime (high five!) and it's been a bit difficult, because, uh, I'm not in organized crime, never have been, don't know anyone who is, and am unsure of what sources are accurate. So I kind of go wild because, well, what does anyone else know either? But then I worry I'm going over the top, so I just make sure my characters are believable. If they feel real, readers will more readily accept over-the-top actions from them. Hopefully? I feel the pain.