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15+ Winning Story Prompts

Good things do happen. But why save wins for the end? Turn your novel upside down with story prompts on winning and see where good luck takes you.

Good things do happen. In most stories, writers wallop heroes with tragedy, mistakes, breakdowns, or embarrassments before (hopefully) rounding the corner toward happily ever after. But why save wins for the end? Turn your novel upside down with story prompts on winning and see where good luck takes you.

Celebratory words, winning

The MegaMillions Lottery reached over $1.3 BILLION this January, and on Friday the 13th, one lucky person won it.

Leading up to the drawing, people flocked to convenience stores for tickets. Conversations around dinner tables were of the what-would-you-do-with-that-kind-of-money variety.

“My own writer’s retreat with an ocean view, cushy chairs, a robot-like assistant and an endless supply of sticky notes, fun stationery, and good pens… ah!” ~ Me, on what I’d do with the money, for starters. 

Everyone was talking about it. People were excited and ever hopeful. Good things do happen. Why not to me?

Good things can even happen to your characters. It can’t be all murder, mayhem, bad dates, and awful bosses, right?

Overloading characters with troubles is the usual kickstart to a story, but what if a win is an inciting incident? And a stroke of good luck causes your hero’s conflict?

Remember this old movie–It Could Happen to You–starring Nicholas Cage and Bridget Fonda? In it, Cage’s character doesn’t have enough money to leave his waitress, Bridget Fonda, a tip, so he promises her half the winnings of a lottery ticket instead–a situation that actually happened in real life in New York. Cage wins $4 million and keeps his word, splitting the prize with the waitress, no matter the trouble it causes. Yeah, his wife was pissed.

Anyway, the point is, good things do happen – even to down-on-her-luck waitresses who didn’t even buy a ticket. It’s a cool story premise for the main character to think… all my problems are solved! And then, reality hits, and the blessing becomes a curse.

Winning the lottery isn’t so far-fetched–it happens all the time. And so many story prompts can emerge from that idea…

  • The main character makes the mistake of telling a crowded bar that he has the winning ticket, and it’s a suspenseful race to cash it in before someone steals it from him.
  • A dedicated teacher wins enough to retire to an island, but she can’t leave her students or quit the job she loves. But when her win becomes public, everyone wants a piece of it. Her relationships change. People are jealous. Will she crumble under pressure and retire or do something drastic?
  • Buying the ticket was a whim, but Mia was down to her last dollar and at her wit’s end. Trapped in an abusive, controlling marriage, she’d tried everything to escape. Her latest attempt left her stranded at a gas station, dreading his reaction when she finally broke down and called him to pick her up. She held the ticket in her shaking hands–her last chance. If only she could disappear…
  • When retirees Ed and Mary win the lottery, they decide they’ll finally get to do what they’ve always wanted–travel the world. But when pirates overrun their ritzy European cruise, they wish they’d never won the money.

A BIG win can take many forms, though. Here are 10+ “Winning” Story Prompts other than the lottery:

Winning the HGTV Dream Home–I get obsessed with this every year. …Only it’s in another state, somewhere your main character has always dreamed of living. Is it fate? Only everyone wants him to take the cash, including his wife. Does he cash in or uproot?

An unexpected inheritance. A plotting favorite of Agatha Christie and perhaps many stories of that time, people’s wills have inspired many murders. But it doesn’t have to be the inheritance of an estate, title, or millions of dollars. What about inheriting a library? A strange collection? A family secret? A priceless antique?

Getting away with a crime could be considered winning… a high-tech hacking robbery, a revenge plot, a gambling con. What if your main character is a successful villain, winning at crime until…

A new car–the Griswolds won four in Vegas Vacation. To most people, owning a car isn’t a big deal. I’ve had one since I was seventeen. Living in a rural area growing up, a car was necessary to work or do anything since no buses or cabs would come out that far. What freedom might winning a car represent for your main character? And what might the win pull him away from?

A political office. Winning an election means a new job and that’s always bound to cause conflict, even if it’s what the main character wants. And the win doesn’t have to be obvious like Mayor or Governor. There are many smaller roles your MC could win. Start here for an office suitable for your hero in your story’s setting.

A game show–Check out the episode of The IT Crowd where Morris Moss wins a game show. Hysterical. He did it just for street cred. But the winnings could be anything. The Griswolds won the trip of a lifetime in European Vacation. What about winning a lifetime supply of ______ (the second-place prize), and then there’s a worldwide shortage of it?

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A spot on a reality show–there are soooo many of these now… take your pick! From dating to dancing to survival to cooking, there’s a reason the entertainment industry keeps coming up with new ones–we love watching people win (and fail miserably). What’s your main character so good at he could be featured in a reality show?

A sporting event. For this, I think of Bruce Willis in Pulp Fiction, promising to take the fall in a fight but winning anyway. That’s a win with consequences. But there’re marathons, ax-throwing competitions, bike races, and equestrian sports–just to name a few. How might an athlete’s win inspire dire outcomes?

A spelling bee, debate, cheerleading competition, scholarship, singing competition, dinner with a celebrity, date via charity auction, hobby-related event. Any of these wins could be the inciting incident springing your character to action… or despair if it’s not all she imagined.

A local prize from the radio station... free plastic surgery, braces, backstage passes, a chance to be a deejay, or meet the town’s most famous person. Could someone’s 15 minutes in the limelight bring about her undoing? Could it propel them into a new, better life?

An agent and lucrative book deal. Can the introverted, homebody writer handle the pressure of sudden fame, money, and public appearances? Or the pressure to pen more best sellers amidst the chaos? Ah, problems for future-me… I hope.

So, what might your main character win? Share your ideas below, and see if you win the prize for the best one! I’m kidding–there’s no prize except street cred.

For more story prompts like this, check out my blog. Get a cup of coffee or tea and spend some time with me.

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