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Owned by Dillin

Master D&D Storytelling

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Build a D&D world so compelling your players would pay to live in it.

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Jesse Kroon

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2 contributions to Master D&D Storytelling
Here's the Secret to Keeping Players Hooked — Side Quests Included
Have you ever scoured a game like a hungry vulture, devouring every piece of content it had to offer? Red Dead Redemption was that game for me. I spent over 200 hours completing every story point, bounty, hunt, challenge, achievement, and side quest. I even set internal achievements that didn't offer any reward or progression — tossing people off cliffs, robbing outlaws, lassoing travellers and dragging them behind my horse, and holing up for a final stand in the local bar to see how high I could get my bounty. What about RDR hooked me to explore every inch of the map and tackle every side quest? Was it rewards like new horses, guns, and cosmetics? No. The rewards were marginal improvements at best. I might have changed my outfit twice my entire playthrough, better horses only seconds off travel, and gun upgrades only made kills slightly easier — nothing worth obsessing over. Was it that I wanted to impress my friends with a completionist trophy? No. That dragged me across the finish line after they killed my favorite character, but it's not what kept me in the marathon. What kept me engaged for 200+ hours were two things: characters I loved and compelling encounters. Players will push through the boring bits if it means spending time with a character they want to get to know more deeply. Take John Marston. He's a former outlaw trying to make amends and become a better man — relatable, flawed, and an underdog. He'll destroy anyone who threatens him or the people he loves, but he always offers his adversaries the courtesy of a warning before putting a bullet in their head. He's morally grey: Capable of being the hero or the outlaw in any situation, which keeps you guessing what he's going to do next. This is the kind of character that keeps you hooked in the long term. Compelling encounters give players the chance to shape their characters' stories through their actions. Early in the game, John Marston finds Nigel West Dickens, a snake oil salesman, shot and left for dead in the desert. John saves him, and the bandits who shot him give chase. After recovering, Nigel offers to help John track down his old gang, but first, he has John use his marksmanship to con an audience into buying snake oil to fund the search.
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What Does Impact Through Story Look Like?
This scene from Treasure Planet is one that I still remember after over 20 years. Jim Hawkins blames himself for failing to save the captain of the ship, Mr. Arrow from an untimely death. It was his job to secure the leylines to prevent crew from falling off the ship into space. Jim was finally beginning to feel he was a part of something beligger than his self, but after this devastating mistake, he doubts whether he deserves it. Dejected, he says, "For once, I thought I could do something right... just forget it." Silver responds in a way that surprises even himself. He encourages Jim in a way that only a father could. "No, you listen to me Jim Hawkins. You got the makings of greatness in you, but you got to take the helm and chart your own course. Stick to it, no matter the squalls! And when the time comes, you get the chance to really test the cut of your sails, and show what you're made of... well, I hope I'm there, catching some of the light coming off you that day". Just like Jim, I grew up without a father. And when Silver gave this encouragement, he spoke to my soul: "Believe in yourself and trust your heart. Even if you make mistakes along the way, it will lead you to where you are meant to be." For better or worse, stories are a powerful tool in that they are able to influence a person's worldview. Let's use this for good.
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Dillin Robbins
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@dillin-robbins-9372
Narrative Designer. Dungeon Master for The Crooked Moon D&D campaign at DigiPen Institute of Technology.

Active 4d ago
Joined Mar 12, 2026
ENFP
Seattle, WA