Best Laid Plans and the Greatest Stories

Courtesy of S L, Unsplash

In October of 2021, I stepped in to run a one-night game (a one-shot) of Dungeons & Dragons for my weekly crew. The plan was simple: take my friends, give them ten levels-worth of power, and (with a guiding objective) tell them to be evil in an average fantasy town. That one-shot didn’t end for nearly five months, spinning into follow-ups and other story arcs before fully wrapping up in as heartwarming an epilogue as I could muster. I cannot overstate this enough: I planned for one night of absolutely unhinged tomfoolery. That was how it started. We ended up exploring the freedom of choice, the capacity for redemption, the limits of chaos, the spectrum of good and evil, and, I kid you not, the power of love and friendship. This is the story of the Ravenous Flame: what they had thrown at them, what they threw back at me, and what I learned from them.

Best Laid Plans

I’m a pretty meticulous planner in my life, especially when it comes to tabletop games. I have stat blocks, maps, playlists, everything set out exactly where I need it to be, ready to be pulled in at a moment’s notice. Yes, it’s a matter of preparation, but it’s almost more for my benefit than my players. I like to know how the field looks, I like to have the music going through my headset, I like to have my enemy information handy. My players are just lucky enough to benefit from my preparation. When I’m able to have that much prepared, I feel like I can bob and weave with whatever players throw at me more effectively.

Bits and pieces of my old writing has a chance to come out when I plan D&D; I love writing title crawls, and other quick setpiece information that I can share with the players, setting the vibe and painting the scene. I had some mechanics laid out to (hopefully) prevent the players from wiping the floor with their foes too quickly, tacked onto (or emphasized) from the standard D&D Fifth Edition ruleset. We were all set to game, I was prepared, and the inciting incident awaited.

The first arc could be summarized as: “you are evil, and your boss is evil. Your boss has instructed you to clear the way to the center of a town. No rules of engagement. Be evil.” At the end, I had a big bait & switch planned: evil characters are wont to be evil, so I would make them fight each other in a final battle royale. That was everything I had planned.

But, as any Game Master will share, there’s only so much you can plan for. Players will always find ways to keep you on your toes, and my blessed friends were no exception.

I couldn’t, in a hundred years, have planned for the characters they would have created: Gargax, a traditional (albeit, badass) conquest paladin; Bouldy, a rock-themed barbarian coming from my Hades-obsessed friend; Arkham, literally a Chaos Incarnate sorcerer; Fife and Jezrial, two Bards, albeit wildly different, when one is already plenty; and Blastwave, an artificer that (my friend’s words, not mine) was “basically Soundwave from Transformers.” With those as my cast, trying to maintain decorum as I played out their boss, the God of Destruction’s chosen one, was an exercise in restraint and adaptability. Softening this vessel of Evil for, if no one else, their closest lieutenants, led to some genuinely nice moments between them all. Aside from my characters, the dialogue, the dynamic between the player characters, was equal parts unpredictable and baffling. But still they carried on. They received their mission and were released to complete it.

I couldn’t have planned for their choices. Some standouts include: straight murdering a child, shooting a lady in the face after she demanded to be addressed as a lady, blowing up a windmill, eating a group of adventurers, and summoning a mosquito demon. Some choices required making new things up on the fly; the existence of a windmill to blow up, for example. Maybe another kid who was hanging out with his now extremely dead friend, so the more manipulative bards could flex their skills.

The choice that I absolutely had not considered, though? Subtlety. You plop a bunch of Level 10 player characters into the world and tell them, “Go apeshit,” you expect them to bum-rush the front gate and start wreaking havoc. Nope. Not these ne’er-do-wells. They decided to talk their way into the front gate. Mostly.

And therein lies the point that I still joke about to date as the wildest part of the adventure: a four-way party split in a six-character party. Am I disappointed my lovely chuckleheads couldn’t stick together for ten minutes? A little. Was it an excellent exercise for me in pacing and making sure the spotlight was shared evenly for everyone? Absolutely. Did it lead to a phenomenal cliffhanging device that I dub “the freezeframe”? Yes, yes, yes. Picture this, in four separate points across the city: Blastwave is shooting a woman in the face, Bouldy and Gargax are action-movie jumping away from an exploding windmill, Arkham just crawled out of a barrel to summon an abyssal mosquito, and Fife and Jezrial were just outed to a “good guy” adventuring party as bad guys.

And yet, their biggest surprise was yet to come: after a long bout of combat, of (like I mentioned) eating the aforementioned adventurers and scraping the ground with a different chosen one, their god, the God of Destruction, manifested in the world, killed their boss, and told them to kill each other for the right to be its next chosen one. At first, they started as planned. Arkham, the chaos sorcerer, actually died for a bit. And then, seemingly no sooner than they had started, they started to turn on their god. Impassioned speeches rising out, not from the bards, Jezrial or Fife, but from Blastwave. Pleas turned to anger, anger turned towards an untouchable being, culminating in the sentiment of “Hey, God? F*** you!” The encounter shifted; both previous chosen ones were transformed into puppets of fire, combat kicked off again, and Blastwave prayed to another god for help: the same god whose chosen one they had killed no more than ten in-game minutes ago. The same god who, rolls be damned, saw fit to give them an escape as the God of Destruction faded from the space, driven out seemingly by spite alone.

All of my planning, all of my preparation, and I remember not having a music track loaded for that turn of events. The one thing I could not expect in an evil adventure was the power of friendship winning out. We ended that session, and that first arc, in musical silence as we all came to grips with what just happened. There was no way we could just leave it on that nebulous note. No, of all the things I didn’t expect from these games, I didn’t expect to fall in love with these characters. I didn’t expect to need real closure on them, and a simple hand-wave of “you got away” wouldn’t suffice. I needed more. And, luckily, my friends were along for the ride. We had planned for a one-shot that already turned three session long. We were in it for a long haul now.

The best-laid plans of mice and men (and Game Masters) often go awry, but that’s not necessarily a bad thing.

One-Way Ticket, Open Seating

Many people (especially players) lament their games being railroaded, guided on a singular track, regardless of the choices they make in-game. Flagrant planner that I am, I don’t see as much wrong with it: stories need a structure, and there are far worse sins to commit in a game so dependent on narrative and motivation. That’s where those chaotic little gremlins/Player Characters come in: I can control the world, but I can’t control them. I envision my games like I envision the ideal train ride: one direction, but open seating. Plenty of people to interact with, new views and perspectives of nature to take in, variety and unpredictability, but, in the end, you’re still getting where you need to go.

The second arc involved the PCs, (mostly) reformed of their evil ways, raiding back into their old stronghold to rescue a prisoner: a seemingly-feebleminded woman who, in the past, served as a teleportation vector for their organization.

Every arc of the “one-shot” led with a briefing: players were given a main objective by some leadership they were allied with. Storm the village. Rescue the prisoner. Reach the mountaintop. Arguably, even the larger campaigns I write out have that same structure: stop the undead attacks. Find the giant machine. Get the keys. And so on. One guiding objective that they may approach from different angles, but the endgoal remains.

In the end, my players all get where I need them to go: all paths eventually converge because, again, I am at my best when I can use what I’ve planned. It’s to their benefit as much as it is mine. But on the way, as per open seating, I give them some liberties. Sometimes, it’s as simple as “I want to change my subclass, given how my character has evolved since the first arc.” Other times, it’s letting them build an airship in the span of time between arcs, and now having to factor in an airship to major encounters. Or maybe it’s befriending a would-be hostile dragon in a separate one-shot, designed to challenge them in combat, and having that dragon make a return in the final arc as an allied force. Again, the players still got where I wanted them to go, I just accommodated some other elements. Freedom of choice, balanced with a set path.

That freedom of choice goes the other way, too. The freedom my players had to do whatever when they were full-blown evil, the choices they made? Those didn’t go away. By the time they re-upped and weren’t associated with their bad guy boss anymore, other people still associated them as such. They were still known as the Ravenous Flame, lieutenants of the Avatar of Destruction. Allies were yet-distrustful of the PCs, given their history. An entire town was in shambles after what they had done. Family members of the eaten adventuring party were out for blood. Choices have consequences, and they were bound to catch up on a one-way trip.

More than anything, it continued to be the interactions of the player characters that colored the adventure most vividly. Sometimes, it was the traditional: bards making music, barbarians being rage-y, paladins being focused, and the like. Sometimes, unexpected: the artificer making impassioned speeches, or the deceptive bard having a moment of true reflection. Sometimes, completely out of left field: the chaotic sorcerer existing in a way that endangered his life, his party’s life, and his life at the hands of his party, or befriending a dragon specifically designed to kill them. Giving them the freedom to describe their old rooms in their old stronghold, how they left them before rebelling against their old master. The characters are the paint that fills in the outline of a world I’ve created. Sometimes they go outside the lines, but hey, if the Abstractionist movement can gain the traction it did, so can my funky D&D games.

Alright, last train metaphor: the last stop. If you’ve ever had a good train ride, you know that there can be something endearing about it. Getting off the train leaves you happy for reaching wherever you’ve gotten to, but just the same, it should leave you excited to return to that train. I always want my players excited to return, so I hit them both narratively and mechanically at the end. One final story beat that came out to a new character enlisting them to help her kill a god, their God, the bewilderment of the party, and curtains. Mechanically, I told them to bump up six levels, to level sixteen. In a game system where one level is usually a huge milestone, jumping six spelled out both excitement and dread in them. All according to plan.

Everyone got where I needed them to go, based on what I’d prepared and planned for them, but they still got to experience their own ride, their way.


In a time of video games that tout multi-hundred-hour experiences, or book series that seem to stretch toward the end of an author’s life, or cinematic universes that never fully end, I love endings. I love closure. I love being able to end a story, appreciate it, and then let it be. To that end, I’ve not played a tabletop campaign to completion, but have always wanted to. Again, the sense of closure, of finality in a story, even if the world keeps popping into new adventures…our adventure ends. We were barreling towards an ending with the Ravenous Flame, one I’d had planned out for weeks and months. I had to make the ending worth it, whatever form my players would morph it into.

The third arc began narratively where the second one ended: preparing to kill Maw, the God of Destruction, although some years later.

First, I wanted to give something at the end of the second arc: powerful items that would be useful in the final arc, something personalized for each of them. I’d been stingy with most non-potion items, and they deserved something nice after everything I’d put them through, and everything I had planned for them. Many were vehicles for 9th-Level spells, the highest level players could cast in the game, but some were just fitting for them. Otherwise, they still got loaded up with potions and, put simply, “Cleric Gloves,” because hardly any of them were capable of high-level magical healing. More than anything, this was my effort to try and balance what lay ahead.

Their goal lay at the top of a mountain, where they and the conflicts’ two armies were largely on ground-level. There was a cinematic approach to the mountain (“Just tell me what you do”) before transitioning into tracked combat. Enemies were mostly minion-levels of weak, some much stronger by comparison, but hardly a challenge for a high-level party. It was partly for fun, partly to soften them up before the mountaintop, partly to get a feel for how they fight at level 16. I gave later, harder enemies different abilities, but I wanted to ferret out how best to challenge my players. Day’s end, the journey up the mountain, and arguably the first battle on the mountaintop, was a steamroller: a fun rollick at a high level, just toying with enemies now so far beneath them.

Then it was my turn. We had our fun, now it was time to earn an ending worthy of the journey we’d gone on. Maw was operating at near-maximum stat capacity. Almost 1250 Hit Points worth of damage between all three different forms: a powerful, fire-based spellcaster; a massive, unhinged monstrosity; and an unpredictable, fluid crystal. Any attacks from it were guaranteed hits, and it hit like a divine truck multiple times in its turn, to say nothing of what it could do between its turns (light multiple people on fire, regenerate its health pool, breathe out a field of pure destructive energy, etc.). Each form played a little differently, from consciously strategic, to more stationary and powerful, to erratic and seemingly primal. It was beautiful, and it worked out perfectly with everything I’d given to the party. The scales tipped from their side, to Maw’s side, back and forth for a number of full-length sessions. Players would fall and be revived as Maw took massive abuse on my end. Plans would succeed on both our sides. Plans, similarly, would be foiled. But this was a culmination: the players, narratively, against an enemy that had dogged them since their first arc; me, mechanically, trying to challenge them and make it feel fair, given the resources available.

Our story, after so many sessions of fighting, finally reached its natural conclusion. Now, I’m no stranger to the popular “How do you want to do this?” trope in popular TTRPG livestreams, especially the likes of Critical Role: players who deliver the killing strike are given narrative control over the deathblow by the Game Master. I took it in a step that made sense to me, this enemy being a God, after all. The player who depleted Maw’s health essentially pinned the crystalloid to the ground, leaving it open for attack from their five allies. All of them got to have a shot at the God of Destruction, chipping away at it and making the deathblow as much a team effort as it could be. It was not a moment of How You Wanted to Do This, but a round of How Everyone Wants to Do This.

We reached the point I had been the most excited for: the end. The final blow was dealt, the threat faded, and I spoke some words to establish setting. What would a group of people, once so destructively-motivated, do in the moment after they destroyed their old Lord and Master?

You know what Arkham, our beautiful, chaotic, self-destructive sorcerer, did? His super-cool item was a wand, with seven charges. You could expend one charge in a turn and roll some shenanigans on a wild magic table only I had access to. You could expend more than one charge in a turn, but doing so would damage the user. You know what that mad lad did? Of course you do. He burnt all seven charges in a celebratory burst and went unconscious in a burst of chaos magic. All seven surges took effect: he turned into a potted Treant, began teleporting, started flying, shot over a thousand gems onto the ground, a Magic Missile and a mountaintop-spanning Fear spell both failed, and a spectral shield briefly appeared. Somewhere in there, he rolled a failed death save, and then a Natural 1, which immediately killed the sorcerer. An allied cleric ran up, ready to bring him back to life, and hesitated.

I looked at Arkham’s player, and asked them point blank if they wanted Arkham to come back to life. He pondered it for a moment before answering with a nonchalant, “Yeah, sure, what the hell.” So flippant! So cavalier! So I made him roll to convince me. Needless to say, he failed, and Arkham died how he lived: chaotically.

But what did everyone else do? Blastwave fell silent, comforting other non-player characters who were beside themselves with emotion. Jezrial ran off to go find their dragon companion, praying they were still safe elsewhere on the mountain (spoiler alert: they were, despite taking some hits). Fife composed another ballad, wordless and beautiful, on the peak of the scorched mountain. Bouldy gathered the fallen Arkham to ensure respects were (eventually) paid. Gargax worked their way down the mountain to survey the damage and help those who remained, both allied and (former) enemy. Those who started out as forms of Chaos, Violence, Conquest, Deception, Cruelty, and Obliteration ended as embodiments of Chaos (some things never change), Comfort, Redemption, Friendship, Beauty, and Remembrance.

I gave another quick block of text: it was a time of calm, of relief, of new understanding in the face of near-destruction. And I turned it back to the party: what do you do with your life now? Gargax started a new paladin order to help others redeem themselves, as he was redeemed. Jezrial, with their dragon friend, does their damndest to protect others and quash the thought of Maw’s return, while only occasionally dreaming of giving in to baser, warlord-adjacent tendencies. Fife travels, shares stories, inspires people, and makes music. Bouldy goes to defend others, traveling where others might need defending. Blastwave does some true-blooded artificer stuff, and starts advancing societal technology faster than I had planned for. Most campaigns end with that curtain call, a happily ever after. But I wanted closure, the closure I had been planning for months.

I gave more prose, and prompted them one more time: “You have shared how you live. Now, how do you die?” As always, they controlled their characters without any restrictions from me. Gargax led a paladin order of redemption, started a family, and died of natural causes. Jezrial perished on an adventure with her dragon friend, protecting them while they slept. Bouldy established a village, mentored others, and died peacefully while drinking tea with a neighbor. Fife traveled less and less, but keeps playing for anyone who visits, literally up to her last breath. Blastwave established a museum, lives a long life, and chooses to shut down in an exhibit dedicated to his friends and their lives.

The players controlled their characters, but I controlled the world. Gargax was offered (and accepted) ascension, the equivalent to sainthood, after his death, and now exists as a lesser deity. As Jezrial died, buried under rocks, they heard anguished screaming from a creature that had never known anguish before. Bouldy was welcomed into the Beyond by all of his ancestors who had gone before. Fife’s melody seemed to continue after she had stopped singing, somewhere Beyond. The thing Blastwave sees before fading are both people who want to help him and people who respect his wishes.

I finished off the arc, and the music finally stopped. Then, I implemented the consequences into my setting: Gargax got an entry in the Deities document, and may be encountered by future players. Jezrial’s dragon-friend is now wandering the world, able to transform into an imitation of Jezrial. Bouldy canonically founded a major northern city. Fife had an entire holiday and celebration kicked off because of her impact. And Blastwave’s museum still stands. Even Arkham, where he was buried off-screen, has spawned a grove of chaotic magic that other players may one day stumble upon. There was closure, and there was impact in everything that happened. In these small ways, I gave control of my world to my players, based on the actions they took, the characters they made, and how it all came to a close.

“Your story lives on.”

How it started was wanting to do something fun with my friends. Let’s be evil for a night or two, that should be entertaining. How it went was indescribable, despite my efforts. We made a story that I never could have predicted.

It was a story of evil triumphing over good…and then evil triumphing over evil…and then a lot of moral grey areas. A story about how my friends sent me in every wild direction they could, while I still tried to find ways for my meticulous planning not to go to waste. A story of both of us meeting in the middle for something unexpected, and wonderful, and beautiful. The thrill. The exploration. The potential. The story.

When people ask me why I love games so much, it’s because of this.



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Mike Shepard

Mike Shepard

Just an amateur reminding himself of what he loves. Looking to write about all the things and experiences that make the end of the world worth living in.