What Breaks You Open

I was in high school the first time a short story made me cry. I don’t remember which one it was, but I remember putting it down and sitting there for a while feeling like something had been broken in me, in a good way. Whatever superpower the writer had to wreck me in ten minutes I wanted to know how to do too.

I set writing aside during my twenties, but about fifteen years ago I finally began to figure out how to write in earnest. It’s only in the last few years I’ve been able to write stories that make me cry. And in the last year I’ve been building the thing I’ve wanted to build for over a decade: a literary world called Vesper, told through short stories, novellas, short film, and artwork. AI is part of how I build it. This piece is about what it took — fifteen years of learning craft, a year of collaborating with AI, and why one doesn’t work without the other.

The world is at thelastlamp.com. It’s free and open to everyone. Judge the work for yourself.

Why am I sobbing

I’ve been obsessed with stories and worlds since I was a kid. I played D&D back when it was dice and paper and very uncool. I read everything from Tolkien to Asimov to Arthur Miller to Tennessee Williams to whatever short story writers I could find. I watched both mainstream Hollywood blockbusters and also international and indie films and I was struck by how completely different the emotional impact was. I started asking myself why some movies or books just entertained me while others left me sobbing and changed on the inside.

I was particularly struck by how powerful short stories and plays were, despite their shorter length and stripped down plots. How they could be so much more devastating than a novel three times as long or a densely plotted Hollywood movie that cost millions of dollars. I remember thinking that I wanted to be able to do what this short story writer did to me. So for a while in high school I was sure I was going to be a writer when I grew up.

Instead I got pulled into activism and social entrepreneurship in college and ended up co-founding and running an anti-trafficking organization in Washington, D.C. through most of my twenties. I’m proud of the work but years of fourteen hour days left me utterly burned out, and at the end of it I had to ask myself what I actually wanted to do. Not just what would help others but what would actually make my soul happy. The answer surprised me. It was still writing.

So about fifteen years ago I started to seriously study writing craft. Robert McKee (for me, the master), Sol Stein, Raymond Obstfeld, Charles Baxter, and then later Matt Bird. I finally started to have the answers to the question my high school self asked – why did certain stories merely entertain and others absolutely wrecked me? Why did some movies leave me feeling depleted and numb, and others left me more connected to my heart, more awake to what really matters in life.

The simple answer turned out to be craft.

What I hadn’t understood before was that there is a tremendous amount of invisible structure and technique and discipline behind the stories and films I loved the most. I started to pore over my favorite books and plays and short stories and read them with completely new eyes, seeing all the craft that had been totally opaque to me before.

The ideas for stories and worlds started flowing out of me, and for the first time I had some tools to actually shape them. I practiced strictly separating the surface of the dialogue and action from the deeper subtext, the emotional charge underneath, making sure nothing was on the nose. I learned to make dialogue oblique, to keep characters from explaining what was actually going on inside them. I changed my prose style to be as plain as possible, cutting out purple writing and the self-conscious literary phrasings I’d been so proud of in my twenties. The discipline of restraint, of keeping subtext as subtext, of severely limiting how much the narrator explains so that you trust the reader to do the work. That’s what lets the emotional charge build and build under the surface until it can’t be held anymore and erupts. That discipline of restraint and the build toward eruption was the invisible structure behind almost every story I’d ever loved.

But understanding it intellectually and being able to pull it off are two very different things. It takes a lot of practice and nuance and good judgment, and it took me years of writing many painfully bad stories to slowly start getting any better.

And restraint and structure alone can’t carry a piece. For me a good story needs at least three other things alongside the craft, and one bonus thing which elevates it even more.

The first is dimensional characters who contain ironic contradictions inside themselves. Radu from a Vesper story called The Buddhist is an intellectual and a spiritual seeker — but if he were only that he’d be flat and uninteresting. He’s also built like a tank and roiling with suppressed rage that he’s spent his life learning to sit with. These contradictions usually reflect the specific traumas a character is carrying, and writing them in a way that feels earned rather than slapped on requires actually understanding how these patterns move through real people.

The second is symbolic objects, often ordinary ones, that get charged with meaning over the course of a story. They matter so much because they let the most emotional moments happen through action and image rather than through explanation, and explanation in those moments kills the scene dead. A clear example is the wooden boat in a Vesper story called The Boat. It’s a small toy boat carved by a father for his son, then given back, then found after the father’s death, then eventually passed along to another child. Each appearance layers more meaning onto the object, and that meaning would be totally lost if anyone tried to say it out loud.

The third is the specific life experience and worldview of the person writing the story. This is what gives any writer’s work its particular feeling, its sensibility, its texture, its depth. I’m forty-seven, half-Chinese, a husband and father of three. I grew up in the suburbs of Boston and I live in the old town of a city in Transylvania. I’m somehow both Buddhist and Orthodox Christian. I’m a former social entrepreneur, I still play D&D, I love nature, I used to collect insects as a kid and had a box with beetles pinned in it, I have serious childhood trauma I’m working through in therapy, and I’m a dork who writes stories that make me cry before I’ve even finished writing them. All of this stuff shows up in the stories and is what makes them feel like mine rather than generic. A story without this kind of specificity ends up soulless no matter how technically accomplished it is.

And last, the bonus thing, is to have the story be part of a larger world, so it’s not only telling the story of the characters, but also bringing to life a world around it. This is why I loved and still love D&D, Tolkien, and Game of Thrones. All of them helped me discover the pleasure of building a particular world through story, with its own unique aesthetic, value system, cast of characters, allegorical themes, and ongoing plots. For me it’s one of the things I most enjoy about storytelling.

This is awkward

Discovering craft unlocked my desire to write stories like nothing else in my life ever had. But there was one very awkward problem for my budding career as a writer.

I didn’t enjoy writing prose.

I loved crafting stories. I loved sitting with the architecture of a scene and the larger story and figuring out what stayed on the surface and what stayed buried, where the pressure built and where it broke. I had a good inner sense of characters and how their particular traumas drove them and the conflicts within them. I enjoyed feeling out the emotional arc of a story and landing it. And I especially loved doing all this in the context of world-building.

This was the part of writing that felt like what I was meant to be doing. But the sentence-by-sentence work of translating a clear scene in my head into language on a page was a different cognitive activity entirely, and I found it slow and frustrating and unsatisfying in a way I never quite managed to get past. As a world builder it was especially frustrating, because the pace of my output meant that the world building was happening at an agonizing crawl, leaving most of my ideas as just that, ideas in my head and not stories on the page.

I eventually got better as a prose writer, but still did not enjoy it very much. Which is an awkward problem if you want to be a writer, since, unless you are writing as part of a team, the prose writing aspect of a story is not negotiable.

For most of my thirties I kept writing anyway, slowly and without as much enthusiasm, and didn’t get very far. Then two things happened that changed everything.

First, I became a dad and I rediscovered storytelling as something I could do out loud. I told my kids stories every night. I ran huge D&D adventures with them, somewhere along the way traumatizing my four year old with a green hag for which I have not been fully forgiven. Some of the craft I’d learned over the years could now go into stories that never had to become prose, that lived in the air between me and my kids, and it helps me remember why I’d wanted to do this in the first place.

Second, AI started getting good at prose.

What AI does badly

When I first tried using AI to help me write stories it was just awful. AI is trained to write prose in a style that is the complete opposite of mine in almost every way.

Instead of suppressing subtext, it wrote everything on the nose. Characters announced their feelings and were happily vulnerable in a way that was both unrealistic and killed the build.

Instead of trusting the reader, it compulsively explained everything that had just happened, never letting the reader do any of the work themselves.

Instead of dimensional characters, it wrote generic and stereotyped and flat ones, people who you couldn’t love because they didn’t feel real.

Instead of creating a slow build toward eruption, the subtext didn’t just leak early, it sprayed out like from a hose at the first opportunity.

And instead of plain prose, it wrote purple prose with too many adjectives and adverbs and clever writerly phrasings that called attention to themselves. And don’t even get me started on the em-dashes.

This was what critics of AI accurately call slop. Because that’s what it was.

In fairness, AI is trained to write clearly and to explain patiently, and those are virtues in many kinds of writing, especially non-fiction writing. But they are exactly the wrong instincts for literary prose, which lives or dies on the discipline of restraint. The default AI output was completely unusable for what I was trying to make, and I almost stopped.

The workflow

What I figured out, slowly, was that AI could actually become useful for literary prose if I gave it two things.

The first is a highly detailed writing guide. Mine for Vesper is fifteen pages long, currently in its fifth version, and gets updated as I keep learning. I’ve included everything I’ve learned over the years about restraint and subtext, plain prose and oblique dialogue, use of symbolic objects, absence of narration or explanation, what to cut and what to keep. Some of it is direct rules. Some of it is example passages of the style I’m after. A lot of it is what not to do, with specific examples of slop I’ve watched the model produce so it knows what I mean.

Here’s an excerpt from the section on Separation of surface and subtext:

The second is a detailed creative brief I write before every story. The brief is usually as long as the finished story itself, and in some cases even longer.

In it I work out the general flow of the story. I write the characters, their traits, their mannerisms, their ironic contradictions, their backstories, the specific traumas they’re carrying and how those traumas show up in this scene or that one. I work out the inner and outer conflicts, the emotional architecture of how they play out across the story. I decide what stays on the surface in the dialogue and the action and what has to be kept unsaid in the subtext. I choose the symbolic objects, what they mean, where they appear, how they accumulate weight. I detail the settings, the world elements, the specific feeling each scene should evoke. Then I break the story down scene by scene, walking through each one, so the structure and the pacing and the build all work together to create the eruption when it comes. I write down what the story cannot do and where it cannot go.

Here is an excerpt from the Creative Brief I wrote for the Lamplighter’s Daughter. This part focuses on the main character of Zara:

Based on the Vesper writing guide and the story’s creative brief, I then have the AI generate a first draft, letting it write the prose to bring the story to life.

The first draft is never the final draft. Some scenes the AI gets almost perfect. More often I do rewrites scene by scene. Key moments such as the eruption scenes especially, and the final resolution scenes, almost always need to be done by hand because of the emotional nuance that is required. Every published story has been through multiple rounds of editing, with many sentences and paragraphs being rewritten by hand or being regenerated by the model in response to specific notes from me about what’s off. By the time a story actually reaches the site, the version on the page has been shaped sentence by sentence to be the version I want, and often restructured as well to correct larger issues that only became clear in the execution.

For The Date I wrote most of the direct prose by hand because the particular voice (stream of consciousness, fragmented, gripped by the pull of addiction) was too difficult for the AI. But that’s not a typical Vesper workflow. Most stories sit further along the spectrum, with the AI doing significant lifting on the sentence level and me doing significant lifting on every other level and a great deal of sentence work too.

That being said, I don’t think of AI as just a tool I’m using. A tool is a hammer or a piece of software like Photoshop. The AI is writing sentences that require decisions to be made along the way, at least at the micro level. And not everything is in the creative brief, so the AI also adds new elements to the story (sometimes for the worse, but often for the better). I think the relationship is closer to having a junior writing assistant who can produce fast, consistent prose, but who doesn’t have good instincts on writing style without careful instruction and doesn’t have the ability to craft a powerful story without everything being laid out clearly for it. My job is to provide all of that. The model’s job is to do the part of writing I never loved doing and was never fast enough to build the kinds of worlds I wanted to build.

Without the writing guide and the creative brief and the specific life I bring to all of it, the AI can’t write these stories. But without the AI, I also wouldn’t be writing them, or at least not at this pace, not at this volume, while also holding a full-time job and co-raising three kids. So I see it as a collaboration. That feels like the right word for it.

What the AI and the workflow can’t do

The first thing the AI is not able to do is to construct a larger allegorical world for the stories with a unified aesthetic and value system, a diverse geography of settings like the districts of Vesper, a cast of characters and creatures, and an overarching series of plot threads playing out in the background. This world building work is both too complex and too nuanced for it to do in a non-generic way, and requires a person to envision it and build it out bit by bit over time.

The second thing the AI can’t do is write prose in different styles. Or at least I haven’t figured out yet how to make this happen. The prose it can write with the writing guide is competent but a bit monotonous and this is an honest hit my work takes. When I wanted to write The Date in first person in the voice of someone in the grip of addiction, the AI couldn’t write the prose properly and I had to do it myself. I ended up enjoying the prose in that story more than the ones drafted by AI. So I acknowledge at some level I’m trading speed and pace of output (key for worldbuilding at scale) for the quality of the prose itself.

And last the AI struggles to write the most emotionally nuanced scenes, the subtext eruption and the resolution scenes, as it takes a different level of judgement and human emotional experience to land them.

Why I’m sharing all this

I think the version of AI-assisted writing that’s circulating in public conversation right now is mostly a caricature. Either AI is producing literary work entirely on its own from a prompt, which it isn’t, or AI is only outputting slop that any discerning reader would dismiss, which is mostly true but not all that is possible.

The Vesper workflow points to a middle ground where the creator brings the world, the story, the characters, the scenes and structure, and the deep craft understanding necessary to make a story powerful. And the AI does what it does best which is write solid (if not distinctive) prose as instructed by a detailed style guide.

The result is different work than I’d make alone. If I wrote all the prose myself it would be more distinctive and have a stronger voice. But for me, the AI is the difference between work that exists and work that stays in my head for the rest of my life.

I’m forty-seven. I have a full-time job and three children. I’ve been wanting to bring these stories out into the world for fifteen years. I want to do it at the scale that builds a world that feels like I can live it. I frankly don’t want to wait another 15 years to create a fraction of what the AI is helping me do now.

In high school, I thought I wanted to tell stories and build worlds when I grew up. I’ve ended up doing many other things since then. But being able to finally tell these stories, to bring these characters to life, to break myself open just like those stories broke me open all those years ago, has been the work that’s meant the most to me.

If you want a place to start in Vesper, The Boy is one of my favorites and what I recommend as the first story. The Lamplighter’s Daughter gives a beautiful sense of the world. The Date is one where the AI couldn’t write the prose needed and I had to write the prose myself. You can compare the difference. They’re all at thelastlamp.com. Free and open to everyone.