What's it like to live in 2025?

In this post I cover the prompt for The Essay Architecture Prize, why I picked it, some approaches, our judging criteria, the rules, 50+ examples ... and the book is live!

Some quick announcements

• Two week ago, I announced I’m giving $10,000 to the best essay of 2025. The competition starts today! Below you’ll find the prompt and some details to help you get started. I’m putting some final touches on the software & submission tool, so expect that to come out by the end of this week. In the meantime, you can start brainstorming and drafting your ideas.

• The Essay Architecture textbook is live on Substack! This has been two years in the making. Paid subscribers now have 40 posts that cover every element and pattern of the system in detail. Free subscribers have access to A Pattern Language (an introductory essay) and the dimension pages, which give an overview and all the definitions.

• Check out my episode on Infinite Loops with Jim O’Shaughnessy for a conversation on Essay Architecture, this competition, writing, technology, and education. Big thanks to Jim, for the O’Shaughnessy Fellowship made this all possible (you should apply in 2026).

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The prompt:

What’s it like to live in 2025? Write an essay about a specific moment you experienced in 2025—an event, trend, media, technology, or relationship—that exemplifies both our current zeitgeist and our timeless nature.

I figured since you’ll be spending hours writing your own essay(s), I’d spend some time articulating the prompt, why I picked it, how to approach it, what we’re judging on, and a summary of the rules. There are also 50+ examples in the footnotes that might help you generate ideas. If anything isn’t clear, please leave a comment! (I’ll add a “clarifications” section at the bottom.)

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Why is this the prompt?

For an essay contest to be “open,” the prompt needs to be flexible enough for any writer to enter. Something obvious we all share is this specific moment in time. 2025 can unify a big range of very different essays. Our goal here is to publish 10+ finalists into an anthology; not only will it be a collection of solid essays, but also an artifact to make sense of the spirit of our times. Sense-making is hard in 2025: the open Internet is chaotic and polarized, and institutions have fixed ideologies. The hope is to curate a collection of independent thinkers who use personal experience to make sense of our society.

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How should you approach the prompt?

Approach “2025” in an angle that is most exciting for you (a prompt is really just a launch point that you should quickly abandon once you find inspiration). You do not need to tap into pop culture icons, or polarizing political ideas, or what you think everyone else collectively thinks this year is all about. Go deeper than hype and headlines. What feels significant to you this year, and what might that reveal about our culture? It’s okay if it’s extremely subtle and unexpected. Don’t feel the need to make it explicit (“I think the most defining moment of 2025 is X because…”). The prompt should be invisible. You need not even mention “2025” once. I also don’t recommend trying to summarize the entire year, month-by-month. Pick one moment and go deep.

I’ll share two general ways to approach the prompt (and really, essays in general). An essay is a personal reflection that links individual experience to socially relevant ideas. You might begin with the particulars of your own life, or, the broader patterns of culture, but eventually you have to bridge the two. An essayist fuses many genres—the pen of a poet, the imagination of novelist, the persuasion of a marketer, the research of a journalist, etc.—but most fundamentally, it fuses the soul of a memoirist with the insight of a philosopher. It’s about using your own life as a portal to understand bigger ideas.

1. Start with experience: What are some notable things that happened to you this year? These could range from obviously important life events to peculiar moments you can’t stop thinking about. What can you write about that almost no one else can? By starting here, you’re guaranteed to write something singular; the task then is to figure out how your experience is emblematic of a larger phenomena. Is it totally okay if your topic is not self-evidently symbolic of 2025. By getting into the specifics, you might reveal an unnamed current that we’re all entangled in. (Examples in footnote.¹)

2. Start with culture: What are some phenomena in the larger culture that you have a unique relationship to? Whether you cover a massively mainstream moment,² or a little-known event in an Internet subculture,³ it’s all about finding an idiosyncratic angle. It’s less about picking “the best” or most representative moment; it’s about finding one where your singular experience gives us the best lens to understand it. Whether you’re writing about politics,⁴ media,⁵ technology,⁶ language,⁷ or another domain, make it yours.

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What are we judging on?

There are three ways your essays will be evaluated: (1) the Essay Architecture framework will judge how well-rounded your composition is, scoring your submission 1-5 across 27 objective patterns; (2) the best-crafted essays will be read by a panel of human readers who look at 8 subjective criteria (listed below), because the quality of a work is more than the quality of its craftsmanship; and (3) a guest judge will serve as a wildcard, ranking essays based on their own taste.

Objective criteria:

To get a basic understanding of the Essay Architecture framework, you can check out my latest posts on Idea, Form, and Voice. In each you’ll find a short essay on the dimension, along with a one-line question that defines each element and pattern. It’s around 2,700 words total (which is far more descriptive than most essay prizes).

Subjective criteria:

Now, here are some subjective qualities of a great essay. (I’m sure these will evolve with time.) A great essay is not just well-composed, it’s singular, emblematic, timeless, catalytic, essayistic, emotional, experimental, strange, etc. These are less definable through patterns on the page; they’re felt by the reader, and colored by their experiences.

1. Does the essay seem to come from a singular life circumstance?

2. Does an insight reveal something surprising about 2025?

3. Has it connected a timely moment to timeless themes?

4. Is the core insight likely to provoke change in thought or action?

5. Did it capture the essayistic spirit: a mind working through friction?

6. Does it pack powerful emotions?

7. Does it push the boundaries of prose and experiment with craft?

8. Does it make the familiar strange?

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General rules:

(Detailed and boring terms coming soon)

• Open eligibility. Open to anyone 18 years or older (ages 13-17 require parental consent); open to most locations (unfortunately certain countries with US embargoes might have complications); pseudonyms welcome.

• $10k grand prize and 10+ finalists get published. There is a single cash prize, but the finalists will be featured in an anthology with a royalty split.

• Upload for $2-9 to get feedback and scores, then submit for free. Unlike traditional contests that charge a ~$24 submission fee and don’t offer feedback, the Essay Architecture software gives you a detailed analysis of anything you upload.

• Unlimited submissions. You can upload as many drafts as you want to improve it through feedback, but I recommend submitting one version per idea. But feel free to submit as many different ideas as you’d like for consideration.

• Written or published in 2025. Along with new, unpublished essays, you can submit anything you’ve written or published in 2025. Feel free to submit any of your existing Substack essays that relate to the prompt (you can edit them or submit as is).

• Flexible word count: Open to both short and long essays. The max word count is 10,000 words, but focus on quality, not length. It’s better you submit a 1,000 word essay that is dense with meaning than a 5,000 word essay that is ambitious in scope but poorly crafted. If you exceed 2,500 words, make sure the form/structure is tight.

• Blind judging: Your submission will be given a random ID number so that readers won’t be able to easily identify you. But since these essays will have personal elements, there’s a chance they might. If they think they do, they will guess who the writer is, and if they’re right, their evaluation will be down-weighted or omitted (you will not be penalized; the scores of blind judges will just have more weight than non-blind judges).

• English language: All essays are scored and judged in English. If you are writing in another language, please translate before you submit.

• AI policy: Some competitions ban all forms of AI usage. Given that Essay Architecture is an AI-powered editor, I’m more open to it. That said, the spirit of this whole project is to preserve the act of essay writing (meaning, in my opinion, you should use AI to augment your thinking, not to automate your sentences). But however you use AI, it’s welcome, as long as you disclose it. For each submission, there’s a little one-view survey that asks you to share how influential AI was in various parts of your process. Usage will not be penalized! This information will help me see aggregate stats and shape a more specific AI policy in the future.

• Data privacy: Essay Architecture uses OpenAI’s API. Data you submit through this API is not used to train their models (unlike the conversations within their product, ChatGPT). Additionally, I do not sell data or use uploads to train my own generative models. A good rule of thumb is to not upload any sensitive data you wouldn’t want on your personal website (after all, this is a tool for essays that you will be sharing in public).

• Submissions close on Sunday, November 9th, 2025 at 5:00 pm ET: Submit early to avoid any last-minute technical issues! In case everybody procrastinates and there’s a final-hour surge that melts the server, I will provide a backup submission portal through Google Forms.

Feel free to ask questions through comments or DMs.

Examples

1. Here’s an example of starting with experience: maybe you’re pregnant in 2025: you could write about 4D ultrasounds, asking ChatGPT on what you can’t eat, and your app that compares your fetus to fruit sizes. You don’t need to cover every detail of the pregnancy, but by focusing on the gadgets available to pregnant women this year, you can explore a timeless idea on how technology that’s supposed to comfort us can actually heighten anxiety. Anything you’ve experienced this year can be a portal to explore a larger theme: an essay about your NYC home search might represent the housing pickle of the millennial generation; an essay about attending the wedding of a writer you never met before in person speaks to the positive potential of the Internet; an essay about shopping for a mattress at your local SEARS might be a gateway to explore the slow death of in-person retail; an essay about a friend joining a mushroom church might be a symbol of the mainstreaming of psychedelics; an essay about your first ride in a self-driving Waymo in San Francisco might foreshadow our future of automation.

2. If you write about massive mainstream moments—the Jersey Drone phenomena, the Coldplay kiss cam incident, sending Katy Perry into space, the death of Brian Wilson—make sure you write the essay only you can write: Did you find a drone in the woods last winter? Were you ever on a jumbotron yourself? Do you have a young daughter who is suddenly obsessed with going to space? Did you go to high school with a Beach Boy? Remember, these are essays, not articles. It is not enough to cover something because it’s shocking or spectacular; we want to see the lived human experiences that orbit iconic moments.

3. Subcultures are a way to identify currents that are either about to become mainstream, or currents that are rejected by the mainstream. You could even write about a once rejected subculture becoming mainstream, like how Deadheads are surging in 2025. The Internet is filled with niche communities and odd memes; they often disappear quickly, but they can be symbolic of larger forces. Some that come to mind: a viral video of a fake five foot dog that got a quarter of a billion views, a video of a kid who brought his laptop onto the stage of his college graduation to open ChatGPT and flex to the cameras, a TikTok video of a girl who claimed to have been contacted by a Sumerian demon via a Ouija board to tell her that the world was ending on May 25th, etc. How do these online moments relate to your real life? For example I happened to be at the Bronx Zoo when the "Gorilla vs. 100 men” meme went viral, and it led to some very specific observations on gorillas.

4. If you write about politics—a Trump executive order, tariffs, Charlie Kirk’s assassination, how Gaza protestors boycotted Radiohead, the Diddy trial, etc.—try to be as non-partisan as you can. An essay is not the place to pick a side and take jabs from behind your screen, it is a space for the non-dogmatic exploration of ideas. It would be simpler to say “no politics” to avoid any controversy, but I think there’s a need to cover thorny issues in a personal and nuanced way.

5. Is there a specific piece of media you consumed this year that had an effect on you? Consider music, movies, shows, video games, commercials, ads, books, essays, content, etc. You could write about the Velvet Sundown album, Elizabeth Gilbert’s new memoir, the Sydney Sweeney commercials for American Eagle, Severance season 2, Anora, Sam Altman’s essay “The Gentle Singularity,” or how Google Veo 3 reels resemble interdimensional cable from Rick and Morty. This isn’t about writing a “review,” it’s about using an object as a portal to launch into your own experiences, insights, and ideas. For example, you might use Mission Impossible: The Final Reckoning and it’s AI villain as a frame to explore how movies doesn’t build accurate models of technological risk (and Mission Impossible might only be 10-30% of the essay). It doesn’t matter how well-known the work is. What matters is that you pick something emblematic, give us the necessary context, and make it yours.

6. You could focus on technology (products, trends, infrastructure, laws) that came out this year: chatbot psychosis, data center construction, the launch of GPT-5, home robots that claim to do laundry, social media age laws, mosquito-sized surveillance drones, data from the James Webb Space Telescope, Claude’s “spiritual bliss attractor state,” vibe coding in Cursor, $TRUMP coin, Meta’s talent poaching, Google’s removal of their “no AI weapons” clause, etc. Whatever you pick, how does this technology relate to you? Are you a user? A builder? Do you know someone with a weird dependency? Did a high-tech experience surface something from your childhood?

7. You could focus on language, like new words added to the dictionary this year (includes: tradwife, delulu, broligarchy, slop, decel, etc.), old words that have gained new meaning (agency), or trendy slogans (“you can just do things” or “cheat on everything”). You could focus on new cliches and aesthetics, like the overuse of em-dashes in LLMs, or the presence of the grotesque in AI image generation. What might a single word imply about an entire year?