The finalists of last year's essay prize are published in The Best Internet Essays 2025

This is an "open" essay competition, meaning we want to impose as little restriction as possible on age, nationality, credentials, or affiliation. If you have reason to believe that local laws restrict you from entering, please write me an email (michael@michaeldean.site). Additionally:

Minors: Entrants must be at least 13 years of age as of the date of entry. For entrants between 13 and 18, submission constitutes a representation that your parent or legal guardian has reviewed and consented to these terms. If a minor wins the competition, their guardian will be required to sign a declaration of eligibility and a liability/publicity release on the minor's behalf.

International Entrants: Submissions from anywhere in the world are welcome, but if you are submitting from a country that is embargoed by US sanctions—Cuba, Iran, North Korea, Russia or the Crimea/Donetsk/Luhansk regions of Ukraine—then prize distribution could get complicated. Here are some options:

1. I can hold cash in an escrow until we get an OFAC license, which will likely be a very slow, if not impossible process,
2. I can honor your name as winner but assign the prize to a representative in a different country, following OFAC standards,
3. I can give you an equivalent non-cash prize (ie: Essay Architecture Credits).

Pseudonymity: Many publications and competitions don't allow pseudonyms, which excludes a growing number of online writers. Here, you're allowed to submit under your real name or a pseudonym. If you win, you can choose how to receive the prize and be credited:

• Private Payment: you can share your legal name and bank account or PayPal for prize distribution, while being publicly credited under your pseudonym.
• Charitable Donation: I can send the prize money to a charity of your choice (though I retain the right to veto).
• Public link: You can be publicly announced under whichever name you like, but winning the competition requires you to provide a link to a website or social media account that you own. This will let readers find you and read more of your work. This rule exists because if the winner is anonymous or has no online presence, it might be assumed that a prize was not awarded.

Single entity: You are not allowed to submit under multiple entities. Pick one name, real or pseudonymous. As you'll note below, multiple entries are allowed, but they all need to come from the same author. Multiple entities is the basis for disqualification.

All submissions happen within the Essay Architecture app, a paid service that gives analysis and feedback on your essay. Once in the app, you'll see a Submissions tab where you can enter your work to be considered.

Entry fee: Once your essay is uploaded into Essay Architecture and you've received analysis and feedback, there is no additional cost to submit to or win the Essay Architecture Prize.

Unlimited entries: You may submit as many distinct essays as you like (although only one can be a winner). You can also submit revised drafts of the same essay to see how your analysis improves (note: there is no editing after upload, and you'll have to pay for a 2nd upload). When submitting refined versions, please unsubmit the older one. Every single entry is judged independently on its own merrit.

Existing work: You are allowed to submit essays that are already published on your Substack, as long as they were written or published in this calendar year, 2025.

Formatting: When you upload, you will be able to use our Markdown editor to adjust headers, lists, and quotes (this is what our judges will see). Images and footnotes will not be factored in your score, but if the essay wins and is published, there may be an opportunity to include them.

Length: Submissions should be no less than 400 words and no more than 10,000 words. The length alone will not factor into the judging process. As a general note, the longer an essay is, the harder it is to structure, so do not feel pressured into thinking longer is better.

Topic: We are asking that you write a timeless essay about a particular moment in time, this year, 2025. Within that constraint, we have no prescribed themes you must follow.

Language: All essays will be judged in English. You may submit in another language, but it will be translated by AI. I recommend you translate prior to submission to ensure your intent is conveyed.

Deadline: The "Submission Portal" will close on Sunday, November 23rd, 2025 at the end of the day (realistically, early the next morning). I strongly encourage you not to wait until the last minute, not only to spare yourself the stress, but to avoid any technical difficulties. Late submissions will not be considered for the competition. We recommend submitting early to avoid last-minute technical issues. (UPDATED: 11/23/2025)

Backup Portal: In the event that the website crashes and you're unable to access the Submission Portal, you can upload a Google Document through this form.

Your Original Work: All submissions must be your original work. You must be the sole author. Submitting plagiarized work or work to which you do not have the rights to will result in disqualification.

AI Assistance: We believe AI can be a powerful creative partner. This competition itself is an example of AI empowering human writers. You are welcome to use AI for various parts of the process, including but not limited to ideation, brainstorming, drafting, and editing. However, with each submission, you'll be required to fill out a short survey to disclose AI usage. This will not be penalized, nor will judges have access to it; it is simply for transparency and research, to understand how writers are using this technology in their workflows. Innovative uses of AI may be featured in our post-competition writeup. If we have reason to believe you are being dishonest about your AI usage, or if your use of AI has resulted in plagiarism, you may be disqualified from winning.

Our evaluation is a hybrid process designed to balance objective AI-based analysis with subjective human insight. The final score is weighted equally across three different phases, creating checks and balances that consider craft, culture, and taste.

Phases:

Phase 1: AI Composition Analysis (33%): Our AI system analyzes each submission along the Essay Architecture framework, which includes thousands of evaluations across 27 patterns. Information about each pattern can be found on the website. This provides an objective composition-based evaluation framework that applies to all entrants.

Phase 2: Human Review (33%): Human readers (myself, and a small panel) will read through submissions to evaluate for non-compositional qualities (cultural potency, timeless appeal, singular aura, etc.). To ensure fairness, if a judge recognizes an author, the power of their score will be down-weighted relative to the other judges.

Phase 3: Guest Judge Ranking (33%): A shortlist of the highest-ranking essays is sent to our Guest Judge, who will then read and rank the set based on their own expert taste and judgment. The goal is to have a different guest judge each year, which will introduce an element of chaos and unpredictability, since each judge brings their own idiosyncratic sense of taste. The judge will not be required to reveal their criteria, though they will be invited to provide a write-up that is shared at the competition's conclusion.

Blind judging: Judges will not see your name or scores before reading and assessing your essay, and they will be presented in a random order.

No anonymity requirement: Some competitions ask you to exclude any identifying details and to scrub any mention of your name. This makes it hard to write a personal essay! I believe our three phases above are robust enough to prevent relationships with me or any of the judges to affect the winner.

Dynamic process: Our scoring methodology is experimental. This is our first time ever running it. If we adapt on the fly, we will be transparent about it. Through iterating, we hope to come up with a robust, fair, and effective system to celebrate great essays.

Final Verdict: The decisions of the judges are final and not subject to appeal.

Grand Prize: One Grand Prize winner will receive $10,000 USD. The prize will be awarded as a single lump-sum payment. We can pay via bank transfer, check, PayPal, or another reasonable method as agreed with the winner.

Finalist: In addition to the Grand Prize winner, several other essays will be featured as "finalists." They will receive public recognition, and their work may be published in various places, on our Substack, website, or in digital/physical anthologies. Note: in the scenario that someone has multiple essays that rank as finalists, it's likely that only one will be selected.

Notification: All potential winners will be notified by email and will have seven (7) days to respond and provide any required information. If we receive no response, we reserve the right to award the prize to the next-highest-ranking finalist.

Taxes: The winner is solely responsible for any and all taxes on the prize money. U.S. winners will be issued a 1099 form and international winners are responsible for reporting to their own tax authorities.

Publicity: By accepting the prize, the winner grants us permission to use their name (or pseudonym) for promotional purposes, as well as featuring portions of their essay, the entirety of their essay, and commentary on their essay.

Editing: In the event of digital or physical publication, we may provide minor copy edits in case we notice any typos or grammatical errors. The content or arrangement will not be changed.

You Retain Your Copyright: You, the author, retain full ownership and copyright of your work at all times. You are allowed to publish essays already on your website. If it's not yet published, you're free to self-publish during or after the competition as well. Regardless of how you use the Essay Architecture tool, please do not submit anything through the Submissions Portal that you are not the author of!

Grant of Non-Exclusive Rights: By submitting an entry, you grant us a non-exclusive license to your work. In plainer terms: we'd like to showcase your work if it wins, and you are free to publish it elsewhere at the same time or later. We would have worldwide, perpetual, royalty-free license to your work, which gives us the ability to feature your work, in the future, digitally or physically, while of course crediting you as the author.

Existing Contracts: If another entity already has exclusive rights over your essay (ie: a magazine, a publication, a contest, etc.), then please don't submit because technically you don't own it (but also congrats on getting published somewhere).

Removal: If at any point you wish to remove your winning work from our site in the future (for whatever reason), contact us – our license allows us to feature it indefinitely, but we're reasonable and will honor takedown requests if possible, once the contest cycle is over. Basically, we're not here to trap your creation, just to celebrate it. If your essay is already in print, there's nothing we can do.

Non-Winning Entries: We claim no rights whatsoever to non-winning entries and will not publish or use them without your explicit, separate permission.

Personal Data: Your personal information (name, email) will be used solely for contest administration and will not be shared, except as necessary to award prizes or as required by law. It will never be sold to advertisers or third parties.

API Usage: By entering, you consent for your essay to be analyzed by our system, which utilizes third-party APIs (e.g., OpenAI). According to their terms, any information sent through their API is secure and not used for training. If you do not want your text analyzed by AI, then unfortunately you shouldn't enter this particular contest, because that's core to our unique format. We're pretty transparent about this upfront. On the flip side, if you do enter, you might get some valuable insights about your writing (something most writing contests don't offer).

Internal usage: Your submissions will not be used internally to train or fine-tune a generative AI model. In order to improve my evaluation system, I will occasionally manually score submissions (on one or all patterns), and compare them to your AI-generated scores. This helps me know if the feedback your getting is accurate and valuable. By reviewing the differences between my scores and the AI-scores, I'm able to improve the system, without embedding your data into a proprietary LLM.

Score Privacy: Your individual scores are confidential and will not be released publicly along with your name, unless you are a winner. We may publish aggregated anonymous data on submission trends and composition scores, but you will not be identified.

Sensitive information: Your draft, analyses, and scores are stored in a database. Security measures are in place, but in case of the unlikely event of a data breach, please don't upload anything with sensitive information that you wouldn't include in a public essay on your website.

Malfunctions: The contest sponsors, administrators, and judges are not liable for technical malfunctions or events beyond our reasonable control. This includes but isn't limited to: network failures, server outages, website crashes, bugs, delays in transmissions, data corruption, unauthorized hacking or tampering, power outages, apocalypses (robot-induced or otherwise), or your email provider sending our communications to the void of spam. We'll do our best to keep things running smoothly, but if something goes wrong, we'll address it pragmatically (extend deadlines, fix bugs, etc.). However, entrants assume the risk of technical issues. We cannot be responsible for entries not received, or that are lost/damaged, due to these electronic hiccups.

App outage: In the event that the app crashes during usage spikes, you might temporarily lose access to the evaluation tool (both the ability to upload, and/or, the ability to see past results). This could last for hours or days. In the event that this happens near the submission deadline, you'll be emailed a "backup submission" portal where you can share your draft. Of course, we don't want this to happen, but just know that it's possible that unforeseen technical events might limit your access to the tool (so don't procrastinate and submit early!)

Not primary storage: Always keep a copy of your submission; don't use Essay Architecture as the sole home of your essay drafts.

Missing scores: If one of your patterns scores a 0, please let us know through our support email. This is an error (the lowest score is 1 … everyone deserves a point for trying). We'll fix it on the backend, rerun that pattern, and let you know.

Refunds: We don't offer refunds based on the feedback, but if you experience a rare and obstructive technical glitch, we will reimburse you with a free credit to upload again.

Agreement: By submitting an entry, you agree to abide by these Terms and Conditions and the decisions of the judges and sponsor. If there's anything you're unsure about, feel free to reach out to us with questions before entering. I'm here to listen and accommodate. These rules form a binding agreement between you and the contest organizers. The contest is governed by applicable laws of New York State, but any disputes should be attempted to be resolved informally. Any legal action or proceeding arising under these Terms will be brought exclusively in the federal or state courts located in New York County, New York, and the parties irrevocably consent to the personal jurisdiction and venue therein.

Changes: I reserve the right to update these Terms and Conditions at any time. Any changes will be posted on this page with a clear notice of the effective date.

No-Waiver clause: No waiver of any term herein by us constitutes a further or continuing waiver of that term or any other term. If any part of these Terms is found invalid or unenforceable by a court, the remainder stays in effect.

Right to Cancel: We reserve the right to modify or cancel the competition at any time for any reason (technical, legal, cultural, or otherwise, etc.). Considering that competition entry is a free bonus on top of the paid feedback you receive, there will be no refunds in the event of cancellation.

Your opinions are your own: We also don't endorse or assume liability for the content of entries themselves: the views and opinions in your essays are yours alone, not ours. If you libel someone in your essay, that's on you (please, let's not have defamation lawsuits).

Release and Limitation of Liability: By entering the Competition, you agree to release, discharge, and hold harmless the Competition organizers, their affiliates, partners, sponsors, judges, and employees (the "Released Parties") from any and all claims, liabilities, losses, damages, or injuries of any kind arising out of or in connection with your participation in this Competition. This includes, but is not limited to, claims based on: (a) technical failures of any kind, such as lost, interrupted, or unavailable network connections, or failed, incomplete, or delayed computer transmissions; (b) data loss, corruption, or other unauthorized access to or alteration of your entry; or (c) any injury or damage to person or property which may be caused, directly or indirectly, in whole or in part, from your participation in the Competition. You acknowledge and agree that the liability of the Released Parties is limited. In no event shall the Released Parties be liable for any punitive, indirect, incidental, special, or consequential damages arising out of the Competition. Your sole and exclusive remedy for any claim arising from the Competition shall be limited to the entry fee(s) you paid to enter. This limitation shall not apply to liability for death or personal injury caused by the gross negligence or willful misconduct of the Released Parties.