Status: just a braindump, though feel free to comment (if you can figure out how Notion comments work!)
For background context, see https://manifund.org/essay
Thoughts while grading April 25, 2026
- Wish I’d pushed more for deep dives; specific rather than overviews
- maybe because I scored so many similar essays, I placed a higher value on novelty, and lower value on anything too generic or surface-level of an explainer
- (maybe this is how college admission essay readers feel)
- (not exactly the best grading criteria)
- Many of my favorites were of the form “someone blogs about their personal experiences”
- Seems like many submissions ended up being very “guess the teacher’s password” — eg lots of writing about prizes
- Kind of wish someone had perfectly guessed my password, like I have the one question and somebody writes the essay I would have written if I had the time to write it
- Some submissions suffered from pie-in-the-sky or “this would be good for someone to do” or “if I was dictator of funding here’s the perfect system”, but came from people without… standing, or an understanding of the current landscape, and especially how to change the landscape to make their proposal possible
- “ideas are cheap execution is everything”
- Wish more people wrote about their work
- When judging, I still feel anchored on existing people/writers I know are good, rather than having discovered new ones
- Idea: some way to just force existing defunct writers to write again
- ACX Book Reviews contest does hide the author, maybe that helps
- Jenn: “writing for someone else sucks the fun out of it” (?)
- but also, constraints breed creativity
- also, hoping that a bunch of people wanted to write something like this already
- Next time, could skip the open call (only take submissions from whitelisted people?)
- Though, many of the best weren’t Inkhaven but like, other people I knew, so idk
- Mysteriously, writing is more compelling when it’s not bullet-pointed. See dynomite on formatting.
- I think Jenn and Chris’s submission suffered a bit for this, in the end
- Maybe just throw the bullet points into Claude and ask them to take them out for you
- (bullet points are nice for quick reorienting of the structure of the thinking, esp in something like Notion. you can get an at-a-glance view of)
- Not that many Inkhaven submissions, so for this prize specifically maybe not that necessary
- Of course, we wanted to sponsor Inkhaven for other reasons, ie because they’re producing great writing overall and we want to support that, and because we want to BRAND in front of a bunch of promising writers
On designing this competition
- Not sure how bad the 1 week timeline to submit was
- Good: move fast, get a bunch of things out, maybe can iterate on substance/style in the future
- Bad: a lot of essays seem half-baked compared to what could have happened
- Also the grading is super rushed, rip
- next time get an LLM grader up too
- (and LLM feedback-er so essays can be improved?)
- Was it good to accept LLM submissions?
- sure made a bunch more work for me. I ended up desk rejecting about half of the submissions
- Word counts, was 500+ good?
- Maybe should have limited from 500 to 2000 words?
- Other structures/competitions that might be fun:
- Best tweet
- Best infographic
- Best shortform video
- Best microsite
- Highest performing (views, engagement) <piece of content>
- <various goodhearting concerns>
- Most money raised on sales/substack subscriptions
- Next step: maybe get some editing feedback to the top essays to prepare to publish? (Maybe we can lean on Inkhaven writing advisors for this?)
Why host an essay competition?
(somewhat overlapping)