June 2026 Writing Challenge Post Mortem
For the last month, I have been making approximately one long form post per day. I challenged myself to write something every day in June, as an exercise and to get back into the habit of writing. Even though I narrowly failed the challenge, it still achieved most of my goals, and provided some unexpected useful insights as well. I made 28 posts in 30 days, missing four days and having two double-post days. Most of the missing days were spent on legal drafting; I had intended to post motions and memoranda a few times in the month to fill the gaps, but instead ended up spending 35 hours on a single motion that still isn't finished.
Every post, with a few unimportant exceptions, was posted in its entirety to Facebook, Substack, Dreamwidth, Reddit, Glosso, and Paper.wf. Every post was summarized and linked on Twitter, Threads, Bluesky, and Mastodon.social. This is the first time I've done such widespread cross posting, which led to somewhat depressing realizations regarding engagement and reach, which I'll describe later. Wherever you're reading this right now, you can probably find all of the others if you scroll back/up/down/whatever on my profile.
The biggest category I'd sort my writing into is a combination of communication, awareness of how the world works, decision making, and interpersonal interactions. “What to do when my questions indicate I'm more informed than you think?” and “Rooting out fundamental disagreements with hypothetical questions” are attempts to better connect with people who seem to misunderstand certain conversational patterns. “We need a way to ask Maybe/No questions” is about a pattern that's difficult to convey at all. “Cheating is breaking rules that you agreed to” aims to analogize game cheating with relationship cheating. “Why write about a pattern without actionable followup?” describes a pattern in my writing that people express confusion about. “You feel [verb]ed? That's also an accusation and request.” is trying to help people understand how what they say can convey more than they intend. “Low success rate does not require low skill” and “Some choices are net positive despite increasing negative outcomes” are attempts to address common misconceptions about particular relationships between choices and outcomes. “We need to popularize “anti-” as an alternative prefix to “a-”” is a proposal to stop using some ambiguous terms in self identification.
Coming in second was intentional community, in general and my experiences and my future plans. Those posts included “Doing chores is a normal part of living alone and it gets easier together”, “Lessons from Estate of Mind”, “Hunting for improved real estate for a large intentional community”, “Setting community norms democratically within dictatorial bounds”, “Events that I want to fit at my next place”, and “Adventures in parenting 20-40 year old teenagers”. “My Ideal Day” is ostensibly about me, but it's really a description of a slice of the community environment I hope to build, and I even illustrated some of the posts with an aspirational schedule for CoDwell that I sketched out years ago. A few of these are topics I've written on before and approached with some years of additional experience this time. A few are strictly forward looking. When it comes time to launch CoDwell or some other next big intentional community project, these posts will serve as source material for putting together the thoughts and ideas that I want to share with people who seem interested in collaborating.
Another common theme was the law. “Legal Situation Update” and “I still need a lawyer” specifically covered my current situation and outlook. “The tyranny of civil court clerk delays” is a not very successful attempt to explain a problem with court rules and deadlines. “How I search for professional assistance” describes how I've tried to find a lawyer, which is also the process I've used to [fail to] find a plumber, a side loader rental, etc.
I made two posts about some failures I've had when trying to work for FAANG companies. “An impossible first task at Google” describes how a confluence of policy changes and management missteps wasted my first few months of effort there. “Ruinous Surprises in Company Culture” was prompted by some comments on the earlier post, and describes some ways ICs are expected to interact with each other and managers at Google and Amazon, but which are conspicuously absent from any new hire onboarding.
That leaves a bunch of miscellaneous posts. “Accurate Confidence is a Trainable Measurable Skill” is trying to explain and expose people to the idea of confidence and confidence calibration. “The internet peaked in 2008” describes a bunch of aspects of being online that have gotten much worse in the last 15-20 years. “Most people don't understand giving 100%” laments that so many people find working (or thinking) to exhaustion to be entirely alien. “More local monopolies deserve limits on the right to deny service” suggests that Uber (among others) shouldn't be able to fire a customer. “My online projects that need more hands” describes three things I've tried to do online which haven't really taken off. “Instant communication and fast travel worldwide is a fad” is a shower thought about our world effectively shrinking for the last 100k years, a trend which will reverse as soon as we start living on the Moon and/or Mars.
The final category is two meta posts, “June 2026 Writing Challenge” made on May 31 to describe what I'd be doing, and this “June 2026 Writing Challenge Post Mortem” today on July 1.
On a positive note, this did renew my love of writing long form posts. I don't know if I can maintain that enthusiasm with so much less engagement today than I had 10-20 years ago, but I'm going to try! I'll be looking for inspiration in others' posts and perhaps trying to figure out the Substack ecosystem a bit better. I may also subscribe to Twitter to extend my reach there; I'd like to be better connected to my friends of friends who post and correspond mostly there.
Also, I made a few new friends, and reconnected with some folks I haven't heard from in years. That's always a possibility when posting a new long form thing, and posting a bunch of them really accelerated the process. TBD what comes of this, but I anticipate some positive downstream effects, and maybe even some IRL [re]connections.
The most annoying takeaway from this challenge is that Facebook remains the platform where I can find the most engagement. I don't mean modern influencer “engagement” metrics; I mean literally actually engaging with other people. I post something, they comment, I reply, they reply, eventually one of the replies spills over to a top level post on their wall, I comment there, etc. With 29 posts, I got about 300 comments across all platforms, 196 of which were on Facebook (not counting my own replies). One post there was shared 63 times, but I haven't tracked down the shares to find more comments yet. FB also accounts for a third to half of my total views across all platforms. I was really hopeful that I'd be finding more interaction after a couple of years of connecting with old friends and finding new followers on other platforms, but even Twitter still feels sorta dead to me, let alone less popular platforms. The one exception among other platforms is Reddit, where I find more than a little discussion when I can find a topical subreddit that accepts cross posts, but that only works out for a small fraction of the things I write.
Another sad realization is that I am less capable of critical thought and research and deep writing than I was 20 years ago. I can still do a good job occasionally, but there's no way I could sustain this pace of posting with even this low level of quality, let alone what I was capable of in college. In addition to scraping the bottom of the barrel for post topic ideas, I also did a not great job of both writing and editing. This is just another item on the checklist of long term cognitive decline, and I've been aware of it for a while, but rarely with such stark examples.
I'm also mildly disappointed that I wasn't able to attract attention from acquaintances who participated in Inkhaven. One of the reasons I postponed this challenge until after that event was in the hope that a little bit of what folks had learned there would rub off through their feedback. Maybe next time!
Overall, this was a positive experience, and I'll probably do it again at a less hectic point in my life. I am definitely not in top form lately, and maybe I can recover some of my capabilities after some down time. Thanks for coming along for the ride!