Exploring Reddit essays

Welcome to my weekly newsletter about practical ways to make the Internet better, focused on my own work in that space. I'm Jacob O'Bryant.

Quick announcement: after four years of entrepreneurship, I've finally decided it's time to rejoin the land of the employed. See my resume if your workplace needs someone with codin' experience.

I guess I should also say that my work on this newsletter, Yakread, and tools for online speech in general will continue without interruption; it'll just happen a bit slower 🙂. I'll continue to grow Yakread organically on the side, and maybe down the road it'll get to the point where I can resume working on it full-time.

That being said, I also like the idea of finding ways to continue my TFOS work without even trying to structure it as a full-time business. For example, last month I mused about starting some kind of nonprofit; yesterday I had an "oh duh" moment and realized that I could start out by looking for existing projects/organizations to donate to and write about.

Over the next four years, I'd like to do more of the exploration for exploration's sake that I spent so much time on as a teenager.

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I've been thinking recently, as one does, about how to do marketing for my work and ideas. I don't need lots of subscribers. At the same time, I don't want to be a complete digital hermit. I want to keep meeting new people and be part of a community that I can contribute to.

My current plan is to just write really good essays, somewhere between once a month and once a quarter. At the same time, I'll continue to read a lot and search for other people who are interested in the same things as me. Then I can always just send them links to my essays and ask for feedback directly. No need to overthink it 🤷‍♂️.

As such, I'm giving myself permission to not even try to get into the habit of posting regularly on Substack Notes or what-have-you. Tweets just aren't my thing. I did go through all the trouble of setting up a Substack account for that purpose, but instead of posting there often I'll probably just use it as a place to host any Substack-focused essays I write.

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I made a TFOS subreddit. I haven't posted much there yet; I just wanted to play around with it a bit and see if I might like it more than Discord. I was actually pleasantly surprised. I think Reddit's history of doing user-hostile things blinded me somewhat. But, I mean, it's got pretty much everything I want—asynchronous structured discussion, chat, easy to set up, public (no need for invite links!), there's even RSS—and I'm guessing that of the people who read this newsletter, more are familiar with Reddit than are familiar with Discord. Also Reddit has better moderation tools.

So yeah, if you're thinking about places to host a community/places to host comments for your newsletter, maybe give Reddit some consideration. I'll start writing my "lab notes" on Reddit next time I'm in a thinking mood, and after that maybe I'll transition from Discord to Reddit more generally.

Might as well throw in a Reddit link for this post!

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Links now presented in purely random order 🙂.

Product-Led Anxiety [Skeptocapital]

Looking for Alice [Escaping Flatland]

ReadWriteWeb Turns 20 [Cybercultural]

The Value Of Links In 2016 [Richard MacManus]

Remembering GitHub’s Office, a Monument to Tech Culture [Nadia Asparouhova]

Scraping training data for your mind [Escaping Flatland]

ICSI: changing lives (but not a VC’s) [Skeptocapital]

“Where have all the hackers gone?” + a way to discuss programming languages [More Pablo]

How we Build Platforms [Mark Nottingham]

“Boring” is just one strategy [More Pablo]

Social Networking — Past, Present and Future [Cybercultural]

Building new cultures [Escaping Flatland]