• 17 Aug, 2025*

It’s a fair question.

I already have a personal blog where I’ve occasionally published some stuff over several years. There was one before that too, which no longer exists, though I think I moved some of the posts over.

I have a blog for my business. There’s this newsletter on tech and AI, which I decided I didn’t want to focus on anymore. I also have this other newsletter about making buildings work better, which is similarly neglected. Then there’s this defunct family travel blog that I ham-handedly moved between hosts many years back, breaking a bunch of links and losing photos.

I clearly love starting writing projects. What I’m trying to do here is to create one I can stick with.

One thing all of these previous undertakings have in common is their complexity (at least in my mind—and since that’s where the writing comes from, or doesn’t, that’s what counts).

I’ve always focused a lot on aesthetics. I fiddle with layouts and themes instead of writing. I ruminate on the best workflow for processing photos and then optimizing my system of renaming, resizing, and compressing them for the web. This all takes a lot of time away from actually creating the content itself.

Then there are the platforms. I’ve been a Wordpress user for over a decade and love the software in many ways. In other ways I find it bloated and overkill for what I really want and need. I’ve tried Substack, and I also use the newsletter feature on LinkedIn. I’ve written on X.

All these platforms are fine and they’re all the same in one important way: they’re rife with distraction if what you really want is words on the page.

I’ve tried addressing this by writing in focused writing apps like iA Writer, which is one of my favorite pieces of software of all time. But iA Writer doesn’t put words on the internet. So then I have more steps: export or copy/paste, reformat, add photos, proofread again, make edits (in two places now)... why am I doing this again?

Now I’ve discovered Bear Blog. I think AI told me about it, which is funny because part of my current motivation for writing is a craving for human creativity and art, human imperfection, and human diversity of thought and opinion. I feel both a desire and obligation to contribute my little bit. I was immediately drawn to the minimalist aesthetic, open web principles, and aspirations for long term durability of the platform.

And then I got distracted by the idea of coding a website from scratch in plain HTML and CSS. Wouldn’t that be cool? Why not, right? Let’s go old school. It would just be basic text files, in a basic file tree, readable by any computer from the 1980s to the 20-whatevers. Hosting would be cheap and the whole thing would be easily transportable should there ever be any issues with one provider or another.

Posting would be easy enough... it’s just plain text. So I would simply write in markdown in iA (or whatever), export to HTML, copy/paste into a blog post template in VS Code (or whatever), fill in the date and any other fields, check all the HTML (thanking God for syntax highlighting), save as generic “index.html” (since I want to hide the “.html” in the url), create a folder with the blog post title on the server, upload the “index.html” file via FTP, add a link from the main blog archive page, and Bob’s your uncle!

That seems 100%, totally sustainable... right?

It was right around here that, in a somewhat numinous experience, I stumbled on this post which felt like a bucket of clear, refreshing, back-to-my-senses cold water being dumped on my frazzled head.

...if you are struggling to blog now with a text box on a website that handles it all for you, what makes you think selfhosting and having to use the CLI to get some SSG to build it will get you to blog more?

...OK, fair enough, but...

It’s acknowledging that it’s probably not the tool holding you back, it’s something in your real life, your environment maybe, or your mindset. Or it’s simply your natural limits that you should honor.

...yeah, totally, but...

You don’t seem to recognize that constraints are actually advantageous for someone like you, so you can even focus on putting stuff out or writing that todo without constantly changing design, functions, tags or fixing bugs and burning out on it.

You win. That is all exactly correct.

So here I am, intentionally choosing simple. Intentionally imposing constraints in an effort to create freedom.

Will it work? Time will tell.

Thanks very much for reading.