Migrating from Obsidian Publish to an Astro Blog

Obsidian is a genuinely strong tool for personal wikis and writing, and if you care about Zettelkasten or documentation, it’s the editor most people recommend these days. I never warmed up to Notion, and Roam Research always felt a bit unwieldy to me. As Obsidian started turning into the de facto standard in this space, I made the jump and committed hard. I even paid for Obsidian Publish and migrated my whole blog over from gatsbyjs, which had been working fine.

Deployment was fast, the site design was decent, and writing was comfortable. I switched over around 2023 and managed to ship a few retrospectives along the way, so it earned its keep. But using Obsidian Publish as a blogging platform turned out to be rough in a lot of small ways. The biggest issue was SEO. My old gatsbyjs blog had a steady stream of organic traffic, and after I moved to Obsidian Publish that traffic basically evaporated. If I wanted someone to read a post, the best option was to send them the link directly. Even for a blog I write mostly to scratch my own itch, having readers and not having readers are very different things.

It’s file-based and doesn’t enforce frontmatter. Once you add Obsidian sync and Publish, the price climbs. Custom things like Google AdSense and event tracking aren’t supported; you’re stuck with whatever Obsidian itself ships (like GA). And the biggest pain point is the lack of a comment feature. Not that anyone was lining up to comment, but I do have at least a small soft spot for a bit of back-and-forth, and the silence wore on me.

Even so, I wasn’t writing that often, and Obsidian was comfortable enough that I kept using it. But now that I’m a free agent, what’s left is the record I leave behind, and the record is the writing itself. I wanted to take it more seriously, so I moved again — this time to an Astro-based blog platform.

That makes Restarting Blogging date back to November 2019, and Blog Migration (Gatsbyjs to Obsidian Publish) to late December 2023. Looking at that first post, my real blogging history goes back to Octopress, then Jekyll, Gatsbyjs, Obsidian Publish, and now Astro. Five platforms in.

(I’m the kind of person who buys a notebook and pen before studying, or researches gear before working out, so my way of expressing intent is always pretty noisy.)

Astro bills itself as a web framework for content-driven sites, and it seems to power not just blogs but e-commerce and other kinds of sites too. Rendering is fast, SEO is configurable, SSR works, and a lot of upsides surfaced when I evaluated it. I’m using a theme right now, but I figured I could customize it myself down the line, so I picked it. The other candidate I looked at was Hugo, built on Golang. I judged Astro to be more extensible, so Astro it was.

The thing that gave me the most trouble during the move was converting Obsidian’s folder-tree markdown files into a flat structure. I wrote a few automation scripts with Codex and ran the migration that way. And surprisingly, since Obsidian doesn’t carry frontmatter (the post metadata), I had to look up the creation date of each old file and rewrite the format one by one. That was probably the hardest part. Thankfully — if you can call it that — there weren’t that many posts, so it went quickly enough…

Since leaving the company, I’ve been on a “leave AWS behind” kick for a while and started using CloudFlare. CloudFlare Pages even supports Astro-specific deploys, so the deploy itself took maybe five minutes, and I added a few more conveniences with scripts.

Stack

• Astro
• CloudFlare Pages
• Github (with giscus comments)
• Decap CMS (not yet. Would the headless CMS editing experience even be good? Wouldn’t it be easier to just write in a markdown editor and convert?)
• Google Analytics / Posthog (always wanted to try it, so why not now)

I’ve been posting to Threads here and there too. I want to keep jotting down the non-retrospective stuff, the thoughts that drift through my head.

Let’s go (or so I tell myself).