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DL 418

Building in Plain Sight

Liberating 400+ Issues from Platform Capture

Published: January 25, 2026 • 📧 Newsletter

Hey all. For the past year or so, I've been working on something that represents both a technical project and a philosophical commitment. Transforming the entire Digitally Literate archive into a digital garden.

This is the story of how I did it, why it matters, and what I learned about AI, voice, and digital autonomy along the way.

If you've found value in these issues, subscribe here or support me here on Ko-fi.

🔖 Key Takeaways

📚 The Problem: When Knowledge Gets Trapped

For years, friends would ask me about the newsletter and say some version of the same thing: “Have you ever thought about stepping back and looking at it as a whole?” A few even suggested I should do a thematic or longitudinal analysis to trace how the ideas changed over time.

At the same time, I found myself asking friends far smarter than me a different question: “Have you ever thought about building your own wiki?”

What I was really circling was structure. I kept imagining a space that could hold ideas side-by-side instead of stacking them in a line. Something that could mimic a wiki. Not in the encyclopedic sense, but as a way to show how thinking evolves.

As I sat with that idea, it clicked. What if the newsletter was just one input?

What if I could plug in the newsletter and blog posts, and reading notes, and presentation materials. What if I could share not just polished outputs, but the notes, the connections, the half-formed ideas. All while letting folks see how the dots got connected.

That question kept nagging at me, especially as we’ve moved deeper into a moment flooded with AI-generated slop. Perfectly smooth. Perfectly forgettable. Disconnected from any real thinking process.

Over the years, I’ve published more than 400 newsletter issues. They lived on platforms like MailChimp and WordPress. Each one was convenient at the time, and each one quietly boxed my work in.

Technically, the content was mine. Practically, it wasn’t. It lived inside systems I didn’t control, locked into formats that didn’t talk to each other. Old ideas sank out of sight. New ones piled on top. Nothing connected.

That became obvious a few years ago when a tech company asked if I had a knowledge base behind the newsletter.

I didn’t. I had a stream.

Newsletters are great at delivering ideas in the moment. They’re terrible at helping ideas grow over time. I couldn’t easily link themes across years. I couldn’t surface recurring ideas. I couldn’t build explainers that connected insights from 2018 to reflections from 2024.

I needed the newsletter to be a web, not a feed.

That’s when I started looking seriously at digital gardens. Not as another platform, but as a way to reclaim control, slow things down, and make thinking visible again.

🛠️ Getting the Work Back

Step One: Get Everything Out

The first thing I did was download every newsletter archive from MailChimp and MailPoet. Years of work, mostly trapped in HTML emails and databases.

Then I used AI (Claude) to help me figure out how to convert all of it into Markdown using Python.

Why Markdown? Because plain text lasts.

You can read it without special software. You can back it up anywhere. You can version it, move it, remix it. When platforms change, or disappear, plain text survives.

AI didn’t replace the work. It compressed it. What would’ve taken weeks took days. The key wasn’t knowing everything up front. It was knowing where I wanted to end up.

🧵 Finding the Thread

Once everything was in plain text, I could finally see the newsletter as a whole.

I could trace its evolution, from TLDR-style curation to deeper analysis. I could see patterns in what I kept returning to. The core ethos became clearer:

The newsletter index now shows that arc. Not just what I wrote, but how my thinking changed over time.

🌿 Structure That Creates Pathways

Inside Obsidian, I added simple metadata to each issue: title, date, tags, and links to related ideas.

This is where the “garden” metaphor really clicked. Instead of organizing files, I was creating paths.

Obsidian lets you link to ideas that don’t exist yet. These “ghost pages” act like placeholders. Notes to your future self. When I tagged an issue with something like digital autonomy or surveillance capitalism, I could link to a page that I knew I’d eventually want to build.

The goal wasn’t perfect explanation. It was connection.

⚠️ The Voice Problem

AI was incredibly useful for cleaning things up like formatting, metadata, consistency. But it also kept trying to sand down my voice.

Every suggestion to “improve” phrasing came with a quiet risk. Questions about Is this still me?

I ended up drawing a hard line:

It can help organize thoughts. It shouldn’t replace them.

That boundary took work to maintain. But the newsletter only matters if it sounds like a human thinking out loud, not a system optimizing content.

🌱 What the Garden Makes Possible

Now that the full archive lives in the digital garden at digitallyliterate.net, something new is possible.

You can follow ideas across time. You can see how my thinking about AI shifted. You can trace themes as they develop instead of watching them disappear into the past.

Each issue links to related concepts. Quotes connect to the people who said them. Ideas stack, branch, and return.

This isn’t just better organization. It’s ideas being allowed to compound.

Instead of scrolling endlessly, readers can follow curiosity. Choosing their own path rather than being pushed along a timeline.

🔧 Where It’s Headed

Right now:

Next up:

Because platforms don’t fail if. They fail when.

Why This Matters

This project isn’t separate from what I write about. It is the argument.

The digital garden isn’t finished. Gardens never are. But now the shape of the work is visible.

Ideas can talk to each other. Thinking can stretch across years. And that feels worth the effort.

🤔 Consider

The garden is the web as topology. The web as space. It's the integrative web, the iterative web, the web as an arrangement and rearrangement of things to one another.

— Mike Caulfield

We've spent years documenting how platforms promise permanence while building for obsolescence. How convenience becomes capture. How corporate infrastructure extracts value while concentrating control.

Building alternatives requires different principles. Not platforms that might honor their promises, but infrastructure you control completely. Not formats that require specific software, but plain text that outlasts proprietary systems. Not chronological streams where content disappears, but interconnected gardens where knowledge compounds.

The technical work of converting 400+ issues to Markdown and building an Obsidian vault isn't separate from the editorial work of analyzing surveillance capitalism and digital literacy. They're the same work. Understanding the systems that extract and control is necessary. Building the infrastructure to resist them is essential.

This newsletter has always been about capacity-building. First for staying informed (TLDR), then for critical analysis (Digitally Literate), now for genuine autonomy (the digital garden and InitiatED). Each evolution builds on what came before rather than replacing it.

The garden makes that continuity visible. You can trace how ideas develop across time, how early observations become deeper analysis, how understanding leads to infrastructure. The connections aren't just convenient, they're constitutive. They show how knowledge actually works.

⚡ What You Can Do This Week

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