In 2004, John Gruber published Markdown — a text-to-HTML conversion tool for web writers. The name was a joke: “markup” is what HTML does with its angle brackets and tags; “markdown” inverts that. Simpler formatting for regular writing.

Gruber’s overriding design goal: a document formatted in Markdown should be readable as-is, as plain text, without looking like it’s been marked up with tags or formatting instructions. The syntax was inspired by the one structured format everyone already knew — plain text email. Asterisks for emphasis, dashes for lists, blank lines between paragraphs. Conventions people had been using for decades before anyone called it a format.

Aaron Swartz — 17 at the time, already building RSS and later Reddit — was Markdown’s sole beta tester. Anil Dash described him as “a total pain in the ass, which made him terrific at reporting bugs in your software.” Swartz shaped the syntax through feedback and built html2text, a tool for converting HTML back into Markdown. The collaboration was unpaid. Gruber released it freely — 2004 internet ethos, building for the good of the web.

Twenty-two years later, Markdown is the default format for GitHub, Reddit, Discord, Obsidian, Stack Overflow, and Slack. Developers document in it. Writers draft books in it. Researchers publish papers in it.

WordPress might not exist in twenty years. Medium already pivoted. Substack could shut down. Your markdown files will still open in any text editor on any operating system.

That’s not an accident. It’s a consequence of what markdown won’t let you do.

#Constraints as Mechanism

You can’t change fonts in a markdown file. You can’t set colors, adjust spacing, or build complex layouts. These sound like limitations. They’re the reason your content works everywhere.

Every feature a format adds is a potential lock-in point. Custom fonts require the rendering engine that supports them. Complex layouts require the tool that created them. .docx needs Word. .pages needs Apple Pages. .gdoc needs Google Docs.

Markdown needs a text editor. Every computer has one.

The things markdown won’t let you do are precisely the things that lock content into a single tool or platform. Constraints aren’t the price of simplicity. They’re the mechanism that enforces portability.

This separation — content and structure in the file, presentation decided by whatever renders it — means the same markdown file can become a web page, an email, a PDF, or a slide deck. Change your blog’s design without touching your content. Switch publishing tools without converting a single file. The content is immune to the tool.

#The Survival Test

HTML has been around since 1993. Plain text has been around since computers existed. Markdown is both — plain text that converts to HTML. Two of the most stable formats in computing, composed.

Derek Sivers has run sive.rs on plain text for decades. No CMS. No database. Text files rendered to HTML. He’s published books, built companies, written hundreds of essays — all from plain text. The lesson: the simplest formats outlast the sophisticated ones. Not because they’re better in any given moment, but because they have no dependencies that can break.

When you invest years of writing into a format, the format’s longevity is the most important feature. Every CMS that exists today will eventually change, pivot, or disappear. Your markdown files won’t notice.

#AI Speaks Markdown

An argument that didn’t exist two years ago: AI writes markdown natively.

Copy text from ChatGPT or Claude — it’s already formatted in markdown. Headings, bold, code blocks, lists. Paste it into your blog and the formatting is correct. No cleanup, no conversion. Feed your markdown draft to an AI for editing — the feedback comes back in the same syntax, ready to merge.

Markdown has become the lingua franca of human-AI text exchange. Not by design — by selection pressure. It’s the simplest structured format that both humans and machines read naturally. The same properties that make it good for people (readable, portable, lightweight) make it good for AI.

If you’re choosing a format for writing that will matter in ten years, bet on the one that both humans and machines already converged on independently.

#The Bet

Markdown is a bet that content should be independent of its container. That the format you write in should outlast the tool you write with. That constraints which prevent lock-in are more valuable than features that enable it.

It’s a bet that’s been winning for twenty-two years. For a deeper look at the syntax, there’s a guide. To turn your markdown files into a blog, start here.