I have a lot of nostalgia for the era of blogging that I grew up with during the first decade or so of the 2000s.

Of course there was a ton of great content about technology and internet culture, but more importantly to me it was a time of great commentary and experimentation on the form of blogging and publishing.

As social media and smartphones were weaving their ways into our lives, there was a group of bloggers constructing their own worlds. Before Twitter apps and podcast clients became the UI playgrounds of most designers, it was personal sites and weblogs that were pioneering the medium.

Looking back, this is probably where my meta-fascination with the web came from. For me the most interesting part has always been the part analyzing and discussing itself.

Robin Sloan puts it well (as he is wont to do):

Back in the 2000s, a lot of blogs were about blogs, about blogging. If that sounds exhaustingly meta, well, yes — but it was also SUPER generative. When the thing can describe itself, when it becomes the natural place to discuss and debate itself, I am telling you: some flywheel gets spinning, and powerful things start to happen.

Robin Sloan, A year of new avenues

Design, programming, and writing started for me on the web. I can recall the progression from a plain text editor to the Tumblr theme editor to learning self-hosted WordPress.

All of that was driven by the desire to tinker and experiment with the web’s form. How many ways could you design a simple weblog? What different formats were possible that no one had imagined before?

Earlier this week I listened to Jason Kottke’s recent appearance on John Gruber’s podcast and was delighted to hear them discuss this very topic. Jason is one of the original innovators of the blog form, and I’ve been following his blog,, since I was old enough to care about random shit on the internet. turned 25 years old this week, and Jason has been publishing online for even longer than that. All along the way, he has experimented with the form of content on the web. He’s not alone in that—many bloggers like him have helped to mold the internet into what it is today. The ones that influenced me besides are Daring Fireball,, Jim Coudal and Coudal Partners, Shawn Blanc, Rands in Repose, Dave Winer, and more that I’m certainly forgetting.

A screenshot of from October 12, 1999, and my personal favorite design of the site over the years

Jason and John have an interesting conversation during the podcast (starting around 25 minutes in) about how the first few generations of bloggers on the web defined its shape. Moving from print to digital mediums afforded a labyrinth of new avenues to explore.

It’s always important to remind ourselves that many of the things we take for granted today on the web and in digital design had to be invented by someone.

Early weblogs did not immediately arrive at the conclusion of chronological streams—some broke content up into “issues”, some simply changed the content of their homepages entirely.

It wasn’t until later that the reverse-chronological, paginated-or-endless scrolling list of entries was introduced and eventually became the de-facto presentation of content on the web. That standard lives on today in the design of Twitter, Instagram, etc., and it’s fascinating to see that tradition fading away as more sites embrace algorithmic feeds.

By the way, I’d be remiss here if I didn’t mention Amy Hoy’s amazing piece How the blog broke the web. Comparing the title of her piece with the title of this one, it’s clear that not everyone sees this shift in form as a positive one, but she does a great job in outlining the history and the role that blogs played in shaping the form of the web. Her particular focus on early content management systems like Movable Type is fascinating.

Another great example that Jason and John discuss on the podcast is the idea of titling blog posts.

They point out that many early sites didn’t use titles for blog posts, a pattern which resembles the future form of Tweets, Facebook posts, text messages, and more. But the rise of RSS readers, many of which made the assumption that entries have titles and design their UIs around that, forced many bloggers to add titles to their posts to work well in the environment so popular with their readers.

Jason mentions that this was one of the driving factor for to start adding titles to posts!

This is an incredible example of the medium shaping the message, where the UI design of RSS readers heavily influenced the form of content being published. When optimizing for the web, those early bloggers and the social networks of today both arrived at the same conclusion—titles are unnecessary and add an undue burden to publishing content.

This difference is the very reason why sending an email feels heavier than sending a tweet. Bloggers not using titles on their blog posts figured out tweeting long before Twitter did.

When referring to the early bloggers at, Jason said something that I think describes this entire revolution pretty well.

[…]there was in information to be gotten from not only what they linked to, but how they linked to it, which word they decided to make the hyperlink.

Jason Kottke on The Talk Show episode 370 (35:40)

It’s not often that you have an entirely new stylistic primitive added to your writing toolbox. For decades you could bold, italicize, underline, uppercase, footnote, etc. and all of a sudden something entirely new—the hyperlink.

With linking out to other sites being such a core part of blogging, it’s no surprise that the interaction design of linking was largely discussed and experimented with. Here’s a post from Shawn Blanc discussing all the ways that various blogs of the time handled posts primary geared towards linking to and commenting on other sites.

Another similar example is URL slugs—the short string of text at the end of a web address identifying a single post. For many of my favorite bloggers, the URL slug is a small but subtle way to convey a message that may or may not be the same as the message of the post itself. One other stylistic primitive unique to the web.

The different ways in which bloggers designed their site or linked to words became a part of their unique style, and it gave their each of them an entirely new way to express themselves.

It’s hard to communicate how grateful I feel for this era of experimentation on the web, and specifically for Jason Kottke’s influence on me as a designer. The past 25 years have been a special time to experience the internet.

There was a time when I thought my career might be curved towards blogging full-time and running my own version of something like Through exploring that I found my way to what I really loved—design and software. My work continues to benefit from what I learned studying bloggers and publishers online.

Whether you care much about writing or not, I encourage you to have a blog. Write about what interests you, take great care of how you present it to the world, and you might be surprised where it takes you. There are new forms around every corner.