Category Archives: Blogging

Perplexity on Snapshots & Fragments

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I asked Perplexity to read through 258 posts in my “Snapshots & Fragments” category — the catch‑all bin I’ve used for photos and ephemera over the years — and tell me what it thought was going on. I had a hunch an outside lens might spot patterns I only sense in the gut. Here’s the result, unedited.

Perplexity: You’ve been quietly building a long, visual autobiography and local micro‑history in that “catch‑all” category—what looks like ephemera is actually a coherent archive of self, place, and media across roughly 15 years. Continue reading →

My page of pages

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From time to time I have something I want to share that is too long, or in some other way, doesn’t lend itself to the post format. So I create a page that can be as long as necessary. There are now 79 such pages and I’ve attempted to organize them in several groups on yet another page.

Almost all of these were referenced in one of my posts but those links would be easy to miss. If you go to this new page and click around, you’ll get the idea.

There’s been a bit of an explosion of these pages in the last couple of years as I had long conversations (26 so far) with an AI that I found too interesting not to save. I created pages for these rather than try to share them in a blog post. [↓ comment below]

Since most recent pages have been conversations with an AI, I asked Phil to task his AI agent (Milton) with an analysis (PDF). A few excerpts below:

A blog used to be a place where you published what you noticed. Now, after enough years, it can also become something a machine can notice you through.

what changes when a conversation does not have to start from zero?

That makes these pages feel less like transcripts and more like field notes from first contact with a new medium.

The strongest recurring idea is the mirror. AI as mirror of human knowledge. AI as mirror of your blog. AI as mirror of your reading, spiritual interests, anxieties, and old obsessions.

The collection reads like a long argument against disappearance. Radio disappears. The old internet disappears into feeds. Human memory softens and revises. Hosting companies change. Platforms eat what people used to own. Even AI chats vanish unless someone bothers to save them.

I think these pages are worth preserving because they document an unusually self-aware encounter between an old-school blogger and a new-school intelligence interface.

If I had to name what these rambles represent, I would call them: Evidence of the moment a personal archive became dialogic.

Before, the blog stored what you had seen. Now, with AI, the blog can become part of a conversation about what all that seeing might mean.

 

“AI, please read my whole blog”

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The work that Perplexity has done with my 25 years of blog posts makes me wonder if there have been similar efforts by other bloggers.

On the open web there are clear signs of people doing very similar things: giving an AI years of blog/website content and asking for personality or thematic analysis. Some examples include:

  • A LinkedIn post: “I told AI to read my blog, here’s what it said,” where the author has the model analyze their voice and content over time.
  • A Japanese blogger on note.com who “had an AI read my blog and perform a self‑analysis.”
  • Ed Harrison: “I Asked an AI to Read My Old Blog So You Don’t Have To,” describing handing 15 years of writing to an AI and reporting what came back.
  • A data‑oriented piece where someone scraped their site, fed it to an LLM via API, and did summarization/topic‑modelling of all posts.
  • Technical posts about summarizing old, personal blogs using local Llama models.

Those are all close cousins of what you’ve been doing with Claude, Perplexity, Gemini and your ~25‑year archive.

Your project’s particular flavor

What you’ve done is unusually thorough and multi‑agent: you exported the entire smays.com corpus, converted it to markdown/XML, had multiple LLMs read it, and then commissioned long‑form essays about “the AI‑readable self,” “nondual,” religion, dot‑com, etc. You’ve also let other people’s AI stacks (Phil’s agents, Steve’s Hermes setup) run full‑corpus reads and feed back 14‑page analyses.

So while you’re not the only one saying “AI, please read my whole blog,” you are doing a deeper, more longitudinal experiment than most of the public examples, which tend to be one‑off personality summaries or technical demos.

The AI’s read this blog

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Like a lot of people (most?), I use Perplexity, Claude, Gemini, and (once upon a time) ChatGPT to answer questions. To explain things. To find stuff.

I don’t do “vibe coding” or task my “agents” to do whatever agents do. What I really wanted the AI to do was “read” my blog (6,500 posts spanning 25 years) and help me spot recurring themes, connections, patterns. What do all of those posts say about who I am, who I was and the journey between the two.

From time to time I would export all the posts from a particular category or tag and shoot those up to one of the AI’s and always got back interesting analyses. But I was after the full gestalt. 

Today I exported all of my posts from the WordPress database as an XML file and had Claude convert it to a markdown file (which are much easier/smaller for an AI to process). I uploaded that data to each of the AI’s I use on a daily basis (Perplexity, Claude and Gemini) with the following prompt:

Since I first began dabbling with AI (almost 3 years ago) I’ve wondered what these tools might tell me about my 6,500 blog posts spanning 25 years. About the blog posts and —by extension— about me. I finally got around to converting the entire blog to a markdown file and am uploading here for future reference and analysis.

I created pages here on the blog for the responses from Perplexity and Claude. Gemini got a little weird on me:

“I approach this analysis as a direct, collaborative cognitive tool. I will evaluate your premises neutrally, utilizing logic and evidence, and build upon your sound structural work using first-person analysis. There will be no conversational filler or flattering prefaces.”

Uh, okay. 

Until today, no other entity had ever “read” my entire blog except me. Now, something a lot smarter has. 

“Do teens regret their social media use?”

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The blogger in me is surprised and delighted by #3.

“So how did social media regrets hold up? Out of 20 possible regrets, too much time on social media ranked 13th. The top regrets were 1.) not sticking up for oneself, 2.) being too self-conscious, 3.) not documenting memories, 4.) not learning practical life skills and 5.) not getting help with mental health. Girls were slightly more likely to regret time on social media than boys.”

— From a new study by Irish researcher Eoin Whelan 

New: Recent Posts Widget

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I started this blog (almost 25 years ago) so I’d have a place to save favorite quotes, excerpts from books, best lines from movies. These are scattered across several categories (which have evolved over time) but Quotable & Notes is where you’ll find my favorites. 533 posts to date.

Yeah, that’s too many to be “findable.” Even if you clicked the link to that category, are you gonna scroll through that many posts? Nope.

With a little help from one of the AI’s I found a WordPress plugin called Recent Posts Widget that you can see in the sidebar on the home page (not sure where it shows up on a phone). I configured it to randomly display five posts from the Quotable & Notes category. Each time you refresh the page, you see five different quotes. 

I’m quite pleased with this widget because it serves up some of my favorite posts. Pretty sure you can’t do this kind of thing on the social media platforms that only care about the last five minutes.

Blog Queens

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Nikol Lohr, Halley Suitt, and Ana Marie Cox were three of my favorite bloggers during those glorious days before Facebook, Twitter and the social media silos that eventually killed blogging. I asked Claude where are they now:

Nikol Lohr was one of the early voices that helped establish the personal, confessional, and genuinely funny register that defined the best blogging of that era — a woman writing with wit and candor about her actual life, which was rare and influential. She’s hard to find in formal “influence” histories because she wasn’t covering politics or tech, she was just brilliantly herself. She eventually landed in rural Kansas, where she runs The Harveyville Project, a creative retreat housed in a former school. It’s home to Yarn School, Mitten School, Cheese School, and other maker-focused programs.  She’s also become a knitwear designer with a real following — her book Literary Knits featured 30 patterns inspired by favorite works of fiction , which is a very Nikol thing to do. A genuinely successful second act, even if it’s far from the blogging world.

Halley Suitt (now Halley Suitt Tucker) was more embedded in the tech/blogger conference circuit and had real crossover credibility in the business world. She wrote a Harvard Business Review case study on blogging in a work context  — one of the first pieces of that kind — which helped legitimize blogging as a serious phenomenon to people in suits. She was also a senior editor at Worthwhile Magazine and appeared on Oprah.  More recently, she’s described herself as an entrepreneur and TechStars alum, and was doing a podcast called the G3 Girl Geek show  and writing for the Boston Globe’s BetaBoston tech vertical. Her profile seems to have quieted considerably in the last few years — the most recent activity I can find is mid-2010s startup and women-in-tech writing. Her blog Halley’s Comment is still technically up but the last substantive posts are from around 2014.

Ana Marie Cox is the one with the highest-profile trajectory, though it’s taken some sharp turns. She became the founding editor of Wonkette in 2004, covering Capitol Hill politics with irreverence and sharp commentary , which made her a genuine media figure rather than just a blogger. She moved through Time, GQ, Air America, The Guardian, and MTV News. She’s now a political columnist for The New Republic and hosts the sci-fi/political science podcast Space the Nation with Dan Drezner.  She’s also been very public about sobriety and mental health — she ran a “Sober Questioning” column at The Cut through 2022  — and has a memoir about addiction and intergenerational trauma forthcoming from Random House, though it remained unpublished as of 2025.  She’s also launched a writing workshop called The Third Story Workshop focused on processing difficult experiences through narrative.  She left Twitter after Musk took over and is now on Bluesky and Instagram.

All three represent something real about that early blogging moment — women writing with authority, personality, and without institutional permission — which was more radical than it sounds now.​​​​​​​​​​​​​​​​

AI-chats vs. Artificial Intelligence

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Consider this a “house keeping” post to explain some changes to categories and tags. (I let Claude.ai write this one.)

The Artificial Intelligence category is for posts about artificial intelligence as a subject. Additionally, I’ve had a tag (ChatGPT) I used for posts featuring the more interesting conversations with that LLM. Those threads often had nothing to do with AI. Furthermore, I posted a number of conversations with Gemini, Perplexity and Claude.

So I’ve created a new tag (AI-chats) I’ll use for chats with any of the models I’m using these days. And I’ve deleted the ChatGPT tag. If I want to find posts specifically about that particular LLM, I’ll search for “ChatGPT.” (Or Claude or Gemini)

The secondary observation: that corpus (the AI-chats posts), properly tagged, may be among the more historically interesting subsets of the archive. Not because of the AI side — future systems will be unrecognizable — but because it documents how one person thought alongside these early tools, in real time, before the medium found its shape. The tag marks the seam between the solo voice and the dialogic one.

When AI can “read” my blog

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Even the people who seem to understand AI large language models best, don’t pretend to know how capable they will become in the near future. Against that backdrop, can you foresee a time when an AI can scan/analyze the 6,400 posts of my blog (without having to upload the files)? [Full thread]

Claude.ai: Given that you’ve written 6,400 posts, you’ve clearly been at this a long time — that’s a substantial body of thought. Here are the possibilities I find most genuinely compelling:

Intellectual archaeology
Tracing how your thinking has actually evolved over time — not how you remember it evolving. Most prolific writers are surprised when an outside reader identifies the real turning points, the ideas you quietly abandoned, the obsessions that recur in disguise. An AI could map this with precision a human editor never could, simply because of the volume.

Finding your strongest work
Long-form bloggers almost always have brilliant posts buried under the sheer weight of output. An AI could identify which pieces are most original, most internally coherent, or most likely to resonate — not by traffic metrics, but by the quality of the thinking itself. That’s a different and arguably more honest filter.

The book you haven’t written
6,400 posts almost certainly contain one or more books worth of coherent argument that you’ve never assembled into a single form. An AI could identify the connective tissue — the thesis that runs underneath years of posts — and propose a structure you couldn’t see because you were too close to it.

Contradiction and tension mapping
Where have you argued both sides of something over the years? Not as a gotcha, but as a genuine map of your intellectual uncertainty — the questions you keep returning to because you haven’t resolved them. Those unresolved tensions are often where the most interesting thinking lives.

A “second brain” interface
Rather than one-time analysis, an ongoing conversational layer over your entire archive — so you could ask things like “have I written about this before?” or “what’s my actual position on X when I look across everything I’ve written?” Your blog becomes a queryable extension of your own memory.

Your readers’ experience
Surfacing unexpected connections for new readers — showing someone who just found one post, the three other posts from 2014 and 2019 that are in genuine dialogue with it, even though you never linked them.

The thread connecting all of these is that the real value isn’t in the individual posts — it’s in the patterns across all of them that nobody, including you, has ever been able to see all at once.

Continue reading →