AI is everywhere, but most websites are still managed manually by humans using content management systems like WordPress and Drupal. These systems provide means for tagging and categorizing content. But over time, these structures degrade. Without vigilance and maintenance, taxonomies become less useful and relevant over time. Users struggle to find stuff. Ambiguity creeps in. Search results become incomplete and unreliable. And as terms proliferate, the team struggles to maintain the site, making things worse. The site stops working as well as it could. Sales, engagement, and trust suffer. And the problem only gets worse over time. Eventually, the team embarks on a redesign. But hitting the reset button only fixes things for a while. Entropy is the nature of things. Systems tend toward disorder unless we invest in keeping them organized. But it’s hard: small teams have other priorities. They’re under pressure to publish quickly. Turnover is high. Not ideal conditions for consistent tagging. Many content teams don’t have governance processes for taxonomies. Folks create new terms on the fly, often without checking whether similar ones exist. But even when teams have the structures and processes needed to do it right, content and taxonomies themselves change over time as the org’s needs and contexts evolve. The result is taxonomy drift, the gradual misalignment of the system’s structures and content. It’s a classic “boiled frog” situation: since it happens slowly, teams don’t usually recognize it until symptoms emerge. By then, the problem is harder and more expensive to fix. Avoiding taxonomy drift calls for constant attention and manual tweaking, which can be overwhelming for resource-strapped teams. But there’s good news on the horizon: this is exactly the kind of gradual, large-scale, boring challenge where AIs can shine. I’ve worked on IA redesigns for content-heavy websites and have seen the effects of taxonomy drift firsthand. Often, one person is responsible for keeping the website organized, and they’re overwhelmed. After a redesign, they face three challenges: Implementing the new taxonomy on the older corpus. Learning to use the new taxonomy in their workflows. Adapting and evolving the taxonomy so it remains useful and consistent over time. AI is well-suited to tackling these challenges. LLMs excel at pattern matching and categorizing existing text at scale. Unlike humans, AIs don’t get overwhelmed or bored when categorizing thousands of items over and over again. And with predefined taxonomies, they’re not as prone to hallucinations. I’ve been experimenting with using AI to solve taxonomy drift, and the results are promising. I’m building a product to tackle this issue, and looking implement the approach in real-world scenarios. If you or someone you know is struggling to keep a content-heavy website organized, please get in touch.

Episode 5 of the Traction Heroes podcast featured a conversation about strategic priorities. What do I mean by that? I’m referring to prioritizing at two levels: When you’re thinking about what to focus on now – what you should and shouldn’t do next. When you’re thinking about the higher-level objectives those granular actions serve. What use is it to be productive or efficient if it’s moving you in the wrong direction? Or as designers put it: there’s a difference between designing the right thing and designing the thing right. Of course you want to do things right. But first, you want to ensure the thing you’re doing is worthwhile to begin with. Both levels of priorities matter. As you may expect, this is straight up Harry’s alley, as it’s central to Managing Priorities. I was glad to have this conversation with him – especially since it was prompted by a passage from a book he found through me! I hope you find this conversation valuable. As always, I’d love to know what you think. (And if you’re enjoying the show, please leave us a rating – it helps other folks find us.)

Week 10 of the humanities crash course had me reading (and listening to) classic Greek plays. I also listened to the blues and watched a movie starring a venerable recently departed actor. How do they connect? Perhaps they don’t. Let’s find out. Readings The plan for this week included six classic Greek tragedies and one comedy: Sophocles’s Oedipus Rex, Oedipus at Colonus, and Antigone, Aeschylus’s Agamemnon, Euripides’s The Bacchae, and Aristophanes’s Lysistrata. The tragedies by Sophocles form a trilogy. Oedipus Rex is by far the most famous: the titular character discovers he’s not just responsible for his father’s death, but inadvertently married his widowed mother in its wake. Much sadness ensues. The other two plays continue the story. Oedipus at Colonus has him and his daughters seeking protection in a foreign land as his sons duke it out over his throne. In Antigone, Oedipus’s daughter faces the consequences of burying her brother after his demise in that struggle. In both plays, sadness ensues. Agamemnon dramatizes a story we’ve already encountered in the Odyssey: the titular king returns home only to be betrayed and murdered by his wife and her lover. The motive? The usual: revenge, lust, power. Sadness ensues. The Bacchae centers on the cult of the demigod Dionysus. He comes to Thebes to avenge a slanderous rumor and spread his own cult. Not recognizing him, King Pentheus arrests him and persecutes his followers, a group of women that includes Pentheus’s mother, Agave. In ecstatic frenzy, Agave and the women tear him apart. Again, not light fare. Lysistrata, a comedy, was a respite. Looking to end to the Peloponnesian War, a group of women led by the titular character convince Greek women to go on a sex strike until the men stop the fighting. For such an old play, it’s surprisingly funny. (More on this below.) These plays are very famous, but I’d never read them. This time, I heard dramatizations of Sophocles’s plays and an audiobook of The Bacchae, and read ebooks of the remaining two. The dramatizations were the most powerful and understandable, but reading Lysistrata helped me appreciate the puns. Audiovisual Music: Gioia recommended classic blues tunes. I listened to Apple Music collections for Blind Lemon Jefferson and Blind Willie Johnson. I also revisited an album of blues music compiled for Martin Scorcese’s film series, The Blues. My favorite track here is Lead Belly’s C.C. Rider, a song that’s lived rent free in my brain the last several days: Art: Gioia recommended looking at Greek pottery. I studied some of this in college and didn’t spend much time looking again. Cinema: rather than something related to the readings, I sought out a movie starring Gene Hackman, who died a couple of weeks ago. I opted for Francis Ford Coppola’s THE CONVERSATION, which is about the ethics of privacy-invading technologies. Even though the movie is fifty-one years old, that description should make it clear that it’s highly relevant today. Reflections I was surprised by the freshness of the plays. Yes, most namechecks are meaningless without notes. (That’s an advantage books have over audiobooks.) But the stories deal with timeless themes: truth-seeking, repression, free will vs. predestination, the influence of religious belief on our actions, relations between the sexes, etc. Unsurprisingly, some of these themes are also central to THE CONVERSATION. I sensed parallels between Oedipus and the film’s protagonist, Harry Caul. ChatGPT provided useful insights. (Spoilers here for both the play and movie – but c’mon, these are old works!) Both characters investigate the truth only to find painful revelations about themselves. Both believe that gaining knowledge will help them control events – but their efforts only lead to self-destruction. Both misunderstand key pieces of evidence. Both end up “isolated, ruined by their own knowledge, and stripped of their former identity.” (I liked how ChatGPT phrased this!) Both stories explore the limits of perception: it’s possible to see (and record) and remain ignorant of the truth. Heavy stuff – as is wont in drama. Bur for me, the bigger surprise in exploring these works was Lysistrata. Humor is highly contextual: even contemporary stuff doesn’t play well across cultures. But this ancient Greek play is filled with randy situations and double entendres that are still funny. Much rides on the translation. The edition I read was translated by Jack Lindsay, and I marveled at his skills. It must’ve been challenging to get the rhymes and puns in and still make the story work. A note in the text mentioned that the Spartans in the story were translated to sound like Scots to make them relatable to the intended English audience. (!) Obviously, none of these ancient texts I’ve been reading were written in English. That will change in the latter stages of the course. I’m wondering if I should read texts originally written in Spanish and Italian in those languages, since I can. (But what would that do to my notes and running interactions with the LLMs? It’s an opportunity to explore…) Notes on Note-taking Part of why I’m undertaking this course is to experiment with note-taking and LLMs. This week, I tried a few new things. First, before reading each play, I read through its synopsis in Wikipedia. This helped me understand the narrative thread and themes and generally get oriented in unfamiliar terrain. Second, I tried a new cadence for capturing notes. These are short plays; I read one per day. (Except The Bacchae, which I read over two days.) During my early morning journaling sessions, I wrote down a synopsis of the play I’d read the previous day. Then, I asked GPT-4o for comments on the synopsis. The LLM invariably pointed out important things I’d missed. The point wasn’t making more complete notes, but helping me understand and remember better by writing down my fresh memories and reviewing them through a “third party.” I was forced to be clear and complete, since I knew I’d be asking for feedback. Third, I added new sections to my notes for each work. After the synopsis, I asked GPT-4o for an outline explaining why the work is considered important. I read these outlines and reflected on them. Then, I asked for criticisms, both modern and contemporary, that could be leveled against these works. Frankly, this is risky. One of my guidelines has been to stick to prompts where I can verify the LLM’s output. If I ask for a summary of a work I’ve just read, I’ll have a better shot at knowing whether the LLM is hallucinating. But in this case, I’m asking for stuff that I won’t be able to validate. Still, I’m not using these prompts to generate authoritative texts. Instead, the answers help me consider the work from different perspectives. The LLM helps me step outside my experience – and that’s one of the reasons for studying the humanities. Up Next Gioia scheduled Marcus Aurelius and Epictetus for week 11. I’ve read Meditations twice and loved it, and will revisit it now more systemically. But since I’m already familiar with this work, I’ll also spend more time with the Bible – the Book of Job, in particular. In addition to Job itself, I plan to read Mark Larrimore’s The Book of Job: A Biography, which explores its background. It’ll be the first time in the course that I read a work about a work. (As you may surmise, I’m keen on Job.) This will also be the first physical book I read in the course. Otherwise, I’m sticking with Gioia’s recommendations. Check out his post for the full syllabus. Again, there’s a YouTube playlist for the videos I’m sharing here. I’m also sharing these posts via Substack if you’d like to subscribe and comment. See you next week!

This weekend, a small team in Latvia won an Oscar for a film they made using free software. That’s not just cool — it’s a sign of what’s coming. Sunday night was family movie night in my home. We picked a recent movie, FLOW. I’d heard good things about it and thought we’d enjoy it. What we didn’t know was that as we watched, the film won this year’s Academy Award as best animated feature. Afterwards, I saw this post from the movie’s director, Gints Zilbalodis: We established Dream Well Studio in Latvia for Flow. This room is the whole studio. Usually about 4-5 people were working at the same time including me. I was quite anxious about being in charge of a team, never having worked in any other studios before, but it worked out. pic.twitter.com/g39D6YxVWa — Gints Zilbalodis (@gintszilbalodis) January 26, 2025 Let that sink in: 4-5 people in a small room in Latvia led by a relatively inexperienced director used free software to make a movie that as of February 2025 had earned $20m and won an Oscar. I know it’s a bit more involved than that, but still – quite an accomplishment! But not unique. Billie Eilish and her brother Phineas produced her Grammy-winning debut album When We All Fall Asleep, Where Do We Go? in their home studio. And it’s not just cultural works such as movies and albums: small teams have built hugely successful products such as WhatsApp and Instagram. As computers and software get cheaper and more powerful, people can do more with less. And “more” here doesn’t mean just a bit better (pardon the pun) – it means among the world’s best. And as services and products continue migrating from the world of atoms to the world of bits, creators’ scope of action grows. This trend isn’t new. But with AI in the mix, things are about to go into overdrive. Zilbalodis and his collaborators could produce their film because someone else built Blender; they worked within its capabilities and constraints. But what if their vision exceeded what the software can do? Just a few years ago, the question likely wouldn’t even come up. Developing software calls for different abilities. Until recently, a small team had to choose: either make the movie or build the tools. AI changes that, since it enables small teams to “hire” virtual software developers. Of course, this principle extends beyond movies: anything that can be represented symbolically is in scope. And it’s not just creative abilities, such as writing, playing music, or drawing, but also more other business functions such as scheduling, legal consultations, financial transactions, etc. We’re not there yet. But if trends hold, we’ll soon see agent-driven systems do for other kinds of businesses what Blender did for Dream Well Studio. Have you dreamed of making a niche digital product to scratch an itch? That’s possible now. Soon, you’ll be able to build a business around it quickly, easily, and without needing lots of other humans in the mix. Many people have lost their jobs over the last three years. Those jobs likely won’t be replaced with AIs soon. But job markets aren’t on track to stability. If anything, they’re getting weirder. While it’s early days, AI promises some degree of resiliency. For people with entrepreneurial drive, it’s an exciting time: we can take ideas from vision to execution faster, cheaper, and at greater scale than ever. For others, it’ll be unsettling – or outright scary. We’re about to see a major shift in who can create, innovate, and compete in the market. The next big thing might not come from a giant company, but from a small team – or even an individual – using AI-powered tools. I expect an entrepreneurial surge driven by necessity and opportunity. How will you adapt?