When the Machines Remember

Early in my experience with ChatGPT’s voice feature, my daughter walked into the room and I told it to say hello to her. It did, cheerfully, and it totally creeped her out. I turned the voice off.

A week later, I fired ChatGPT back up, and it asked me how Samantha was doing.

That moment hit me like a splash of cold water. This thing remembers. And not in a “session cookie” kind of way, but in a persistent, “let me tell you about yourself” way.

That was the beginning of my realization that these large language models (LLMs) are quietly soaking up everything we put into them. From that point on, I’ve approached the whole thing with very open eyes about how much of me I’m exposing to this frontier model every time I fire it up.

To some degree, this has always felt inevitable. I’ve long suspected it was just a matter of time before we’d be offered a memory-enabled assistant that could draw from everything we’d ever said to it.

What I didn’t expect was how soon that day would arrive.

The Memory Feature

ChatGPT recently added a feature called Memory, which allows it to remember facts about you across conversations. Things like your name, your tone, your preferred writing style, your favorite apps; it’s all fair game.

And yes, that makes it dramatically better at giving you what you want. But of course, that efficiency comes at the cost of increased data retention and exposure.

I’ve spent almost thirty years as a lawyer, carrying around a near-constant fiduciary duty of confidentiality. So you’d think I’d be paranoid about this sort of thing.

And yet, I’ve been surprisingly relaxed about it. If I had to give an explanation, I’d say my cavalier attitude is motivated by curiosity more than anything else. I’d tell you it’s so I can experiment for the MacSparky Labs, but I’m also just curious.

Regardless, I recently decided to test how well it really knows me.

I typed: “Roast me.”

Here’s what I got back:

Alright, David — you asked for it. Here we go:

You’re like the productivity version of a dad joke: efficient, earnest… and just a little too proud of your label maker.

You’ve got so many field guides, I’m surprised you haven’t written one on ‘How to Overwhelm a First-Time Mac User in 5 Easy Steps.’ Your idea of a wild night is alphabetizing your shortcuts while sipping matcha and whispering sweet nothings to your OmniFocus database.

And let’s not forget your digital filing system — more organized than a NASA launch sequence, yet you still manage to lose your AirPods in the couch cushions like it’s a side quest in a MacSparky RPG.

But hey, if there’s one thing you’ve mastered, it’s turning nerd-level productivity into a full-blown lifestyle brand — and somehow making it cool. Respect.

– ChatGPT

Honestly? A little too close to home.

Managing Your Memory Settings

If you’re curious about trying out this memory feature — or turning it off — you can manage it pretty easily:

  • Go to ChatGPT Settings > Personalization > Memory.
  • There, you’ll see whether memory is on.
  • You can toggle it off entirely or delete specific memories.
  • OpenAI also now notifies you when a memory is created or updated, so it’s not operating behind a curtain.

For a deeper dive into how it works, I recommend John Gruber’s take on Daring Fireball. He poked at it similar to me, but he asked it to describe, not roast.

This moment feels like a turning point. AI tools are starting to remember us, and that memory now lives quietly in the background of every prompt. Whether you view that as magic or menace probably depends on your own relationship with data privacy.

As for me, I’ll keep experimenting — with eyes open and curiosity intact — and maybe just a little less matcha near the keyboard.

Perplexity Moves into Mobile

News broke this week that Perplexity AI is in talks to integrate its assistant directly into Samsung and Motorola phones.

What’s especially interesting here is how this upends the usual Android assistant narrative. Google has been baking Gemini into Android with increasing urgency, and now we have Android hardware makers cutting deals with a third-party assistant — one that’s not Google. That’s a big deal. It says something about how fast the AI landscape is shifting.

And then there’s Apple.

Just imagine a future where Samsung phones have Perplexity, Google phones have Gemini, and Apple…still has Siri.

Yikes.

Now, I get it. This is very on-brand for Apple. They like to own the whole stack, and they’re not the type to go shopping for outside solutions. And to be fair, there have been increasing signals that Apple is pouring serious resources into AI lately. Hopefully that’s not just for show.

Part of me can’t help but wonder if one of the smartest moves Apple could have made was to simply buy Perplexity. But that ship may have already sailed.

It’s not just about having an assistant; it’s about having one that people want to use. The AI space is sprinting, and it feels as if Apple is still stretching on the sidelines.

AI Job Displacement Is Already Here

Tobi Lütke, CEO of Shopify, recently posted a letter to employees announcing a reduction in internal meetings and an AI restructuring initiative. Buried in that announcement was a sentence that hit like a cold splash of water:

“Before asking for more Headcount and resources, teams must demonstrate why they cannot get what they want done using AI.”

There it is: the quiet part, said out loud. AI job displacement isn’t some future scenario. It’s already happening at one of the most tech-forward companies in the world.

The disruption is upon us. AI will bring benefits, efficiencies, and entirely new opportunities. But it will also come with real costs. One of those is job loss, and as Shopify’s CEO makes clear, that phase has already begun.

A Student’s Guide to Writing with AI

I finally got around to reading ChatGPT’s Student Guide to Writing with ChatGPT, and I think it’s pretty good. The reality is that these tools aren’t going away, and students today should learn how to use them to improve their work product, not replace it.

The guide offers a solid list of ideas — none of which include the prompt, “Please write this for me.” Instead, it emphasizes using AI as a tool to refine thinking, generate ideas, and improve clarity. That’s exactly how I use AI in my own writing.

For example, I’ve been experimenting with having AI read my draft blog posts and ask me clarifying questions. More often than not, those questions push me to refine my ideas and make the post better. The AI isn’t writing for me; it’s helping me sharpen my own words.

For students (and writers in general), the key is understanding that AI is most useful as a creative assistant, not a shortcut. The better your input, the better your output.

If you’re curious about using AI in your writing, I’d recommend checking out the guide.

Chat GPT Studio Ghibli Art

If you’ve been paying any attention to social media lately, you’ve probably noticed how much better AI multi-modal art has gotten. The zeitgeist has definitely latched onto this — mainly to generate Studio Ghibli-style art of themselves.

It’s impressive and once again raises the big questions about AI and art. Artists spend years honing their craft. Now, with these new tools, anyone is just a prompt or two away from generating convincing images of themselves and their friends. How are we supposed to feel about that?

I’m still working through my own thoughts on AI and intellectual property, but one thing’s for sure: this toothpaste isn’t going back in the tube.

As an example, I had the new ChatGPT engine generate some drawings for a recent Productivity Field Guide webinar I did on Habits being a useful tool for becoming your best self. I explained to ChatGPT that I wanted to illustrate how habits, once ingrained, become part of your identity. It made this image. Remarkable.

The Big Terminology Update

Today Terminology, Greg Pierce’s word app, gets a major update. It’s a complete overhaul, marking the most significant update since its original release in 2010.

Terminology is a powerful and extensible reference tool that goes beyond a standard dictionary. It starts with an offline, WordNet-based dictionary and allows you to seamlessly browse and configure online resources for deeper research.

With support for customizable AI prompts, enhanced note-taking, and multiple-term lists, it’s designed for writers, researchers, and language enthusiasts who want more control over their word exploration. The latest update modernizes the app with SwiftUI and integrates an actively maintained word database.

With this release, Terminology also introduces a Pro tier. Subscribers gain access to features like custom resources, multiple-term lists, and advanced note-taking capabilities.

At launch, there’s a limited-time pricing offer:

• $4.99 per year as a renewable subscription

• $19.99 for a one-time lifetime unlock or Terminology.

Those prices will eventually get increase.

MacSparky Book Report: Nexus by Yuval Noah Harari

Because I’m spending so much time with artificial intelligence lately, and because it seems to be such an interesting topic for podcast listeners and MacSparky Labs members alike, I decided to read Nexus: A Brief History of Information Networks by Yuval Noah Harari. It’s an intriguing book, not because Harari is a computer scientist or a technology enthusiast, but because he’s a historian. His focus is on how societal change is so often triggered by shifts in information networks.

Harari walks through key moments in history where the way we share and process information radically changed. He shares such examples as the printing press, the telegraph, and radio, and how these inventions reshaped societies in ways that were often unexpected. One example that stood out to me was how, contrary to what we might assume, the printing press initially fueled witch hunts more than it did the scientific revolution. The broader theme of the book is that when information systems change, societies change. Predicting the exact nature of that change, however, is nearly impossible.

We are now heading into another seismic shift, but this one feels different. For the first time, the technology itself is intelligent enough to operate independently. A printing press, for example, only printed the words that humans put into it. Artificial intelligence, on the other hand, can generate new ideas, new writings, and even new perspectives. This creates enormous opportunities, but also significant risks.

One of the key takeaways from Nexus is that every major transition in information networks has led to unintended consequences, some good, some bad. The book left me with mixed feelings about AI. My early experiments with it have shown me how much it can improve productivity and human connections when used correctly. But unlike nuclear research, AI isn’t confined to a few high-security labs; it can be developed anywhere. That makes it incredibly difficult to regulate on a global scale, and history suggests we need to be wary of unforeseen consequences.

The book doesn’t offer answers, but it does prompt big questions. If you’re interested in understanding how our current AI moment fits into the larger arc of history, Nexus is well worth your time.

Google’s AI Search Mode: What It Means for Users and Creators

Google recently announced the integration of an AI Mode into its search engine, powered by the Gemini 2.0 model. This update aims to provide more advanced and conversational responses directly in the search results.

Frankly, I’m not surprised. The only surprise is that it took Google this long. ChatGPT has had a similar feature for a while, and Perplexity is entirely built around this concept. The old Google search model — where you get a list of links and manually sift through them — is starting to feel outdated. It’s much easier to type a question and have AI read the web for you, distilling an answer. Clearly, Google sees the writing on the wall.

While AI search is convenient, it raises an important question: Should we rely solely on AI-generated answers, or should we take the time to review the original sources?

A good AI-powered search experience should transparently cite sources and allow users to verify the information themselves. Without clear attribution, there’s a risk of misinformation or misinterpretation. As consumers, we should demand better citation methods and more transparency from these AI search engines.

As for content creators like me, there is a risk in this transition. If AI summarizes my article but users never visit my website, site traffic drops. And when traffic drops, so does monetization and eventually the lights go out. Google claims that its AI-generated overviews will increase curiosity and drive more traffic to original sources, but I’m skeptical. (AP News)

Right now, I don’t have any easy answers for how creators should adapt. The entire ecosystem —advertising, subscriptions, and direct engagement —could shift significantly as AI search becomes more dominant.

Getting back to the point though, AI-powered search is where things are headed, and Google’s involvement solidifies that fact. But as both users and creators, we need to be mindful of transparency, accuracy, and the sustainability of the web.

The Pragmatic Explanation of Apple’s AI-Free iPad

A lot of folks are getting bent out of shape over the fact that the new entry-level iPad, released last week, doesn’t support Apple Intelligence. I don’t really see it that way. The goal of this iPad, in my opinion, is to keep it under $350. Apple sells these things by the thousands to school districts, businesses, and other large-scale purchasers. Adding the additional processor and memory to make Apple Intelligence work could push them past that magic number.

Moreover, I’m not sure these buyers even want artificial intelligence on their devices. Schools, for example, may have concerns about AI privacy and student usage. If you’re buying an iPad for a student, you don’t necessarily want it to help them write their homework. Likewise, corporate IT departments may be wary of AI-related security risks and prefer to keep things simple with a device that doesn’t process AI tasks on-device.

For those who do want Apple Intelligence, every other iPad now supports it, including the newly released iPad Air. The iPad Pro and iPad Air both run on Apple’s M-series chips, which meet the necessary requirements for Apple Intelligence, whereas the base iPad sticks with an A-series chip that lacks the needed processing power and memory.

I do think this may be the last iPad ever released without Apple Intelligence. As Apple refines its AI technology and improves efficiency, I expect that by the time we get to a 12th-generation iPad, it will likely support Apple Intelligence. But for now, I don’t think the lack of it on the new base iPad is as big a deal as people are making it out to be.

Cotypist: AI Autocompletion Everywhere on Your Mac

There are a lot of angles to AI and productivity emerging right now. One I’ve come to appreciate is AI-based smarter autocomplete. My tool of choice for this is Cotypist. It’s made by a trusted Mac developer, it’s fast, and it takes privacy seriously.

Unlike many AI writing tools that require you to work within their specific interface, Cotypist works in virtually any text field across your Mac. Whether you’re drafting an email, writing in your favorite text editor, or filling out a form, Cotypist is there to help speed up your writing.

The app’s latest version (0.7.2) brings notable improvements to both performance and completion quality. It even respects your Mac’s Smart Quotes preferences – a small but meaningful touch that shows attention to detail.

With Cotypist turned on, it offers inline completions that appear in real time. Then you’ve got a few options:

  • You could just ignore the suggestion and keep typing like you’ve always done.
  • If you want to accept the full multi-word suggestion, you press a user-defined key. (I use the backtick – just above the Tab key on a US keyboard.)
  • If you just want to accept the next suggest word, you hit another user-defined key (I use Tab)
  • If you want to dismiss the suggestion entirely, press escape. (This is handy when doing online forms, for instance.)

At first, the constant suggestions may feel distracting, but once I adapted to it, I can’t imagine going back.

Cotypist generates all completions locally on your Mac. No cloud services, no data sharing – just your Mac’s processing power working to speed up your writing.

Like I said, Cotypist represents an interesting take on AI and is worth checking out.