0.0 Context setting

Sunday, 13 September 2026 in a cold and dreary Portland, Oregon. This one has taken a long time to write! I’ve been feeling increasingly guilty about how long it’s been since the last time, but things have been pretty busy.

0.1 How People Work, Live

Last episode was with Dana Chisnell and we had a great candid chat about small-p politics at work. I especially loved her framing about how soft skills are actually power skills.

Dana’s episode is up on the podcast and YouTube now; you can catch up on anywhere RSS works with your podcast app, Apple Podcasts, Spotify, and YouTube.

(132 subscribers on YouTube now! Tell your friends!)

Next up!

Friday 18 September at 9am PT: How People Work, Live! ... with Anna Pickard

Anna Pickard, a writer who does more talking about writing than writing. She mainly works as a consultant in Voice and Tone, helping companies sound human, and helping writing teams get their work done. After training in theatre, she worked in journalism, advertising and games, before stumbling into tech. From 2014, she was responsible for moulding, evolving and shaping the voice of Slack, and since leaving in 2020, has worked with Apple, Airbnb, Atlassian and a bunch of other companies that don’t begin with A.

After that, on 25th September it’s Michele Tepper who amongst other things co-founded Archive of Our Own and designed mortgage visualization tools at the Consumer Finance Protection Bureau (RIP), then co-founder of 18F Hillary Hartley on 2nd October, and Jim Ray from Bluesky on 9 October. Check out the show page for the whole list.

Meanwhile, there’s the open How People Work... Does Happy Hour open clinic on Tuesdays at 1pm PT, where you get to bring what you’ve been thinking about and we chat about it as a small group.

1.0 Some Things That Caught My Attention

1.1 What does recording even mean?

In the pilot episode of Person of Interest from 2011 there’s this bit of dialogue:

But the Machine? The Machine is everywhere. Watching us with 10,000 eyes. Listening with a million ears.

(You know what, I capitalized the Machine, but I actually have no idea whether it’s capitalized in the script. I feel like that matters.)

So yesterday Apple had their big event where they launched their foldy iPhone (cool, I reckon, but also $2,000 of expensive, and also probably at least 5 years until it ever reaches down to something like $1,000), but also new Apple Watches with, at least in my corner of Bluesky, some Divisive Features.

The Apple Watch Series 12 (and the chonkier, more expensive Ultra 4) have this feature called Live Rewind. Here’s what Apple has to say about it:

Live Rewind catches what you missed. Did someone say something you couldn’t hear in a loud restaurant or share cooking instructions you didn’t quite catch? Just double-click the Digital Crown, and Live Rewind transcribes what was said in the last 15 seconds. You can ask Siri about the content of the transcript or save it to the new Siri app to revisit later.¹

(Some) people are (understandably) upset about this! I don’t think there’s any way around this upset, even with Apple having gone to the lengths of preparing an eleven-page PDF² about how the audio intelligence system that powers Live Rewind deals with privacy.

First, there was a debate on Bluesky about whether what Apple’s doing here is “recording” audio which was incredibly frustrating to me because social media microblogging means there isn’t really context to explain that “recording” can mean very specific things in certain contexts, like in law!

And it’s this collision that is difficult: you fundamentally can’t do any processing without some sense of “recording” because the whole deal of the Turing computer is that you have, say, your infinite tape upon which you “record” data, and then you have instructions that act upon that data. However transient, there must be data for you to be able to process it, all the way through to transient RAM, which people learn as the kind of stuff that disappears when you turn a computer off.

But this is besides the point. There are technological issues here to do with computing and processing and storage, and while those are inextricably linked from social aspects, there are also distinct social aspects that we haven’t really dealt with and at the same time are stupendously thorny.

At issue is this: how ephemeral is speech? When you’re having a conversation with someone, what are the expectations around that speech being recorded, whether the recording is transcription or audio? How long do you expect your words to exist in the world, from day to day? How do those expectations change from context to context, where that context includes both the subject matter, the people you’re conversing with, and more?

People don’t like, I think, in general to be confronted with the exact words they said. When speech is seen to be equivalent with thought (it is, I’d say, the fastest method people have for sharing their thoughts), then what space or grace do you give to someone who is thinking as they’re talking? That’s ultimately the issue here, regardless, unfortunately, of issues like accessibility where live transcription is incredibly useful or critical.

I think people would say that it’s not fair to be judged constantly on your words. For starters, we talk about judging actions, not words. Words are cheap, words can be careless, words can be mere utterances. How long should they stick around? Writing takes effort, perhaps not very much for some people, but I’d argue that writing is also intentional. That’s what’s going on here. The instant that someone’s speech is transformed into another medium -- like text displayed on a screen, or transcribed by a stenographer, or even by someone like me who can type super fast -- then there’s the threat or the fear that it won’t ever go away. ”I didn’t mean that” is a reasonable defence: but then, who else can know whether you meant that or not? The interface between what you think and what you say is known only to the person who made the utterance. The potential for being misunderstood is always there. Transcripts are devoid of context, and I’ve written before that what’s thought of as the technological fix for “not enough context to understand the words as best as possible” is at first glance to gather ever more data, to try to approximate as much context as possible. That’s... not possible. The map, the context you gather, will never be the territory.

”That isn’t what I meant”. I don’t think there is a way around this other than for our behavior and expectations about speech to change. ”He said, she said” is a thing people experience, and it’s one that I think we all find difficult to navigate. People go to court over defamation, whether that’s libel (the written one) or slander (the spoken one).

So I don’t think in that other respect that it matters whether Apple is throwing away the recording, whether that’s the audio or the text, because the mere experience of seeing your words repeated back to you is one that people are afraid of. Part of that fear is down to not knowing what’s going to be done with your words. And there’s that phrase: your words. But when they’re written down, what does your words mean anymore? You don’t have control over them anymore, but they’re still attributed to you. You’re still in a way liable for them. They have the ability to become some sort of permanent record.

There’s a behavior -- a somewhat silly but understandable one, I feel -- where on video platforms like TikTok where the entire experience of what videos you see is decided by a (human-programmed) algorithm people started using euphemisms like unalive for, well, killing or death by suicide. There’s another phenomenon of people attempting to use some sort of visual camouflage to frustrate or disguise themselves from automated machine recognition. I saw a TikTok the other day of someone showing how you can treat a vehicle license/registration plate so that it can be visible to a human but not, apparently, to a camera system like Flock. (You can imagine how popular that video was, you can imagine the sort of comments that were the highest rated).

Language evolves, too. People come up with codes, with euphemisms, to elide meaning. Strategies to ensure that conversations between people remain private, you know, the ones like the merchandise is ready has become such a trope that it practically invites investigation.

Microphones will get smaller. The physical package for processing required to transcribe or record gets smaller. Apple’s latest watches appear to also require an accompany new-enough iPhone to be able to do live rewind, but it’s probably just a matter of time before the transcription can be done solely on a watch.

You don’t know what is going to record you and you don’t know where you’re going to get recorded. You will not know what objects are paying attention to and what objects are not paying attention to you. There don’t need to be people in the room. You will not know who has access to that text. You will know that if it exists, that text could go anywhere, to anyone, and may easily outlive you, even if there’s no present reason to. The cost of there being a permanent record of what you say becomes more and more trivial, and it’s not so much the value in terms of surveillance, but the value in terms of what it could be worth in terms of advertising... but then also it can be stored in case someone wants to buy it in the future.

... and this was all assuming perfect transcription, too.

But then, what’s the alternative? Some sort of legal/regulatory regime where such recording is illegal? Where express consent is required for any such transcription or recording to take place? Those regimes exist already, but then the issue is as it has always been: what does enforcement look like? Who gets to exercise that enforcement? Now we’re back to who has power, and the power differentials that exist in our societies. Who gets to say that no recording happens? Who has that privilege? When is that imbalance recognized? These conversations are recorded for training purposes, but can I record them for consumer rights purposes? Why are consumer rights needed to justify someone recording a conversation? It’s not even clear in some jurisdictions whether you’re allowed to record the actions or speech of a public servant -- police, just so I’m clear -- and even if you’re allowed to record the actions or speech of a public servant, are they going to stop you in practice? Do they in practice exercise the use of force? In which case, what’s a remedy, that the microphones are woven into your clothes, that they’re hidden, that you don’t need to hold a phone up in the first place?

1.2 Do it stupid first

I have been stressing out for months about how I “should” be making clips and vertical video to market the workshop series and, to be honest, what it is I do in the first place. Most of the work I get as a consultant is through referral. Ultimately that means a mix of people who have worked with me before and know people who would benefit from working with me, and in the other case people who have read this newsletter and have an idea how I think and operate, and are willing and interested enough to see if what they see I do and how I work can help them with their problem.

The problem, such as it is, is that apparently people don’t read and you “should” make vertical video and just because my TikTok/Reels/LinkedIn video is not full of, I don’t know strategytok doesn’t mean it doesn’t exist and, in its own way, can be influential.

But like I’ve noticed with many other things in my life, I get hung up on how to do things properly. Some of this I think has been trained into me: as a baby lawyer, you certainly get trained into writing client advice properly, and writing You’ll Be Hearing From Our Lawyer letters properly. Which as I practice and teach is all about knowing your audience (including what they need) and being clear about what it is you need to communicate and happen.

But see the issue is getting hung up on “doing a vertical video properly” which in my head is a bit like this:

• going through existing shows
• finding relevant clips
• editing them
• framing them
• figuring out how to top/tail them
• figuring out what sort of captions to do

Like, I’d have to learn how to do all that stuff which is fine but by the time I’ve gotten those bullet points I’m also thinking about form, and I recently realized that dealing with the form stuff is bullshit. It’s a chore, and the kind of chore that I can also notice I’m spending mental energy in avoiding doing. It’s genuinely making me stressed out!

The solution to this is to do what I was told to do when I was commissioned to write a print piece for the first time: that I’d been commissioned precisely because of how I write and how I would tell the story, and not solely because I had experience of the subject matter. I got so stuck on writing it “the proper way” for a print magazine that I rather unhelpfully started blowing past deadlines until I was told in no uncertain (and I must be absolutely clear, incredibly supportive, compassionate, and sympathetic) terms that writing the way I would write it was what was needed. (The other lesson I learned was that an editor’s job is to take your writing and make it better, and not to be like an essay assignment where you get things wrong. You can even choose not to accept edits!)

So the insight here is to not try to do a vertical video and instead do it stupid and have fun, and practice that way. And kind of intentionally try not to mimic any sort of style or anything like that. Well. We’ll see if thinking about things that way helps.

That’s it for this episode. I love getting replies and notes from people, and reply to all of them (eventually, at least). How have you been doing?

Best,

Dan