0.0 Context Setting

Monday, 17 August in Portland, Oregon. I don’t think I’ve been outside today? I should go outside.

All we want to do is figure out what to do about the fridge/freezer that is now only fridging and not freezing. You’d think it would be a simple decision but ohhhhh no we just had to evolve ourselves a consciousness and mess everything up.

0.1 Events

0.1.1 How People Work... Does Happy Hour!

It’s a new show! A free, 45-minute open weekly clinic where you can come along and I’ll work with you on getting you and your team unstuck.

No idea how many spots are left, but you can register here:

• How People Work... Does Happy Hour! on Tuesday 19 August, at 1pm Pacific.

0.1.2 How People Work...

Here’s the next three How People Work, Live! events:

• How People Work, Live! ... with Marcin Wichary on Friday 21 August 2026

Marcin Wichary, who started his career at Google working on internal tools, the search team, the doodle team, and the HTML advocacy team. He later spent time at Code for America and Medium, and his most recent position has been working as a design director and design architect on the editor team at Figma.

Marcin has also been speaking and writing about craft, typography, and interface design since the early 2010s. In 2024 he published Shift Happens, a book about the history of keyboards and typing, and his most recent endeavour has been a blog about software craft and quality called Unsung.

• How People Work, Live! ... with Margo Stern on Friday 28 August, 2026

Margo Stern, the author of Good Work: Managing Yourself and Managing Managing, a two-sided book that shares all the tips, tricks, hacks and cheat codes to working in tech. Drawing not only on her experience managing and being an IC at places like Google, Twitter, and Lyft, she shares the wisdom from interviews with PMs, Designers and Engineers who have been there too. Margo is also a Staff Content Designer at Lyft, and she lives in San Francisco, CA.

• How People Work, Live! ... with Sarah Vieria on Friday 4 September, 2026

Sarah Vieria is a product leader and founder of Mother Blackbird, where she helps organizations build better products, websites, and systems. She loves crafts, creative problem solving, and the kind of projects that start with “I wonder if I could make that.”

In the meantime, you can follow the show playlist and/or subscribe to the channel (ugh can’t believe I’m actually saying that). If you do subscribe to the channel though that would be great because the kids asked how many subscribers I have (“Uh, I think maybe 45?”) and they were VERY supportive because their next comment was “Out of eight billion people?!” and then I died.

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1.0 Some Things That Caught My Attention

I wanted to do a better job of the first one today, not sure if it made it or it just petered-out. But I wanted to get it out more than get it right, as it were.

1.1 Technology is a tool and we have choices to make as a society

The San Francisco Chronicle published an analysis of how much the city’s workers get paid:

A small group of San Francisco police officers and sheriff’s deputies earn more than most of the city’s executives, with several making more than $800,000 in total compensation a year, largely due to enormous overtime earnings that sometimes tripled their wages.

Of the roughly 700 city workers who made over $450,000 in compensation and worked full-time last year, 72% worked in the police, sheriff or fire departments — even though those agencies account for less than 20% of the city workforce. ¹ (my emphasis)

There’s a lot to say about policing in American cities, not much of it good. But there are a few things going on here that caught my attention. One: police budgets in cities are huge! San Francisco’s 24/25 police budget was $822 million, up 6.18% on the previous year². Call that five percent. The San Francisco Unified SChool District adopted a $1.2 billion total operating budget for the 25/26 school year, to give you some comparison.

Anyway, I’m getting ahead of myself there.

One of the reasons why the SF PD’s budget is so big is apparently because of being under-resourced and needing to pay overtime³:

Indeed, even though overtime increased by 85% between 2019 and 2023, the total number of hours worked by SFPD, including regular shifts, decreased by 6% over the same period, according to city data, which means that all the overtime is still not making up for the lack of full-time staff.

I have two glib comments: if you’re persistently over budget because of needing to pay overtime then clearly you have structural issues somewhere. (I mean, just across the bay, the Oakland PD appears to have serious issues just keeping track of whether anyone’s done any overtime in the first place⁴). I mean, maybe you need to get someone in who can budget better. Maybe you have something more fundamental going on.

I wouldn’t imagine to know what goes on in a police department. I mean, I could imagine. I would be making it up. I am entirely capable of making a guy up to be mad at, so let’s try to do that as responsibly as possible.

Anyway. You’ve got a Sergeant 3 in the SFPD making a total compensation of $872,028. I mean, that’s a pretty senior police officer, I’d hope. Base salary for a teacher in SF USD starts at what, something like $70,000.

I will note that as far as I’m aware, teachers don’t get paid overtime. Maybe they should! There’s a whole conversation about unions there!

Let’s assume that like any other bureaucracy, police departments are inefficient. There’s a bunch of so-called knowledge work. There are record keeping systems. You want record keeping systems! They’re hopefully part of a set of checks and balances, you know, so you can make sure the custard watchers are properly supervised.⁵

This is the kind of thing information technology is supposed to help with, but I think we’re all in broad agreement that what information technology gives in one mousing hand it takes away with the other keyboard hand.

So here’s how the thinking goes.

Do we know how much it costs to do policing? I mean, we kind of do, but also not. What are all the staffing needs? Is it also shoe leather requirements, do people want to see visible policing? Is that a thing?

I would not presume to know all the answers here. The thing is, you could do this if you wanted to. I know there’s a load bearing “just” in the “you could just”. But.

You want safer streets? You could put cameras on them. The problem with cameras is that it’s surveillance, and surveillance generally helps the big guy get what the big guy wants, which is often to keep the little guy down. In America, this is mostly a description of institutional racism. Speed cameras work in most every single other country (citation needed!), but their failure mode in America isn’t just the inherent distrust of institutional authority and government, it’s also that speed cameras are used by in a racist environment where it’s very easy to be racist accidentally (that’s what institutional means!) never mind actually racist.

But, that’s a choice. It’s difficult, not impossible. You could design software and technology and camera surveillance with people in a way that has the best chance of meeting society’s design goals.

Look, here is a stupid one. You can have cameras that don’t record everything. You can have cameras that throw data away. I know there’s a tension in keeping all of that lovely footage -- never know when you might need it -- but then you’re back in the Flock issue of “there are some really bastardy bastards out there and we can’t trust them”. You could make some shit up. You could say, and just stay with me on this:

You could say, hey, so there’s footage on this camera but it’s encrypted so no one can see it. So we need, I don’t know, something like a grand jury to even look. I know, right?! So irritating! But what if (and again, just stay with me), we could do a push-notification on-demand grand jury with relevant members of an appropriate pool (say, residents within n miles of the camera in question), and that the jury request allows access and only access to the specifically sought footage? (Sure, analogue gap and all that. Can’t fix everything, don’t let the perfect be the enemy of the better and the improve-society-somewhat).

You could decide to do that. You could decide to more directly allow communities to not only decide where they want cameras (clearly they all want them, to some extent, on their front doors), but to also decide what they’re used for (clearly, for some people, not to be fucking snitches).

This should have been a consultative process, one that’s more deliberate than “we are buying new cameras to do our policing”. It could have been. If we had more informed and more deliberate governance, if we actually elucidated the needs of a community first and had a way of negotiating them, then maybe what we would get wouldn’t just be whatever a vendor markets.

So instead, you get shit popping up like sparrowmap, a sort of David Brin-sousveilance-esque potentially vibe-assisted app that will take any RTSP stream or phone and, more or less, start counting cop cars. Just like that. Because Flock crossed a line.

(And it’s not just Flock, Flock is in like the front line of war that’s just breaking out and essentially a proxy for tech-enabled-extraction-based-unregulated-capitalism)

The whole point of technology is that it’s supposed to be what you develop as a tool to solve your problem, and we’re just both simultaneously far off that and so close. The story -- thanks to that tech-enabled-extraction-based-unregulated-capitalism -- everywhere instead is surveillance and data and administration. Your schools will watch your kids because they can, your employer will watch you because you can, the data offgassing will be collected and made closed-loop to train more generators.

But the annoying thing, the most fucking annoying thing, the thing that pisses me off is that finally Regular People are starting to be able to use computers to do things, or to make computers to do things, and it’s all built off original sin and blood bytes.

(There is a very brief aside here, I posted somewhere that you can look around and see what people would do in a post-scarcity society because they’re doing it right now. What they’re doing -- people are doing -- is creating. Still. Still drawing, writing, making videos, making films, making music, whether manually or with generative assistance, and especially whether or not they’ll ever get any money for it. It seems like humanity’s slogan isn’t just only connect, but it’s also only create.)

All of this is to say: these are choices and what would it take for us to stop and make a decision.

1.1 It’s magic

Look, I’m worried there’s a high chance this is just going to sound like late-night undergraduate conversation. In my defense, I’m going to say that I’ve been interested in linguistics and cognitive psychology since my teens. Which might make it worse, on reflection.

It’s amazing, magic even, that reading a bunch of words can significantly affect your physiological state. Just the idea that contrasting squiggles on a flat surface, whether through ink or pixels, can make you feel something.

(Not even words! Just air molecules jiggling around!)

Someone distant in time and space can put a thought into your head and all the associated thoughts, and just that thought or thoughts, they can set your heart racing. Give you chills.

I specifically mean reading, here. Visual media doesn’t count, it’s way easier.

Words and symbols. That’s a whole lot of materialism going on there. You’re even getting to the point where a thing-that-is-not-conscious (i.e. an LLM) can generate a string of words (carefully, not “writing”), and that string of words when encountered by a human can then turn into a thought. Did a thought create those words? Arguably not? Does thinking happen when the words are consumed and interpreted? Yes, just through the nature of consumption and interpretation. It is as if you are a thinking machine: you cannot help but take in input and react to it. There is no “don’t think about this”, your body will react to it because your brain is a part of your body and your brain will react to it because how could it not?

Anyway. Magic, I tell you. Magic. Language is what you’d call magic.

1.2 Licking envelopes can be fun

Some of you may have encountered my summer project. I was challenged(?) by Jennifer Anastasoff to go and make a project of talking to two people a day for four weeks (a month) and that by the end of that period, I would have way more thoughts about what I want to be when I grow up (and, honestly, more ideas about what to pitch for/where to pitch, and where to apply).

I have got to tell you, I was not a fan of this homework assignment. Sending out the first few emails or requests was like pulling teeth: Hello! How are you?! I would like to catch up with you and find out what you’re up to!

But then apparently I turned the licking envelopes into a game, and have now ended up getting in touch with sixty-odd people? And have caught up with maybe thirteen people already? My familiar tells me I’ve got another 28 scheduled?

All it took was for me to rejig the entire thing in my head as not an obligation (ugh I have to catch up with 10 people a week) and instead turned it into Dan’s Virtual Summer Catchup Tour. And now I’m just going around wily-nily asking people if they’d like to catch up. And most of them are saying yes?

(In any event, if I have not asked you and you think we should catch up and find out what each of us is doing, then... you should get in touch.)

The best thing about telling people you’re going on a (virtual) summer catchup tour is the “summer” part -- I figured out you can just do it again the next season. And the one after that! Doesn’t even feel weird at that point. Just feels fun.

Anyway, though some people might appreciate the motivation hacker/sideways positioning there. Not an obligation, a FUN TOUR.

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That’s it for today. How are you doing?

Best,

Dan