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Announcing the Upstream podcast

Open is 1️⃣ all over and 2️⃣ really interesting and yet 3️⃣ there’s not enough media that takes it seriously as a cultural phenomenon, growing out of software but now going well beyond that.

And so, announcement: I’m trying to fill that hole a little bit myself. Tidelift’s new Upstream podcast, which I’m hosting, will:

  1. Pull from across open, not just from software. That’s not because software is bad or uninteresting, but because it’s the best-covered and best-networked of the many opens. So I hope to help create some bridges with the podcast. Tech will definitely come up—but it’ll be in service to the people and communities building things.
  2. Bring interesting people together. I like interview-style podcasts with guests who have related but distinct interests—and the magic is their interaction. So that’s what we’ll be aiming for here. Personal goal: two guests who find each other so interesting that they schedule coffee after the recording. Happened once so far!
  3. Be, ultimately, optimistic. It’s very easy, especially for experienced open folks, to get cynical or burnt out. I hope that this podcast can talk frankly about those challenges—but also be a recharge for those who’ve forgotten why open can be so full of hope and joy for the future.

So far I’ve recorded on:

  • The near past (crypto?) and near future (machine learning?) of open, with Molly White of Web 3 Is Going Great and Stefano Maffuli of the Open Source Initiative. Get it here! (Transcripts coming soon…)
  • The joy of open. At Tidelift, we often focus on the frustrating parts of open, like maintainer burnout, so I wanted to refresh with a talk about how open can be fun. Guests are Annie Rauwerda of the amazing Depths of Wikipedia, and Sumana Harihareswara—who among many other things, has performed plays and done standup about open software. Will release this tomorrow!
  • The impact of open on engineering culture, particularly at the intersection of our massively complex technology stacks, our tools, and our people. But we are often so focused on how culture impacts tech (the other way around) that we overlook this. I brought on Kellan Elliot-McCrea of Flickr, Etsy, and Adobe, and Adam Jacob of Chef and the forthcoming System Initiative to talk about those challenges—and opportunities.
  • The relationship of open to climate and disasters. To talk about how open intersects with some of the most pressing challenges of our time, I talked with Monica Granados, who works on climate at Creative Commons, and Heather Leson, who does digital innovation — including open — at the IFRC’s Solferino Academy. I learned a ton from this one—so excited to share it out in a few weeks.

Future episodes are still in the works, but some topics I’m hoping to cover include:

  • open and regulation: what is happening in Brussels and DC, anyway? Think of this as a follow-up to Tidelift’s posts on the Cyber Resilience Act.
  • open and water: how does open’s thinking on the commons help us think about water, and vice-versa?
  • open and ethics: if we’re not technolibertarians, what are we anyway?

I’m very open to suggestions! Let me know if there’s anyone interesting I should be talking to, or topics you want to learn more about.

We’ll be announcing future episodes through the normal Places Where You Get Your Podcasts and the Tidelift website.

Notes on using Freedom to block digital distractions

Escape” by Metaphox is licensed under CC BY 2.0, via openverse.

I’ve been using freedom.to more or less since it launched. I was recently asked by someone how I use it, and since it didn’t fit in the text box on that platform, here’s a mid-ish-long set of notes on how I use it.

  • Everywhere: It’s on all my devices, no exceptions—iPad, phone, desktop work computer.
  • Scheduled sessions: I use what Freedom calls “sessions” to schedule blocks of time that block out distracting sites. My current blocked sessions are:
    • Working hours: Mostly self-explanatory, starts an hour after school drop-off so I can do some messing around or necessary social stuff before work. Also includes a lunch break every day (actually implemented as two sessions), though unfortunately that isn’t synced to my calendar so sometimes I am unblocked while working and then blocked during my actual lunch.
    • Morning self-care block: There’s an hour in the morning (before family breakfast) that blocks social plus work stuff. Ideal (not always respected) is that I should be using this time mostly for fitness or meditation, not the device. Am sorely tempted to replace this with just keeping the device well away (probably upstairs) and using an Apple TV device for fitness/meditation.
    • Evening family block: From roughly when my son gets home to his bedtime, blocks primarily social. Can still do some work if sorely needed but try to avoid social during that time.
  • Add sites freely: If I’m at all tempted by a site, I add it to the Blocklist. Better to overblock than underblock. (I understand why it probably can’t, but it’d be neat if Freedom monitored web usage, said “I notice that you’ve visited this more than X times today, would you like to block it?” Bonus for: “and add its RSS feed to your feed reader?”) In particular, I mass block sports, social, and news sites—you simply don’t need those things most of the time.

Because of my recent participation in the Mind Over Tech Accelerator trainings (which I cannot endorse enough if you struggle with digital focus!), I’ve made some recent experimental changes to my freedom use. I’m not sure yet if these will stick long-term:

  • Breakfast-time session: I’m experimenting with blocking more things during my family breakfast (6:50-7:50) and just relying on voice control or a shared family kitchen iPad for the few things I need to do during that block. In other words, using Freedom to force me not to touch my own devices during this block of family time.
  • Pomodoro: I’ve been experimenting with Forest for pomodoro timing, but I do wonder if I can do Freedom instead.
  • Apps: Freedom just added the ability to block apps, so I don’t use this yet. Not sure if I will, because most of the things that suck my time can be dealt with by blocking their network connections.

My challenges with Freedom (suggestions welcome!):

  • Reliability: Because Freedom is inherently doing something that the operating system doesn’t love (interfering with your use of the device!) it sometimes stops working, and you have to re-engage it. Which is fine, unless… I’m doing something that it wants to block. For example, during a recent trip, it disengaged and it was more convenient for various reasons not to turn it back on. Which was fine except now I’m back home, I should turn it back on, and I’m… not. (I’ll do it right after I post this! Probably!)
  • Social: My work does sometimes genuinely require use of social, which is hard if you’ve… blocked all social with Freedom. I don’t have a great solution to this, but people are mostly reasonable if you say “actually, I have social blocked on this machine, is it OK if [I do it later, you screenshot it, etc.]”
  • Location: This is a very First World Problem, but when I travel to another timezone, Freedom assumes I’m trying to cheat (not unreasonable!) and stays on my home timezone. I wish it would check my actual location (GPS?) and update automatically to match where I actually am.
  • Slack: My most distracting friend groupchat is on slack, and there is no good way (as far as I know) to only block my friend slack while not blocking work slack. I solve that on my primary work computer by simply not logging into friend-slack on that machine, but on other devices I use during the work day (most painfully my iPad) it can be a distraction.

Overall this is an amazing product, and if you struggle with digital distractions I highly recommend it.

Writing elsewhere; the pain of moving platforms

I’ve been doing a lot of writing elsewhere of late. Some links:

  • I’ve written a fair amount in the past year for the Tidelift blog, most recently on the EU’s Cyber Resiliency Act and what it might mean for open source.
  • I wrote last week at opensource.com; the latest in a now multi-year series on board candidates in elections for the Open Source Initiative.
  • I have a newsletter on the intersection of open and machine learning at openml.fyi. It is fun!
  • I’ve moved to the fediverse for most of my social media—I’m social.coop/@luis_in_brief (and you can subscribe to this blog via the fediverse at @lu.is/@admin).

I don’t love (mostly) leaving Twitter; as I’ve said a few times, the exposure to different people there helped make me a better person. But one of my primary political concerns is the rise of fascism in the US, and that absolutely includes Elon and the people who enable him. I can’t quit cold-turkey; unfortunately, too many things I care about (or need to follow for work) haven’t left. But I can at least sleep well.

Book Notes: Summer 2022 (burnout and the good life)

I promised in my post on water to blog more this summer. So far, so fail, but in part it’s because I’ve been reading a lot. Some miscellaneous notes on those books follow.

“An interesting bookshelf photorealistic”, as rendered by Midjourney’s image-creation AI, another summer hobby.

Those of you who have emailed my work address lately will have noticed I’m also on sabbatical this summer, because after five years of focus on Tidelift I’m feeling pretty burnt out. This is not a criticism of Tidelift: it’s a great team; I’m very proud of what we are doing; and I will be going back shortly. But a big theme of the summer has been to think about what I want to do, and how that intersects with Tidelift—so that when I come back I’ll be both a strong contributor, and a happy and healthy contributor.

Work—burnout and better futures

The End of Burnout, by Jonathan Malesic: Malesic puts the blame for burnout squarely on our culture rather than us as individuals, which means the book has very few prescriptions for how we as individuals can deal with burnout. But it has interesting meditations on how we can create a culture that mitigates against burnout.

I hope to do a fuller review soon, because I find it difficult to summarize quickly, and much of it applies to open collaborative communities, where the line between self-affirming creation and self-destructive labor can be very fluid. In the meantime, I’ve put some of my favorite quotes up on Goodreads and annotated many of them.

Imaginable, by Jane McGonigal: I found this equal parts fascinating and frustrating. 

Good: it helped me ask “what the hell am I doing” in much better ways. Two key tricks to this: asking it in a ten year timeframe, and using a bunch of neat futurist-y brainstorming techniques to help think genuinely outside of the box. For this reason I think it might end up being, in ten years, the most influential “self-help” book I ever read.

Bad: it’s a classic “this book should have been an article”, and it is the first time I’ve thought “this book should have been an app”—the structured brainstorming exercises could have been much more impactful if guided with even minimal software. There actually is a companion(?) pay-to-enter community, which so far I’ve really enjoyed—if I stick with it, and find value, I suspect in the future I’ll recommend joining that community rather than reading the book.

Other big failure(?): it focuses a lot on What Is Going On In The World and How You Can Change It, when one of my takeaways from Malesic’s burnout book was to focus less on The World and more on the concrete people and places around me. The book’s techniques are still helpful for this, which is why I think it’ll be impactful for me, but I think it’d be a better book if its examples and analysis also drilled down on the personal.

Place

I’ve had the luxury of spending the summer in Bozeman, visiting my sister and nieces/nephew. So a few books on Montana:

History of Montana in 101 Objects: Terrific. Great selection of objects; thoughtful but concise essays. I wish someone would write the same about SF. Highly recommended for anyone who spends time in the state.

Ties, Rails, and Telegraph Wires, by Dale Martin: A thing that is hard to wrap one’s head around when it comes to Montana is the vastness of the place; fourth biggest state, and 7.5 people per square mile. (CA: 254/mi2; SF: 6,200/mi2, The Mission: 30K/mi2.) This book does a lovely job capturing the vast spaces of Montana at the beginning and end of two massive technological changes: the coming of the train and the coming of cars. Bonus: lavishly photographed (largely via the work of Ron Nixon). 

Water, Climate, and Climate Action

A disconnect I’ve been struggling with is between my digitally-focused work and my increasing concerns for/interest in the Real World. Related reads:

Introduction to Water in California, by David Carle: Recommend strongly if you’re a Californian wanting to geek out, but for most the Wikipedia article is probably sufficient.

How To Blow Up A Pipeline, by Andreas Malm: I recommend every citizen of the developed, carbon-dependent world read this. It might not motivate you to commit violence against carbon-generating property, but it will at least put you in the right place to react appropriately when you see reports of such violence against property. There’s a lot to unpack, and again, I recommend reading it, but at the end of the day much boils down to an image from the end of the book: when the author and other allies took down a fence around a brown-coal power plant, even Green party politicians condemned that as “violence”. The emissions of the power plant themselves? Not condemned; not considered violence in our discourse or politics.

Asceticism I didn’t read

In the past, I’ve on occasion turned to a certain sort of philosophical asceticism when in a frustrated place. So I packed these:

Zen and the Art of Motorcycle Maintenance: I liked this book a lot in my teens and 20s, and much of the focus on Quality still resonates with me. I thought it’d be fun to re-read it in Bozeman (where much of the book takes place). But ultimately I haven’t even cracked the cover, because right now I don’t want to retreat to craft, no matter how well done. Instead, an outgoing, community-centric approach to life feels more appropriate.

Meditations of Marcus Aurelius, translated and annotated by Robin Waterfield: Unlike Zen and…, I have started this one, and would highly recommend it—the translation is very accessible and the annotations are terrific. But again, the detached life feels like the wrong route right now—even if it is one that in the past I’ve fallen into very easily.

Fiction

Read a fair bit of fiction over the summer, much of it light, trite, and not worth recommending or even thinking much about. If you want every detail, it’s in my Goodreads feed; the best of it will get added at some point to my mega-thread of diverse science-fiction/fantasy recs over on Twitter.

Water on the brain; joining OpenET board

I’m becoming a Westerner (in an age of aridification) because I have water permanently on the brain.

Quite related, I’ve joined the board of OpenET to help bring open data on evapotranspiration (a key part of the water cycle) to Colorado River water management, and eventually to the whole world. I’ll be advising on both basics like licensing and of course the more complex bits like economic sustainability, where (via Tidelift) my head mostly is these days.

Many thanks to John Fleck (GNOME documentation project, ret.) for dragging my head into this space years ago by writing about it so well for so long.

Broader opens: on the relevance of cryptolaw for open lawyers

I’ve been thinking a lot of late about what “libre” and “open” mean to me, in large part by thinking about movements adjacent to open source software, and how open software might learn/borrow from its progeny. I hope to go into that more this summer, but in the meantime, I’m publishing this as a related “just blog it and get it out” note.

A chart from a recent presentation I gave on legal topics adjacent to open. Security, DAOs, smart contracts, and Swiss non-profits, among others, show up here and stem from, or are more salient in, the crypto space.

This post started as an email to a private list, giving my best-case argument for why open lawyers should pay attention to crypto/blockchain/web3 even if it’s apparent that most of these things are at best naive and at worst planet-destroying scams. I think it’s worth sharing in public to get more comments and more thoughts on this attempt to steel man the argument for cryptolaw.

So, why should open-adjacent lawyers take crypto seriously?

The Bad Bits

Liability

I’ll start with a point designed to appeal to the most diehard crypto-haters (and to be clear, that’s mostly me too!) Quite simply, crypto (particularly but not just smart contracts) is an almost ideal test case for anyone who wants to bring product liability into software. For decades now, we’ve argued (essentially) that software is too complicated, and so software developers should not be liable when it breaks. And in any case, how do you figure out who owes what to whom when it breaks?

In crypto, those arguments start to look particularly weak. The code is much simpler, and the damages are very specific and clear: “my money(-like-thing) disappeared!” And of course this breakage happens all the time; I haven’t looked but I assume there’s an entire category on Web 3 Is Going Great devoted just to software bugs.

Given all this, lawyers will be tempted to bring product liability cases, and judges will be tempted to resolve them. If that happens, and it finally brings serious product liability to software, what does that mean for our FAVORITE BLOCKS OF ALL-CAPS TEXT? To put it another way: the worse you think blockchain is, probably the more worried you should be about the impact of blockchain on every free software license.

(For this point, I am indebted to Mark Radcliffe, who has been writing and speaking on this issue for a while.)

Ethics, or lack thereof

To continue again with the “the more you hate crypto, the more you should pay attention” theme: lots of developers also hate crypto! In the past year I have been repeatedly asked about anti-crypto riders to attach to open source licenses. This would of course make them non-OSI-approved, but lots of developers hate crypto even more than they like (or are aware of) OSI. I suspect that if ethics-focused licenses ever really take off, anti-crypto energy may be the main driver. How those licenses are defined will make a difference, possibly in clauses that live well-past the current crazy.

The Better(?) Bits

Creates lots of code

To turn towards the more positive side: crypto is one of the most dynamic nearly-completely-FOSS sectors out there; it’d be weird for the open community more broadly to ignore them as FOSS consumers and producers. They write a lot of FOSS-licensed code!

As a practical matter, even if you think tokens/blockchain are likely to fail in the long run, it is likely that some of this code will leak back into non-token applications, so its licensing (and related: licensing hygiene) matters.

Governance innovation

Open source communities have traditionally had at least some members interested in how to govern online communities. Many of us who have been around long enough will have participated in more than one discussion of which version of Ranked Choice Voting to use 😭

Crypto is innovating furiously in the online governance space. As with all “innovation” most of that will turn out to be pointless or actively bad. But as a few practical examples of how it is filtering back into open source:

Again, most of that is somewhere between naivete and scam, but not all of it. Open lawyers (and open leaders more generally) should be aware of these ideas and have responses for them.

Taking ‘freedom’ seriously, sometimes

Related to the previous point, as the Cryptographic Autonomy License process reminded us, at least some crypto communities are taking the principles of free software very seriously and extending them to critical future issues like data governance and privacy. If open source wants to move the ball forward on these values and methodologies, the action is by and large in crypto (even if finding the good-faith action is a little bit like finding a needle in a haystack of greed and scams).

‘Smart’ contracts as new legal form?

Smart contracts are mostly garbage (because they are software and most software is garbage) but the interface of this new legal form with existing institutions is both (1) intellectually interesting and (2) has a lot of parallels to early adoption of open licensing as a legal form/tool. I’d love to interview the author of this paper on smart-contracts-as-vending-machines, for example. Similarly, I suspect there is something to be learned from efforts to bring arbitration to the smart contract space.

Money and interest

Finally, there is, quite simply, a pile of crypto-derived money and therefore employment out there. I personally find taking that money pretty distasteful, but lots of friends are taking it in good faith. Every open and open-adjacent lawyer will be getting questions (and many of will be getting paid for their time) out of that pile of money in coming months and years.

Whether we like it or not, this money — and the people paid by it — will set agendas and influence directions. We need to take it seriously even if we dislike it.

Closing (re-)disclaimer

Again: lots of cryptocurrency/web3 is malicious, and the primary legal response to carbon-emitting proof-of-work should be to figure out how to lock people up for it.

But there are, I suspect, a growing number of overlaps between what “we” do in “open” and what “they” are doing “there”. If we want to be seriously forward-looking, we need to take it seriously even if we hate it.

Editing a background check policy

We’re implementing a background check policy for some roles at Tidelift, because we see security-critical information from our customers. Our background check provider (who I won’t name, because this isn’t about them) has a template policy that is pretty good! But the rest of their product has a very high standard for UX—their designers generally do not settle for pretty good.

The red pen bleeds during term paper season... (11/52)
“The red pen bleeds during term paper season… (11/52)” by Rodger_Evans is licensed under CC BY-ND 2.0

Since I know they care, and since employment documents (especially ones that relate to bias) are an important way Tidelift communicate about our company values, I took the time to send them my changes. Having done that work I figured I’d make it a blog post too :) Some notes:

Consistency between software and legal documents

A legal document is, in many cases, a part of a company’s user experience. As such, it needs to be vetted for consistency with the rest of the software, just as you’d vet any other part of the UX.

This is hard, and easy to screw up, because let’s face it—who likes reading and re-reading legal documents? Not even lawyers, if we’re being honest. This particular document screws this up in two ways.

First, the tool (very correctly!) encourages companies not to do a background check for every position, since that introduces a significant bias against people who may have been rehabilitated and should have a fair chance at employment. But the legal document says very plainly that “all offers of employment are contingent on … a background check” (emphasis mine). The legal terms must be brought into alignment with the software’s reality.

Similarly, one of the benefits of this tool is that it takes care of the paperwork for you—without pens and paper. And yet the legal document says that a “signed, written consent will be obtained … in compliance with … law”. Now, good American lawyers know that under the E-SIGN Act of 2000, lots of digital things are “signatures” for the purposes of American law, but most people don’t know that. Good drafting will avoid confusing these non-lawyers by simply saying the consent will be “explicit” and recorded by the service.

Multi-clause sentences and checklists

This is not always the case, but many sentences in legal documents would benefit from being broken up into bullet points, so that each criteria is easier to follow or even treat as a checklist. Consider the difference between:

A decision to withdraw an offer of employment will be made only after conducting an individualized inquiry into whether the information obtained is job-related and a decision to withdraw an offer is consistent with business necessity.  

Original policy

And:

A decision to withdraw an offer of employment will be made only after conducting an individualized inquiry into whether:
– the information obtained through the reference check is relevant to the nature and performance of the role; and
– withdrawal is consistent with the business’s needs.

My revisions

This sounds sort of trivial, but clear writing really can help you spot errors. In this case, breaking up a sentence into bullet points made me notice that the document was inconsistent—an important anti-bias process step was listed in another section, but silently dropped in this list. So someone skimming just the one section of the policy might get it very, very wrong. (Programmers reading this will be nodding along right now—this is debugging by using better formatting to ease code inspection.)

Similarly, where a process is spread across multiple paragraphs, consider using numbered bullet points to emphasize the checklist-like nature of the process and improve the ability to discuss. Much easier to ask “did you do step 4” than “did you do the second clause of the third sentence”.

Q&A style

I continue to believe that many legal documents should at least be edited (not necessarily finalized) in a Q&A style—in other words, changing each section header to a question, and making sure the section actually answers the question. I talked a bit more about that in this post about doing it for a draft of the Mozilla Public License.

In all cases, doing this forces you to make sure that each section has a focused, clear purpose. For example, in the original draft of this policy, there was a section titled “Evaluating Background Check Results”. Revising that into a question (“How will we evaluate the results of the background check?”) helped me realize that one sentence was about a related, but different topic—privacy. Breaking that out into its own privacy section both clarifying the original section and allowed the new section to respond more forcefully to employee concerns about confidentiality.

In the best cases the Q&A framing can really help understanding for non-legal (and even legal) readers. In this case, I found that a well-placed question helped differentiate “why the company does it” from “how the company does it”—which was muddled in the original draft, and important to aid understanding of a tricky anti-bias concept.

Be careful about definitions

Last but not least—you can often tell when a document has suffered from copy/paste when it uses a defined term exactly once, rather than multiple times. Not only does this give you the opportunity to remove the defined term (in this case “Company”) but it also reminds you to give extra focus on the ways that term is used, since it is likely to have copy/paste problems. (In this particular case the stray “Company” thankfully didn’t point to anything worse than jarring word choice—but at least it was easy to eliminate!)

Interested in learning more? Come work with me!

I can’t promise we approach everything with this level of detail; we’re still a small startup and one of the ways we balance the tension between pragmatism and idealism is to Just Get Things Done. But I’m also proud of the way so many of us think through the things some other companies get wrong. If that sounds like fun, we’re hiring!

My teleconf setup

Several friends have asked about my camera/videoconferencing setup, so some notes on that.

Picture from my desktop camera. Lighting isn’t quite as even as I’d like (and as always in stills, my smile is goofy) but you can see the background blur clearly.

Why?

I’ve joked that for lawyers, a good videoconferencing setup is now like a good suit—sort of pointless but nevertheless can help make a good impression in a field where impressions, for better and for worse, matter.

I picked up the new book “Presenting Virtually” from Duarte and it starts with something that’s pretty basic, but also not always obvious—you can’t control networks, and often don’t control what presentation software you’re using. What you do control is your hardware, so make that the best you can.

Camera

I bought a Canon 77D to take baby pictures and… it was in a closet when the pandemic hit. I use it with a 24mm pancake lens. Canon provides a driver that lets you use the camera as a webcam.

Given the cost, I’m not sure this makes sense for most people to do unless they already have a compatible Canon laying around. But if you do have a supported one it works great!

As an alternative, friends speak very highly of this new Dell camera.

Light

I cheat by having good natural light in my office and then supplementing it, rather than having to blast light all over to make up for the gap. This means my light was cheap; the primary criteria was being able to change the color (from a bright white to yellow-ish) so that things looked right.

The exact model I got is no longer available, but is basically similar to this one.

Pro tip for new-ish home workers: if you have two rooms, one dark and one bright, make your bedroom dark and cramped and your office big and light. The previous residents of our place made the reverse choice and I don’t understand it at all.

Microphone

I have a Blue Yeti mic. I’m not sure I’d recommend it for most people. The audio quality is very good, but positioning it over a desk is finicky. (I use these for both my camera and mic, and they work once you get them set up, but they’re a pain.) In addition, it has a headphone jack—which is fine except it insists on reporting to the operating system that it is live even when it has nothing plugged in, so I frequently have to say “no, bad zoom, use the speakers that are actually speakers”.

If I were doing it over again, I’d get something designed more specifically for the home office use case. A friend swears by their Jabra 510, and this new thing from Logitech looks pretty interesting.

What I’m not doing (at least not yet)

I’m sorely tempted to get a teleprompter, but Stephen has mostly convinced me not to. In my experience, at this time, the bar is pretty low—having a good camera and light really does make things noticeably better for people on the other end, even if your eye contact isn’t perfect while doing a slide deck. So you can get a lot of bang for a lot less effort than Stephen spent. Still, tempting some days :)

Hope this is helpful!

Notes on histories: the European nation-state, the Lakota, and Athens

I have been doing a variety of history reading of late, but have not had time to properly synthesize them. They keep coming up in conversation, though, so I wanted to write down some bullet points I could refer to. I hope they are interesting and/or provocative in a good way to someone.

Resemblance to the history of open source was rarely why I read these books. (In fact at least one was read deliberately to get away from open source thinking.) And yet the parallels — around power, mindshare, “territory”, autonomy, empowerment, innovation—keep coming back to me. I leave conclusions, for the most part, for now, to the reader.

Final disclaimer: in the interest of finally publishing a damn thing (I read Ober years ago!), this post will necessarily condense and butcher thousands of pages of scholarship. Please read with that in mind — errors and oversights are almost certainly mine and not the fault of the original authors.

The Sovereign State and Its Competitors, Hendrik Spruyt

This book attempts to understand how Europe got from feudalism to the modern nation-state. It’s explicitly an argument against a view of history where nation-states were inevitable, instead trying to show that there were other possible paths during the late Middle Ages. (The book is very Euro-centric without acknowledging that, which is a shame since I think the book would be well-complemented by an analysis of how European nation-states interacted in colonial settings with non-nation-states, about which more later.)

The core argument goes something like this:

  • what is feudalism anyway? at some level, it means “no entity has a monopoly on power in a territory”, because feudal lords, the church, tribal-like kinship relationships, etc., all overlap and interact in complicated ways.
  • you get out of feudalism, and into nation-states by:
  • punctuated-equilibrium-style evolution: a major shock to existing system (in Spruyt’s analysis, massive economic growth starting in c. 1000) which creates new power centers (bourgeoisie and new cities), which destabilizes feudalism and …
  • creates a diverse set of post-feudal options: wealthy, powerful city-states in Italy; leagues of cities in Germany; something like the modern nation-state in France. (It is this diversity which Spruyt says a lot of historians ignore, and certainly which American high-school history completely ignores.) But…
  • that situation (with a lot of different, competing options) is unstable even if each individual solution makes sense for that place/time (i.e., “city-states were stable in/good for Italy” and “city-states were not stable in/fit for Europe” can both be very true), so then…
  • competition and conscious self-selection leaves you with modern nation-states on top, for a variety of reasons, including simply that nation states prefer negotiating with other nation-states; i.e., hard for France to make treaties with a loose coalition (league) of cities, so it partners with (and therefore empowers) other units like it.

I would love to see a similar analysis for the history of various corporate forms or industries. I’ve seen it suggested, for example, that the combination of the telegraph and the railroad made multi-jurisdiction limited-liability corporations the dominant form in the US, but there was nearly simultaneously a huge explosion in experimentation around cooperatives—should we complicate the “telegraphs → big companies” narrative in the same way Spruyt is attempting to complicate it here for the transition from feudal society to nation-states?

The mapping to open source is probably pretty obvious: internet-enabled development (and then internet-enabled distribution) delivered a shock to the existing software business ecosystem; for a time we had a flourishing of institutional/organizational forms. There is certainly a narrative (perhaps correct? perhaps not?) that we are settling into a new equilibrium with a smaller number of forms. What might this history tell us about where we’re going (and what questions we should ask about the narrative of where we’re going?)

Lakota America: A New History of Indigenous Power, Pekka Hämäläinen

US history books rarely show Native American tribes as entities with agency—the world acts on them, but not vice-versa. This book aims to be an antidote to that, showing over a course of roughly 200 years how the Lakota acted, learned, and changed in response to the world around them (including, but definitely not limited to, the US).

I definitely did not read this with the intent of “oh, this will make me think about open source”; I figured it was about as far away as I could get, and yet as I read I couldn’t help but think about parallels.

I think it’s important to be clear: by drawing parallels here I definitely don’t want to suggest that changes in open source are in any way morally/ethically comparable to genocide; if (free?)/open source culture vanished altogether tomorrow that would be a genuine tragedy, but an extremely minor tragedy compared to the very deliberate genocide that occurred occurred in North America.

But it’s hard not to see parallels in the gradual encirclement and disruption of one culture by another very different culture. Some other thoughts:

  • In one of the many ways in which the book thoughtfully gives the Lakota agency, the author writes of that “[t]hey had welcomed America’s merchandize but not its paternal embrace; they had accepted the Americans as traders and potential allies, but not as their sovereigns. They had, in other words, refused to be ‘discovered’ by [Lewis and Clark]”.
  • Just like in Spruyt’s Sovereign State, much is made of the simply different notions of “territory” between the nation-state and its competitors; in this case, between the Lakota whose governing style the book describes as “ranging widely but ruling lightly… a malleable, forever transmuting regime”, with little attention to borders or even ultimately to control, and the Americans who “were content with a cartographic proof of.. sovereignty”, needing (and imputing power to) lines on a map.
  • Technology is a small but significant undercurrent in the book: first guns, then horses, then ultimately the railroad. The first of these two were enthusiastically adopted by the Lakota, and indeed powered much of their imperial expansion in the 1800s. But they could not adopt the railroad in the same way. Nor was writing, though he does say that “[a] key element of Lakotas’ diplomatic prowess was the fact that they had so many literate allies who interpreted and explained [American] documents for them.”
  • “Contemporary Americans saw the Powder River country as an Indigenous retreat, an insular world intentionally cut off from the rapidly expanding American empire of cities, railroads, settlers, farms, ranches, and capitalism—a perception that has dominated outsider views of the Lakotas ever since. In reality, the Powder River country under the Lakota rule was a safe and dynamic cosmopolitan world of its own where transnational commercial circuits converged, where Indians enjoyed many comforts and advantages of the industrial age, and where new ideas about being in the world were constantly debated. Lakotas knew full well that they lived in a transitional period of innovation, quickening change, and questioning of old conventions. But contrary to the tired old stereotype of obstinate, tradition-bound Indians, they embraced this radical regeneration of their world.”

Additional selected Kindle highlights from my read are here.

Democracy and Knowledge: Innovation and Learning in Classical Athens, Josiah Ober

Ober is a data-driven classicist, focused on Athens and how it fit into the broader milieu of classical Greece. In my distant recollection, this book (or perhaps often just my takeaway from it) argues that:

  • Since you have literally a thousand Greek city states, you’re running a real experiment you can draw real conclusions from. And Athens, in a real material sense (backed by a variety of interesting data sets) “won” this experiment. (This has some parallels to Spruyt, arguing that in essence there was a flourishing of alternatives and then a winnowing.)
  • This greatness was in large part predicated on Athen’s ability as a democracy (relative to its neighbors, at any rate) to create and synthesize effective knowledge. In other words, it was better at being a government specifically because it was a democracy, using “local”/small-group/individual knowledge to make itself more effective.
  • Athens then ultimately failed (after nearly 200 years) in part because neighboring oligarchic governments took its good ideas, and re-implemented them. (This issue is also explored in Ober’s Rise and Fall of Classical Greece.)

I do wish I still had my original notes from reading this a decade or so ago; both it and Rise and Fall are deep and rich books that stirred my political theory bones in a great way.

Governing Values-Centered Tech Non-Profits; or, The Route Not Taken by FSF

A few weeks ago, I interviewed my friend Katherine Maher on leading a non-profit under some of the biggest challenges an org can face: accusations of assault by leadership, and a growing gap between mission and reality on the ground.

We did the interview at the Free Software Foundation’s Libre Planet conference. We chose that forum because I was hopeful that the FSF’s staff, board, and membership might want to learn about how other orgs had risen to challenges like those faced by FSF after Richard Stallman’s departure in 2019. I, like many others in this space, have a soft spot for the FSF and want it to succeed. And the fact my talk was accepted gave me further hope.

Unfortunately, the next day it was announced at the same conference that Stallman would rejoin the FSF board. This made clear that the existing board tolerated Stallman’s terrible behavior towards others, and endorsed his failed leadership—a classic case of non-profit founder syndrome.

While the board’s action made the talk less timely, much of the talk is still, hopefully, relevant to any value-centered tech non-profit that is grappling with executive misbehavior and/or simply keeping up with a changing tech world. As a result, I’ve decided to present here some excerpts from our interview. They have been lightly edited, emphasized, and contextualized. The full transcript is here.

Sunlight Foundation: harassment, culture, and leadership

In the first part of our conversation, we spoke about Katherine’s tenure on the board of the Sunlight Foundation. Shortly after she joined, Huffington Post reported on bullying, harassment, and rape accusations against a key member of Sunlight’s leadership team.

[I had] worked for a long time with the Sunlight Foundation and very much valued what they’d given to the transparency and open data open government world. I … ended up on a board that was meant to help the organization reinvent what its future would be.

I think I was on the board for probably no more than three months, when an article landed in the Huffington Post that went back 10 years looking at … a culture of exclusion and harassment, but also … credible [accusations] of sexual assault.

And so as a board … we realized very quickly that there was no possible path forward without really looking at our past, where we had come from, what that had done in terms of the culture of the institution, but also the culture of the broader open government space.

Katherine

Practical impacts of harassment

Sunlight’s board saw immediately that an org cannot effectively grapple with a global, ethical technological future if the org’s leadership cannot grapple with its own culture of harassment. Some of the pragmatic reasons for this included:

The [Huffington Post] article detailed a culture of heavy drinking and harassment, intimidation.

What does that mean for an organization that is attempting to do work in sort of a progressive space of open government and transparency? How do you square those values from an institutional mission standpoint? That’s one [pragmatic] question.

Another question is, as an organization that’s trying to hire, what does this mean for your employer brand? How can you even be an organization that’s competitive [for hiring] if you’ve got this culture out there on the books?

And then the third pragmatic question is … [w]hat does this mean for like our funding, our funders, and the relationships that we have with other partner institutions who may want to use the tools?

Katherine

FSF suffers from similar pragmatic problems—problems that absolutely can’t be separated from the founder’s inability to treat all people as full human beings worthy of his respect. (Both of the tweets below lead to detailed threads from former FSF employees.)

Since the announcement of Stallman’s return, all top leadership of the organization have resigned, and former employees have detailed how the FSF staff has (for over a decade) had to deal with Richard’s unpleasant behavior, leading to morale problems, turnover, and even unionization explicitly to deal with RMS.

And as for funding, compare the 2018 sponsor list with the current, much shorter sponsor list.

So it seems undeniable: building a horrible culture has pragmatic impacts on an org’s ability to espouse its values.

Values and harassment

Of course, a values-centered organization should be willing to anger sponsors if it is important for their values. But at Sunlight, it was also clear that dealing with the culture of harassment was relevant to their values, and the new board had to ask hard questions about that:

The values questions, which … are just as important, were… what does this mean to be an organization that focuses on transparency in an environment in which we’ve not been transparent about our past?

What does it mean to be an institution that [has] progressive values in the sense of inclusion, a recognition that participation is critically important? … Is everyone able to participate? How can we square that with the institution that are meant to be?

And what do we do to think about justice and redress for (primarily the women) who are subjected to this culture[?]

Katherine

Unlike Sunlight, FSF is not about transparency, per se, but RMS at his best has always been very strong about how freedom had to be for everyone. FSF is an inherently political project! One can’t advocate for the rights of everyone if, simultaneously, one treats staff disposably and women as objects to be licked without their consent, and half the population (women) responds by actively avoiding the leadership of the “movement”.

So, in this situation, what is a board to do? In Sunlight’s case:

[Myself and fellow board member Zoe Reiter] decided that this was a no brainer, we had to do an external investigation.

The challenges of doing this… were pretty tough. [W]e reached out to everyone who’d been involved with the organization we also put not just as employees but also trying to find people who’ve been involved in transparency camps and other sorts of initiatives that Sunlight had had run.

We put out calls for participation on our blog; we hired a third party legal firm to do investigation and interviews with people who had been affected.

We were very open in the way that we thought about who should be included in that—not just employees, but anyone who had something that they wanted to raise. That produced a report that we then published to the general public, really trying to account for some of the things that have been found.

Katherine

The report Katherine mentions is available in two parts (results, recommendations) and is quite short (nine pages total).

While most of the report is quite specific to the Sunlight Foundation’s specific situation, the FSF board should particularly have read page 3 of the recommendations: “Instituting Board Governance Best Practices”. Among other recommendations relevant to many tech non-profits (not just FSF!), the report says Sunlight should “institute term limits” and “commit to a concerted effort to recruit new members to grow the Board and its capacity”.

Who can investigate a culture? When?

Katherine noted that self-scrutiny is not just something for large orgs:

[W]hen we published this report, part of what we were hoping for was that … we wanted other organizations to be able to approach this in similar challenges with a little bit of a blueprint for how one might do it. Particularly small orgs.

There were four of us on the board. Sunlight is a small organization—15 people. The idea that an even smaller organizations don’t have the resources to do it was something that we wanted to stand against and say, actually, this is something that every and all organizations should be able to take on regardless of the resources available to them.

Katherine

It’s also important to note that the need for critical self scrutiny is not something that “expires” if not undertaken immediately—communities are larger, and longer-lived, than the relevant staff or boards, so even if the moment seems to be in the relatively distant past, an investigation can still be valuable for rebuilding organizational trust and effectiveness.

[D]espite the fact that this was 10 years ago, and none of us were on the board at this particular time, there is an accounting that we owe to the people who are part of this community, to the people who are our stakeholders in this work, to the people who use our tools, to the people who advocated, who donated, who went on to have careers who were shaped by this experience.

And I don’t just mean, folks who were in the space still—I mean, folks who were driven out of the space because of the experiences they had. There was an accountability that we owed. And I think it is important that we grappled with that, even if it was sort of an imperfect outcome.

Katherine

Winding down Sunlight

As part of the conclusion of the report on culture and harassment, it was recommended that the Sunlight board “chart a new course forward” by developing a “comprehensive strategic plan”. As part of that effort, the board eventually decided to shut the organization down—not because of harassment, but because in many ways the organization had been so successful that it had outlived its purpose.

In Katherine’s words:

[T]he lesson isn’t that we shut down because there was a sexual assault allegation, and we investigated it. Absolutely not!

The lesson is that we shut down because as we went through this process of interrogating where we were, as an organization, and the culture that was part of the organization, there was a question of what would be required for us to shift the organization into a more inclusive space? And the answer is a lot of that work had already been done by the staff that were there…

But the other piece of it was, does it work? Does the world need a Sunlight right now? And the answer, I think, in in large part was not to do the same things that Sunlight had been doing. …

The organization spawned an entire community of practitioners that have gone on to do really great work in other spaces. And we felt as though that sort of national-level governmental transparency through tech wasn’t necessarily needed in the same way as it had been 15 years prior. And that’s okay, that’s a good thing.

Katherine

We were careful to say at Libre Planet that I don’t think FSF needs to shut down because of RMS’s terrible behavior. But the reaction of many, many people to “RMS is back on the FSF board” is “who cares, FSF has been irrelevant for decades”.

That should be of great concern to the board. As I sometimes put it—free licenses have taken over the world, and despite that the overwhelming consensus is that open won and (as RMS himself would say) free lost. This undeniable fact reflects very badly on the organization whose nominal job it is to promote freedom. So it’s absolutely the case that shutting down FSF, and finding homes for its most important projects in organizations that do not suffer from deep governance issues, should be an option the current board and membership consider.

Which brings us to the second, more optimistic topic: how did Wikimedia react to a changing world? It wasn’t by shutting down! Instead, it was by building on what was already successful to make sure they were meeting their values—an option that is also still very much available to FSF.

Wikimedia: rethinking mission in a changing world

Wikimedia’s vision is simple: “A world in which every single human can freely share in the sum of all knowledge.” And yet, in Katherine’s telling, it was obvious that there was still a gap between the vision, the state of the world, and how the movement was executing.

We turned 15 in 2016 … and I was struck by the fact that when I joined the Wikimedia Foundation, in 2014, we had been building from a point of our founding, but we were not building toward something.

So we were building away from a established sort of identity … a free encyclopedia that anyone can edit; a grounding in what it means to be a part of open culture and free and libre software culture; an understanding that … But I didn’t know where we were going.

We had gotten really good at building an encyclopedia—imperfect! there’s much more to do!—but we knew that we were building an encyclopedia, and yet … to what end?

Because “a free world in which every single human being can share in the sum of all knowledge”—there’s a lot more than an encyclopedia there. And there’s all sorts of questions:

About what does “share” mean?

And what does the distribution of knowledge mean?

And what does “all knowledge” mean?

And who are all these people—“every single human being”? Because we’ve got like a billion and a half devices visiting our sites every month. But even if we’re generous, and say, that’s a billion people, that is not the entirety of the world’s population.

Katherine

As we discussed during parts of the talk not excerpted here, usage by a billion people is not failure! And yet, it is not “every single human being”, and so WMF’s leadership decided to think strategically about that gap.

FSF’s leadership could be doing something similar—celebrating that GPL is one of the most widely-used legal documents in human history, while grappling with the reality that the preamble to the GPL is widely unheeded; celebrating that essentially every human with an internet connection interacts with GPL-licensed software (Linux) every day, while wrestling deeply with the fact that they’re not free in the way the organization hopes.

Some of the blame for that does in fact lie with capitalism and particular capitalists, but the leadership of the FSF must also reflect on their role in those failures if the organization is to effectively advance their mission in the 2020s and beyond.

Self-awareness for a successful, but incomplete, movement

With these big questions in mind, WMF embarked on a large project to create a roadmap, called the 2030 Strategy. (We talked extensively about “why 2030”, which I thought was interesting, but won’t quote here.)

WMF could have talked only to existing Wikimedians about this, but instead (consistent with their values) went more broadly, working along four different tracks. Katherine talked about the tracks in this part of our conversation:

We ran one that was a research track that was looking at where babies are born—demographics I mentioned earlier [e.g., expected massive population growth in Africa—omitted from this blog post but talked about in the full transcript.]

[Another] was who are our most experienced contributors, and what did they have to say about our projects? What do they know? What’s the historic understanding of our intention, our values, the core of who we are, what is it that motivates people to join this project, what makes our culture essential and important in the world?

Then, who are the people who are our external stakeholders, who maybe are not contributors in the sense of contributors to the code or contributors to the projects of content, but are the folks in the broader open tech world? Who are folks in the broad open culture world? Who are people who are in the education space? You know, stakeholders like that? “What’s the future of free knowledge” is what we basically asked them.

And then we went to folks that we had never met before. And we said, “Why don’t you use Wikipedia? What do you think of it? Why would it be valuable to you? Oh, you’ve never even heard of it. That’s so interesting. Tell us more about what you think of when you think of knowledge.” And we spent a lot of time thinking about what these… new readers need out of a project like Wikipedia. If you have no sort of structural construct for an encyclopedia, maybe there’s something entirely different that you need out of a project for free knowledge that has nothing to do with a reference—an archaic reference—to bound books on a bookshelf.

Katherine

This approach, which focused not just on the existing community but on data, partners, and non-participants, has been extensively documented at 2030.wikimedia.org, and can serve as a model for any organization seeking to re-orient itself during a period of change—even if you don’t have the same resources as Wikimedia does.

Unfortunately, this is almost exactly the opposite of the approach FSF has taken. FSF has become almost infamously insulated from the broader tech community, in large part because of RMS’s terrible behavior towards others. (The list of conference organizers who regret allowing him to attend their events is very long.) Nevertheless, given its important role in the overall movement’s history, I suspect that good faith efforts to do this sort of multi-faceted outreach and research could work—if done after RMS is genuinely at arms-length.

Updating values, while staying true to the original mission

The Wikimedia strategy process led to a vision that extended and updated, rather than radically changed, Wikimedia’s strategic direction:

By 2030, Wikimedia will become the essential infrastructure of the ecosystem of free knowledge, and anyone who shares our vision will be able to join us.

Wikipedia

In particular, the focus was around two pillars, which were explicitly additive to the traditional “encyclopedic” activities:

Knowledge equity, which is really around thinking about who’s been excluded and how we bring them in, and what are the structural barriers that enable that exclusion or created that exclusion, rather than just saying “we’re open and everyone can join us”. And how do we break down those barriers?

And knowledge as a service, which is without thinking about, yes, the technical components of what a service oriented architecture is, but how do we make knowledge useful beyond just being a website?

Katherine

I specifically asked Katherine about how Wikimedia was adding to the original vision and mission because I think it’s important to understand that a healthy community can build on its past successes without obliterating or ignoring what has come before. Many in the GNU and FSF communities seem to worry that moving past RMS somehow means abandoning software freedom, which should not be the case. If anything, this should be an opportunity to re-commit to software freedom—in a way that is relevant and actionable given the state of the software industry in 2021.

A healthy community should be able to handle that discussion! And if the GNU and FSF communities cannot, it’s important for the FSF board to investigate why that is the case.

Checklists for values-centered tech boards

Finally, at two points in the conversation, we went into what questions an organization might ask itself that I think are deeply pertinent for not just the FSF but virtually any non-profit, tech or otherwise. I loved this part of the discussion because one could almost split it out into a checklist that any board member could use.

The first set of questions came in response to a question I asked about Wikidata, which did not exist 10 years ago but is now central to the strategic vision of knowledge infrastructure. I asked if Wikidata had been almost been “forced on” the movement by changes in the outside world, to which Katherine said:

Wikipedia … is a constant work in progress. And so our mission should be a constant work in progress too.

How do we align against a north star of our values—of what change we’re trying to effect in the world—while adapting our tactics, our structures, our governance, to the changing realities of the world?

And also continuously auditing ourselves to say, when we started, who, you know, was this serving a certain cohort? Does the model of serving that cohort still help us advance our vision today?

Do we need to structurally change ourselves in order to think about what comes next for our future? That’s an incredibly important thing, and also saying, maybe that thing that we started out doing, maybe there’s innovation out there in the world, maybe there are new opportunities that we can embrace, that will enable us to expand the impact that we have on the world, while also being able to stay true to our mission and ourselves.

Katherine

And to close the conversation, I asked how one aligns the pragmatic and organizational values as a non-profit. Katherine responded that governance was central, with again a great set of questions all board members should ask themselves:

[Y]ou have to ask yourself, like, where does power sit on your board? Do you have a regenerative board that turns over so that you don’t have the same people there for decades?

Do you ensure that funders don’t have outsize weight on your board? I really dislike the practice of having funders on the board, I think it can be incredibly harmful, because it tends to perpetuate funder incentives, rather than, you know, mission incentives.

Do you think thoughtfully about the balance of power within those boards? And are there … clear bylaws and practices that enable healthy transitions, both in terms of sustaining institutional knowledge—so you want people who are around for a certain period of time, balanced against fresh perspective.

[W]hat are the structural safeguards you put in place to ensure that your board is both representative of your core community, but also the communities you seek to serve?

And then how do you interrogate on I think, a three year cycle? … So every three years we … are meant to go through a process of saying “what have we done in the past three, does this align?” and then on an annual basis, saying “how did we do against that three year plan?” So if I know in 15 years, we’re meant to be the essential infrastructure free knowledge, well what do we need to clean up in our house today to make sure we can actually get there?

And some of that stuff can be really basic. Like, do you have a functioning HR system? Do you have employee handbooks that protect your people? … Do you have a way of auditing your performance with your core audience or core stakeholders so that you know that the work of your institution is actually serving the mission?

And when you do that on an annual basis, you’re checking in with yourself on a three year basis, you’re saying this is like the next set of priorities. And it’s always in relation to that that higher vision. So I think every nonprofit can do that. Every size. Every scale.

Katherine

The hard path ahead

The values that the FSF espouses are important and world-changing. And with the success of the GPL in the late 1990s, the FSF had a window of opportunity to become an ACLU of the internet, defending human rights in all their forms. Instead, under Stallman’s leadership, the organization has become estranged and isolated from the rest of the (flourishing!) digital liberties movement, and even from the rest of the software movement it was critical in creating.

This is not the way it had to be, nor the way it must be in the future. I hope our talk, and the resources I link to here, can help FSF and other value-centered tech non-profits grow and succeed in a world that badly needs them.