Silently resolved ambiguity is comprehension debt of intent

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In our theory, the development lifecycle is compressed, and the decisions that are made at “transition” points are moved to later. Even “transition” here is a bit nebulous, as stages of the lifecycle are overlapping more and more with each other. So instead, the types of decisions being made with AI tooling (and the debt they incur) is different. Decisions made with awareness reduce comprehension debt but incur naps; decisions you allow (intentionally or accidently) your agent to make prevent the nap but increase debt. Decide which decisions you should be making, and set your system up to surface them to you alongside relevant data.

The development lifecycle in the "double diamond" structure, with empathy starting small and expanding. Next is defining, which picks up big where empathy left off, and hones down. At that decision point, a problem definition is created. Ideation again expands the space, and an architectural decision record hands off to the prototyping stage, which starts to narrow the space down again. Finally, testing finishes out that point and the decision is whether or not to ship.
Empathy still expands and hands off to a defining stage. However, the definition stage is truncated and moves to a broader ideation stage with a problem definition that is broader. Testing begins in a narrow but straight shot in ideation, soon followed by and overlapping with a broad prototyping stage. When ideation completes, an ADR and goal document is written. Prototyping continues to its truncated point, and then testing finishes out and the final decision point of shipping still exists.
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Organizational size and maturity

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One thing I didn’t understand during my job hunt was how much organizational size and maturity matter for a person’s fit on their new team. Which is funny, considering how much I care about organizational theory and what different organization structures mean about scalability. But, as I geared up to hire backfill for my team, I realized how much I would be setting someone up to fail if they weren’t a good fit in these ways. Someone might be exactly the right personality to fit onto the team, but if the type of change available to them doesn’t suit their proclivities, they’ll feel unsupported and/or stymied in having an impact. There are two vectors here I think are worth talking about, and a few different “levels” within each.

Rule of Threes

There is a pattern in organizational theory (I haven’t found one good catch-all for different things here about how things change at different scales. I might write up more at some point), but in short, your organizational approach changes dramatically each time your size shifts by x3, with the in between being wishy-washy.

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Capitalism isn’t inevitable and it isn’t permanent

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“We live in capitalism. Its power seems inescapable. So did the divine right of kings. Any human power can be resisted and changed by human beings.” — Ursula K. Le Guin

Orroborus, the snake eating its own tail

Oligarchy and capitalism are literally burning up our world. A small few dozen people hold decision-making that impact the entire world. Some of that is locked behind “fiduciary responsibility,” but even the number of those holding stocks in corporations has been skewing wildly. I don’t think I need to sell my audience on all this, so I’ll just leave this point here. The question is: “what can we do differently?”

I think of this in three phases, which are all deeply linked to each other: how do we take hoarded wealth away from those who have it; how do we redistribute in a way that responsibly shifts, rather than all-out collapses, our existing systems; and what does living in the new world look like? There’s a bonus question of how to prevent future hoarding from happening embedded in each of these.

Socialism has some of this. I’d agree the Soviets had it the most right to date. Anarchism warns us away from hoarding power, and wealth as power. Ostrom talks about how there is a third, secret option that is neither markets nor surveillance for allocating resources. Pikkety talks about how we’re well past every other threshold for violent revolution based on inequality. And so what would it look like for us to throw off these chains and do something more care-full, more labor-forward, more “no war but the class war“? Can we do it with minimal suffering incurred, and a more stable outcome?

A triangle with socialist democrats at one point, anarchists at a second, and communists at the third. Socialists and anarchists share participatory decision making, anarchists and communists revolution, and communists and socialists share state power.
Margaret Killjoy made this great chart

I don’t think I have all the answers. I also believe that solidarity is born out of shared work, and shared work begins with being in conversation with each other. So join me on Sept 11 for a salon on what wealth redistribution might look like.

The interest rate on comprehension debt is set by how well relevant information survives

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In the last post, we talked about how debt is an instrument, not a smell. We carry forward the intentionality and the financial metaphor into the thinking for this post.  

In particular, we want you to remember 

  1. Mark’s metaphor of “AI companies that sell coding agents are the equivalent of predatory credit card companies offering introductory cards on college campuses to freshmen.”
  2. Comprehension debt as a new and higher interest-rate loan. “Every agent is the new hire on day one, forever.”
  3. “The Last Responsible Moment” needs to account “for ‘holding costs’ [to] curtail sidequests and keep your project running tightly and in its desired direction.”

Building from these cornerstones, this post asks “if that’s comprehension debt, can we just not take on any? Can we pay for all of our understanding now, in cash?” The answer is “no,” for three reasons we’ll get into.

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Agents and Acquiring Debt

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I had a lovely chat with Kate Chapman and Tom Henderson recently, where we discussed how the shape of technical debt is changing as people become “genie wranglers” and “robot life coaches” (their clever terms, not mine). Specifically, what does using AI mean about addressing pre-AI and accruing post-AI technical debt. Our main takeaway from this session is that commitments should happen at “the last responsible moment,” and AI pushes that moment later.

Human context: Cowritten with Tom and some AI agents; lovingly curated, proofread, and fact-checked by us humans, including Mark. We’re still exploring these ideas, so very much consider this open for feedback. We tried to bridge our academic approach with making things useful in a business sense. We are assuming you have made it past the “spicy autocomplete” phase of using LLMs in your work for this piece. It’s up to you how much you care about code quality for the purposes of this piece, but we think we’ll get into that in a potential later piece. In this article/series, we assume debt is taken on intentionally. This is often not the case, but that is a different problem space than the one we intend to explore.

AI technical debt is different from software debt because it shifts when commitments can be made in the arc of gathering information. We have historically taken on debt early in order to realize some value sooner. Now, we can gather information more cheaply earlier (in theory), and make our difficult-to-change decisions later. That changes the type of debt we’re taking on. It also makes testing even more necessary. You won’t be surprised to know that we’re highlighting and contributing to human judgement throughout, rather than trying to replace the humans. We hint a bit at product commitment points-in-lifecycles and decision making throughout this post, but we said NO to that side quest (for now).

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Moving towards “enough”

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Alongside emergent organizing (which I also have a bone to pick with), there has been a lot of talk about “abundance mindset.” It never sat very well with me. I tried in 2024 to make it my phrase of the year, to try to understand and move towards it, because it’s seemed to important to people I respect. I failed out that year, and have continued to fail out since. 

The thing that doesn’t sit right with me, I realized after lingering with it, is that it reminds me too much of Trickle Down Economics. If someone has more than enough, the thinking goes, they will use the wisdom by which they came to have so much to share with others and uplift all. But as history has proved out, Regan was a right cunt about this and other things. It just doesn’t work that way. Elon Musk has true abundance, and none of us (should) strive to be like him.

I’m also not interested in simply making do with whatever we have access to. That way lies tolerated inequity and “fuck you got mine.”

I am instead more and more deeply invested in understanding, striving for, and then being satisfied with “enough.” I like the life I have. It is a bit more than enough. I no longer feel guilt about having enough, while continuing to have an intrinsic desire to be sure others have enough, too. Not just enough to survive. But also not more than makes sense. 

Our earth is full of limited resources. Our time is limited. Our access to resources and time should be limited as well, then, while being sure we’re getting enough. 

So I wonder — what is “enough” for you? Do you have it? What does rebalancing to “enough” look like for you? What would it mean for the people around you? For the planet?

Textrovert

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A long-time friend and fellow academic nerd is working on her pHd, and had some questions for me. One was “Do you think of relationships that are almost entirely text based as real? Or even entirely text-based? Like things you’re never going to meet this person. Are those real relationships, too?” and Wow but I have Feelings on this one.

  1. I am grateful for all the friends I have all over the world. I think sustained relationships have as much to do with preferred modes of communication as shared interests. I have gone years without “talking” to people I love, all while keeping up in a heart-felt way.
  2. I love live blogging with other people in collaborative documents. I think there is a humor unique to being in a shared text space at the same time, honing in on what someone is trying to say (successfully or otherwise). The best sort of back channeling. I will forever remember typing into a doc with the Civic crew, 7 minutes into a rambling talk, “Have they actually said anything yet?”
  3. One of my oldest x closest friends and I will text each other from the same room, because it’s the form we both prefer, and we’re both funnier in text than in voice. On a community Slack with an #awkward-silence channel, I once posted an elephant emoji. The elephant was immediately removed by a moderator and made the subject of the channel.
  4. Another old, dear friend, who is also an ex, has referred to me lovingly as a “textrovert,” which I have adopted and use widely.

I was quick to vehemently say “of course.”

Then she asked me what that meant about relationships with LLMs. And I kind of went off. Because the “relationships” people have with LLMs has so much less to do with format and so much more to do with what a “friend” is and is not.

I have at least one friend I have kept from every stage of my life, so I think I can comment on this a bit. I have two friends I have had since preschool (and the following 9 years of Catholic school). I have remained friends with coworkers, exes, and people on other continents. If I may be so bold, friendship is kind of my superpower, and I’m damn proud of it. I’m not perfect at it, but I invest in it and it has paid me back multi-fold.

I’m not perfect at it… and that’s the point of this post. Because any long-lived relationship will have some History to it. It will have the time I fucked up and made someone angry or hurt, and visa versa. But for each of these relationships, we called each other in, came back to the table, and built a bigger table. A sycophantic LLM is not interested in how you can be a better person, it’s “interested” in appeasing the most people possible so people think they enjoy using it.

As Priceless enters our 20th year (I’ve been with the group for 10), we have been working to continue our historic ties to strong opinions lightly held. We lose some folks as they onboard with us, as they’re not used to arguments amongst friends. But we all always know we have each other’s backs, and that arguing isn’t personal, and that we’re stronger because we criticize each other’s ideas. This is one of the things I miss most about the Boston Area. The Bay Area seems to think you have to agree with someone to be friendly. And that is absolutely not the core of my friendships.

It’s like when I was reading Love and Sex with Robots… there’s a question of the overlap of sex and masturbation. If informed consent can’t be given, then all you’re doing is masturbating with something you think is an object. And all people who think they’re forming relationships with LLMs are doing is masturbating. Doing so is enjoyable, but it doesn’t prepare you for actual relationships with your fellow humans, and that is to your deep detriment.

If you also have opinions on this (and other things!) let me know and I’ll put you in touch with Alex for her research.

A 4yo who comes down, dressed, within a 10-minute window

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We sure do like routine and structure in this house. We live and die by our shared calendar. Reed and I have a Discord with 26 channels in it. We’re constantly setting and using checklists and reminder functions. We clean before the housekeepers come every other week. It’s kind of A Lot, and while we don’t expect other people to be this die-hard, we did introduce a child into this environment, with all its pluses and minuses. I feel like the living room will never truly be fully tidy for at least the next 14 years. And a child is far more chaotic than fits into the structures we had in place.

When I was pregnant with Locke, we talked about what we would optimize for, to help prepare us for less failure during the first 18 months of sleep deprivation. We decided to optimize for Locke’s sleep above all else. We read Healthy Sleep Habits, Happy Child as recommended by a sweetie of mine who has twin boys and had to survive that. We decided to live by the book religiously. Locke had a rigid sleep schedule that came at great cost to literally the rest of our lives. We had plans within plans if a nap time wasn’t going to be easy, or if one didn’t go according to plan. Locke now has a deeply positive relationship with sleep, including things like Halloween night when we had decided to let him stay up past bedtime declaring 10 minutes past lights out that he was ready for bed and didn’t want any more partying or candy.

We also got a Mella light clock for his room starting while he was still in the crib. He learned that the light turned yellow 30 minutes before we came in, and green when we came in. We had alarms set to be sure our entering coincided within a couple minutes of the light turning green to have a strong association. That then turned into 30 minutes of quiet playtime in his room, and it being ok to leave his room when the light turned green.

But then we had a child who enjoyed quiet playtime so much that he’d just stay in his room indefinitely, and we’d be late to preschool. So we added in an additional system, a clock with just a minute hand, yellow and green along the outside to match the color change clock, and a red line at the 10 minutes of green mark.

The clock is as described in the blog post. A local map is to the left, and a map of California to the right. Below it is the menu for our lunch with a Japanese family.

So the deal is, that if he gets himself dressed and out of his tidied room before the minute hand hits the red line, we will read a bit (currently the complete Calvin and Hobbes) or watch a LEGO video with him. And so our child, who also puts away his own laundry and often helps fold it, will get himself ready, play quietly for awhile, put his things away, and then come downstairs in a 10 minute window in the morning. He seems to enjoy having so much autonomy, and we enjoy having things run so smoothly. And we all enjoy getting a bit of unrushed, planned together time in the mornings.

Japan 2026

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There’s this woman an ex partner left me for. I had moved to the Bay Area in part based on this relationship, but in 2016 my job fell apart, which led to a conversation about how serious the relationship was, and the answer was that it shouldn’t exist. While he and I are back on speaking terms, the gent was essentially doing serial monogamy under the label of relationship anarchy, and it was a mess. Morgan and I, however, continue to get on quite well. I even signed as witness on her recent wedding to an incredible human named Jeff. Morgan and Jeff were going to Japan this year, and invited us to go family traveling with them. The exchange rate is amazing right now, so we jumped at the chance.

Japan was such a lovely place to bring a kid. While they have a history of doing a better job of helping their kids be appropriate in various social settings, the experience was universally accommodating for our kiddo, too. Our travel companions weren’t comfortable breast feeding in public, and we didn’t see a lot of infants out, but children are generally given a lot of independence counterbalanced with high expectations and guidance. Being there really bolstered Locke’s confidence and curiosity.

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Scavenger Hunt Radio Etiquette Game

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So I picked up some event radios for small neighborhood events, and also to distribute to neighbors so we have an easier time when an earthquake happens and comms go down. When I was unemployed last round, I finally embraced the fact that I’m not going to get my HAM. Yes, I know it’s “so easy,” yes I know it’s “so useful.” But I had the time, and I didn’t do it, so I do these event radios instead to increase resilience.

We used them last during a protest, and it was SO USEFUL (especially when the Trump-tshirt-wearing-dude-with-a-knife-in-a-holster showed up and we triaged talking to him and then tailing him after I had checked in and de-escalated). So, we love these things.

But my crew are so very bad new at radio etiquette. It’s a mess, because we don’t talk to each other very often on them. Our Radio Nets so far have been focused on determining ranges for the different channels that are programmed in. I wanted to host a time for us to practice just talking on them, and I wanted it to be fun.

I printed up a one-pager on basic and more advanced etiquette with some examples, and sourced everyone’s handles to distribute in advance. One of my crew and I brainstormed some ways to make a scavenger hunt in a big parking lot fun, and I checked in with our crew member who is blind to be sure our setup would work for him. Here’s what we did.

Hide your things

It’s a scavenger hunt. Hide your things within and area that’s walkable. This will also mean it will be within easy radio range. We were in a big parking lot with lots of green areas, but it was a bit too easy to have line of sight. Better to have nooks and crannies. We hid 11 objects for 9 people on 3 teams to find over the course of an hour.

The task

The thing to do is for each team to find an object and then not pick it up. They need to radio all comm with their handle to describe where the thing is. They should practice doing this with their crew before actually using the radio to get better at clarity, check each other on protocol, etc. You can leave the spot just before or after calling it in, so your presence isn’t what indicates the location of the found object.

Then another team or person tries to find it based on that instruction. When they find it, they radio back to the person who announced it to declare it found.

Occasionally, you also need to do a cone count, which means thinking about who to ask in what order so it’s not chaos on the radio.

Our experience

We had a ton of fun! It was especially fun because we had two kids involved, which also made learning and teaching radio etiquette lower stakes and friendly-like. Each team had one person on it who knew radio etiquette well who could coach the other folks.

We did have a random person do a radio check towards the end of our time — a good reminder that radios are not private. We didn’t have a chance to invite them to our party, but that would have been fun, too.

Next time

The time and setup was about right. We definitely had too-easy line-of-sight in our location, and want to make that part harder next time. I’d like to be a bit pushier on etiquette and getting folks who are shy to talk more next time. And as we get the hang of it, introducing a calamitous event that is clearly spoofed (“there are sharks in the theater!”) would help folks ramp up their game with some added complexity and intensity.