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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.

How much to pay, when

Decision capacity is the budget constraint regardless of when the decisions happen. 

  1. Sure, we’re developing faster now, but the work still needs to be verified before customers see it if you hope to retain trust. 
  2. That validation is taking more time now, not less. 
  3. Future You might know more about the situation you’re developing for, but less and less about how your product works under the hood. 

Where and when are you going to make which decisions over the product lifecycle? When and how will you pay down your comprehension debt by learning how the system works now? AI spins up an unending amount of decision points, especially if you’re using it as we recommend (experiments in early stages as a way of alleviating traditional technical debt). 

Decisions take executive function, and are exhausting in aggregate1;. Every “LGTM” is a micro-loan; but replacing them all with real review would mean slowing down and making lots of decisions. So don’t just shift your Last Responsible Moment to later at the cost of making a bunch of new decisions now, design so you’re making fewer decisions, better, at necessary points. 

Example: Tom’s agents spend a lot of their tokens doing technical art: abstract images derived from free play with mathematically defined fields and symmetries which react in realtime to sensors and music (which is also reacting to sensors). The agent handles the coding decisions, and Tom declares whether the aesthetics work or not. Tom has to set up his pipeline in a way that his decisions are easy to make, surfaced at the right points in time, and easy to adjust for (reduced implementation time based on tech debt being lightweight). 2

What to do instead

A lot of agent outputs are experiments. Full comprehension of this throwaway code is buying insurance on a rental. Instead, query the experiments based on what you were trying to figure out when you designed them, and what you anticipate caring about moving forward. Which architectural approach has the fewest security issues? Which is the most modular? You can even ask the agents to remove decisions for you based on parameters you’ve put in place, and surface only the most promising two or three routes forward, with “reasoning.” This reduces the delta between what’s being decided on and the comprehension we have of it.

Example: Tom did not actually know what mathematical algorithm would give “dystopian.” So he followed this playbook:

  1. Generation — Agents run free-play generation, constrained only by the markdown notes on what Tom’s aesthetic is, and produce dozens of images
  2. Judgement – Every piece auto-renders to a thumbnail, laid out as a grid of small-multiples. Tom doesn’t look at the code at all. 
  3. Promotion –  He picks the 2-3 that kind of work, and snapshots the code that produced them into a database. 
  4. Development – The image that code generates gets opened in a live environment. He requests new code changes or tunes the parameters with a MIDI instrument until the art is satisfying.

There are two things we think come into carrying forward relevant choices into future loops so you don’t have to keep making those choices (unless you want to):

Context

What is relevant for the AI to know based on what you’re currently asking it to do? Context windows aren’t indefinite, and so picking and choosing what context to surface is important. In our session together, we talked about a “Document of Documents” or an Index with reasoning about when each item is relevant, so your agent can pick the right things at the right times. In human orgs, we call this Organizational Folklore, and it sometimes remembers things the humans have rightfully forgotten – “we can’t do it that way because it never works” is actually out of date but no one checked against new realities. Your agent will need to be told to forget such things as well.

Constraints

We talked about three different forms of constraints, each of which should be approached with intentionality:

  1. Iron Ring constraints (load-bearing ethics and the laws of physics, sometimes at the same time), 
  2. “we’ve always done it this way” fossils, and 
  3. constraints nobody meant mentioned in passing, taken by the agent as binding, and nobody knew it was there to consider removing it.3

Constraints should be aligned with your problem space so far as what can’t go wrong while leaving space for path exhaustion/creativity.

The Rate is Negotiable

This is the title’s claim: the interest rate on comprehension debt is set by how well the relevant information survives. Carrying forward relevant knowledge at the right scale of loop is what gets your code towards “less wrong” and more towards something you can understand and/or build upon for longer because it behaves in a predictable way by following constraints you’ve agreed to or put in place. The debt will still exist, but you get to determine how extreme it becomes over time (and therefore what future options you have) by being intentional about this. 

What this means

Last time we talked about comprehension debt as more like a payday loan. That metaphor still applies to vibecoding, LGTM hypnosis, and amnesiac deferral. We hope this post helped you see past the context horizon and to start looking to “when I expand this off of my machine” and pitching to the next person. If decisions are limited rather than proliferated, comprehension debt becomes a line of credit instead of a payday loan, and the question becomes about if it is secured or unsecured. Your collateral are your recorded decisions integrated into your system: Architecture Decision Records (ADRs), folklore that survives, the harness. 

And that means, we need to talk about Looping on Loops. Next post!

Footnotes

  1. The nap is real — see Yegge’s “Nap Attacks.” 
  2. For a performance at Georgetown Steam Plant, Tom and his team were told a theme (“Dystopia All The Way Down”) and a time, but they had no further information about what the space would look like. What are the responsible moments to make decisions in this situation? The dystopic theme and watery sound world (from one of his collaborators) was known weeks in advance, so he developed the static images around the idea of a surveilling eye wreathed in toxic smoke, but near a peaceful oceanside. The ambient lighting wouldn’t be known until the moment of arrival, so in those weeks he chose on-theme but high-chroma colors, readable when projected in a high-ambient light situation. The data pipeline was complete a week in advance, so he took a recording of sensor events in a rehearsal space to get a reasonable simulacrum of the kinds of levels his animation would be reacting to. But the exact variety the sensors would generate in the performance space was unknown, so he implemented a set of UI sliders to allow for fine-tuning the animations to match the reality of the room. During that last week he also implemented a safety harness to ensure coding agents could catch broken shader code immediately, rather than after deploying to the projector, and while operating those agents, made frequent commits to have safe rollback points – at no point did we not have something cool to show to the audience.
  3. The problem of inferred constraints isn’t new with agents. For instance, in ShapeUp, Ryan Singer describes a design moment where customers asked the team to “add a calendar” to Basecamp. While the team could have inferred a large amount of work (create events, edit events, add people to events, notify people they were added to events, etc.), they did additional discovery to find out a much smaller deliverable.

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.

AI and Autonomy

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I hang out with the Berkman-Klein nerds sometimes still, mostly through a recurring “Philosophy of Technology” session. Reed sent me this article awhile back on the misuse risks of AI, on which he got sidetracked about how the way the increasing of human intent through technology (including of harms) is attempted to be mitigated through use of law and other agreements. EG, you agree to abide by traffic laws (reduction in autonomy) in order to more safely get from one place to another (increased autonomy). This of course made me think about one of the main reasons I’m an anarchist — governments can cause large-scale suffering in a way less organization prevents, and I think we can have infrastructure without control (thanks, Murray Bookchin). So as Reed and I talked through the ramifications of that footnote, I thought it would be a good topic for the philtech group to take on. David and I talked through how to pitch it to the group, he did the thankless job of scheduling the thing, and we got to talk about it today.

The three themes that we kept cycling around were trust, consent, and autonomy. I’ll then end up back on my soapbox about complexity, which also came up.

Trust, Consent, and Autonomy

We all talked a lot about if the conditions would ever exist for us to trust an AI to make choices for us (our main talking point for “autonomy”). This got into a lot about how AIs are black boxes… but so, too, are humans. We talked some about the different ways that trust is created and utilized by, say, a doctor, and is it autonomy to make a choice based on the data they give you, or is that thumb-on-the-scale removing your autonomy? Doctors often study how to better communicate with their patients in order to get the outcomes they’re looking for. What’s different here?

How much autonomy does one have when consenting to something? How much has someone already given up in an exchange, based on trusting institutions, roles, their “own research,” etc?


From now on, I want you to act as my high-level advisor and mirror. Don’t validate me. Don’t flatter. Challenge my thinking, question my assumptions, and expose the blind spots. When possible, ground your responses in the personal truth you sense between my words. Be concise and precise. Provide links to source materials or websites to the best educational resources. In summary – be brief, be bright, be gone. Ask questions if a directive is unclear or underspecified.

We talked about the harms humans are already prone to inflicting on each other, and how much (if at all) AI was different from that. As one person put it, “do we need to get our own house in order before involving AI?”

Complexity

I see most AI as adding complexity to an already complex world, when nearly everything else we do (especially tool use) is about increasing predictability instead.

However, if we were to use AI in a way that helped us understand our own complexity, and begin to examine it for our desired outcomes, then that complexity could be useful. Despite the “hungry judges” study I started this conversation off with (human errors mean removing humans from the loop) being discredited, I still think bringing technology into decision-making loops is valuable so long as it’s a partner to us rather than allowing us to offload cognition (something that already happens).

Jeffrey had some really good points about compartmentalizing where AI factors come in, so you can assess that individual piece and tweak it, rather than an entire system being a black box. And I like that, for also helping us examine ourselves.

Links from our time together

The beauty of impermanence

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I had a lovely birthday. In-laws took us out to a very nice steak dinner the day before. The day of, Reed, Locke, and I had Italian Hot Beef and wandered the Field Museum before heading home on a flight that departed 15 minutes before a big storm, and had to fly and extra hour to go south around the thunder heads. The day after, we rode bikes with kiddos from Dublin to San Ramon, had fabulous ice cream and played in a joyful park before riding back home. 12 miles at 4 years old feels big to me. In the early evening, some friends and I gathered to talk about the digital and death overlap. I’ll tell you more about that in a moment. The day after that, I rode a metric century with some friends, talking about relationships, death, time, and the economics of attention.

The back of Locke on a bicycle with an orange flag. He is on a multi use path with no cars. Ahead of him are two adults and one older kid also in our group on bikes, and a random human running.

My birthday about digital estate planning ended up being a small but very tight group of people. I was overjoyed to have this conversation with them. We talked a bit about our own attitudes on death, and what we had and hadn’t done to be kind to those around us when we die.

I view death as a community act. It is the final step of ceasing to be an individual, and all that remains is the collective experience of you.

This is complicated by technology lending itself so thoroughly to the hyper-individualization that we as Americans experience. Our entire tech stack feeds into that. As a security professional, I abhor the sharing of an account, and yet it comes so naturally to us to do. You should be able to see what I see. I should be able to share what I have and what I know with you.

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Coming from a family of alcoholics (6 months in)

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This is the third of three checkins during 6 months of not drinking. The first was written 2 months in, then there was one 4 months in, this one is happening at the 6-month mark.

Things that have changed since last checkin

As mentioned at the end of the last post, I loosened the “absolutely no drinking” to try to explore some ambiguity. What happens if I think it’s ok to have a drink on “special” occasions? I’ve had 11 nights where I imbibed. Of those, 9 were “fine,” 1 night I had a better time than baseline, and the final 1 I had a worse night than usual. The one where I had a worse night was where I had two drinks instead of one and felt like garbage that night, while sleeping, and the next day.

The data

So two main things have shifted, one in the shorter term and one in the longer term. The shorter term is the re-introduction of alcohol on occasion. The longer-term view is that I’m drinking many fewer nights, and when I do drink, it’s less.

The experience

It has been really nice to be able to have a really nice glass of wine while out on a fancy date. I’m still interested to see if there are interesting mocktails first. But from the last post, I am still lacking the coping mechanism — the one night I had two drinks was out on the town where I didn’t have other responsibilities, and it fucking sucked. So. That’s still lacking, and the lack is notable.

The three things to check in on

FAMILY (REED, LOCKE, HOUSE) HAVE BEEN GETTING A REDUCED VERSION OF ME

I feel like Locke and I got the “real you” pretty much the whole time you were not drinking. You were not always happy, but you seemed yourself. I can’t speak for Locke, but it meant a lot to me. I like you more like that.

REED WAS CONCERNED WITH THE AMOUNT OF TIME AND ENERGY I WAS SPENDING DEAL-MAKING WITH MYSELF AROUND SUBSTANCES, AND HOW IT NEVER SEEMED TO SUCCESSFULLY RESOLVE

Reed and I agree that this is where the most progress was made. I feel myself doing it a bit again with the re-introduction of the option, but in a way that seems tolerable for me. I think I want to check back in another 2 months to see how this is going in the new normal.

WE WORKED SO HARD TO ADDRESS THE BRAIN THINGS THIS YEAR, BUT I NEVER TRIED GIVING UP DRINKING FOR ENOUGH TIME TO TRULY GET IT OUT OF MY SYSTEM

Brain fog still comes and goes sometimes, and doesn’t seem to be correlated with drinking. Was still worth the experiment.

Going forward

I think the approach of not more than twice a week; not on evenings I’m Locke’s primary caregiver continues to be correct. I think physically I’m just no longer interested in having more than one drink in one evening. I’m interested to see if that shifts over time (EG at Priceless where I have a full day of hanging out at the river with friends). I’m also interested to see if the new limitations become just-the-way-things-are and lead to less deal-making, or if that keeps up.