Charter Houses


There are a lot of really big houses (6+ bedrooms) on the market for around a million dollars, or sometimes less. Like this three-story, seven-bedroom house just outside Albany, NY, which recently sold for $1,181,300. Or this ten-bedroom house just south of Boston, MA, which recently sold for $990,000. Or this eight-bedroom house in Cincinnati, OH, which recently sold for $455,000. Some of these places are old bed & breakfasts; some are intended as rental properties; some of them are just big. Some of them are FRICKIN MISSILE SILOS.

Big investments generate quite a lot of money — you can draw off about 4% of an investment every year without depleting the principal, because you get back that much or more in interest. Even if you did nothing but stick the money in an S&P 500 index fund, the historical average is about 10% per year. That’s not guaranteed, but it’s pretty damn good.

If we assume 4% annually, a $3 million endowment would generate $120,000 a year, or $10,000 a month indefinitely. A $2.5 million endowment would generate $100,000 a year, or $8333.33 a month. Even a measly $2 million endowment would generate $80,000 a year, or $6,666.66 a month. 

Hail Satan

Any of these amounts would be enough to purchase a big 6-to-10 bedroom house in many areas, with some endowment left to generate interest each month. If you sink $1 million of a $3 million endowment into a house, you still have the remaining interest from $2 million every month.

Once you’ve bought a house, you could use that interest to support a houseful of people. Exact numbers vary by location, but the interest should be enough to keep the house in good repair, pay property taxes, pay for utilities and internet access, feed everyone, buy a junky car, and even give them all a small stipend. 

The big gains are in rent — getting a decent room can easily cost you $1000 a month these days, so eight people seeking out individual lodgings would be in for $8000 a month collectively, or $96,000 a year! But if they all live in an 8-bedroom house with a mortgage of $3000, that’s only $36,000 a year, and you save $60,000 annually. (And if you purchase the house outright, then of course there’s no rent at all.) 

We could throw together a bunch of examples of different houses you could buy, in different places all around the country. Or we could just give you a link to the Charter Houseulator, and you can take it for a spin yourself! Find a nice 5+ bedroom house somewhere using Zillow (big houses in Nova Scotia are pleasantly affordable!) and plug in your best estimates for all the variables.

You’ll notice a few things. It’s clear that a mortgage is the wrong choice here. You won’t come out ahead until 30 years down the road when the mortgage is finally paid off. If you have the money, buy the house outright.

Healthcare is the big stumbling block — in a lot of scenarios, you just won’t have enough to pay for everyone’s insurance. Residents might qualify for some kind of reduced rates depending on income, but this seems to vary a lot by state.

Even in the best-case scenarios, it’s hard to end up with enough to give your residents much of a stipend. This still isn’t such a bad deal — they get their rent, their food, and maybe their health insurance all covered. They even get access to a junky car. What more could you want? 

vroom vroom

The situation improves a lot if you start with an endowment of more than $3 million, of course, or if you assume you can get more than 4% interest per year. But even within these constraints, you can get pretty decent living conditions for 5-8 people if you choose a house in the right place and give them a shitty enough car. Go ahead and mess around with the values in the Houseulator and find out!


Charter houses could be used to fill all sorts of weird niches.

Young People

Maybe you think college is a waste of time (and really who doesn’t these days). Or maybe you just think we should make it easy for young people to take big risks, and work on moonshot projects that will take years to pan out.

In that case, a charter house could be an accelerator for young people. Lots of high school or college graduates would love an opportunity to not think about paying rent and focus on their passion projects for the next several years. 

In general, young people don’t mind a slightly marginal existence, so this setup fits them pretty well. The average 30-year-old would have a hard time accepting a tiny stipend, even if rent was covered and there were no strings attached. The average 30-year-old also probably has better options, where they can make a lot more money, even if they have to work for it. But the average 22-year-old would jump at the opportunity to [checks notes] get paid to not pay rent, and most 22-year-olds don’t have access to a better deal than this. This is even more true for the average 18-year-old, especially one that doesn’t want to bother with college. 

Young people! Never going to amount to anything am I right?

You might be concerned that young people would like their charter house so much they would stay forever, but this is where the very small stipend becomes an advantage. From the ages of 18 to 24 or so, survival alone is pretty enticing. But as they grow up, most of your residents will begin to dream of more than a $500 a month stipend and free rent. Soon they will hunger for more space, or nicer equipment, or a car that doesn’t have holes in the floor. They’ll find a job or some other way of making money and graduate, moving out on their own. If some of them do decide to become long-haulers, that’s ok too, since it gives your house more institutional memory.

This level of security helps people figure out their comparative advantage, and lets them found more small businesses and startups, because they don’t need to make the same kind of money right out of school. Obviously that’s good for innovation.

Research and Scholarship

Here’s a question: what’s the minimum form of scholarly institution? Existing universities are huge, but every university is made up of schools and departments, and in many cases these function almost as independent entities. How small can you go and still call it an institution? 

A charter house could be an interesting experiment in marginal scholarship. Charter houses could serve as a replacement for academic departments, possibly with a mentoring component (e.g. half of the residents are students, with mandatory turnover after a couple years). You buy a house and give it an endowment, and recruit a bunch of biologists or linguists or computer scientists, and see what kind of scholarship they produce. We don’t know if it will be good, but we’re sure it will be different.

The kind of biologists who would show up to live in an abandoned church in Oak Creek, Wisconsin or an old Victorian mansion in Normal, Indiana would be a very different kind of biologist than the kind who would take an academic job at your local university. But we think this is an advantage.

The Manhattan Project

Extrainstitutional Support

There’s an ongoing conversation about how we as a society can support people who have important but hard-to-compensate roles (see for example this twitter thread). There are lots of roles, especially in open source software but also in other areas, where the work is critical but no one is willing to pony up to pay for it.

These roles don’t fit within normal funding structures — they’re too small for a business to hire the person on, too small to form a nonprofit around them, and too big to be supported through individual donations. And beyond this, there are even more projects that someone should do, and which might attract support retrospectively, but no business or nonprofit would be willing to support prospectively.

Charter houses could solve this problem neatly. A charter house or two could easily be set up with positions offered to people who are filling these roles, providing them with a minimum of support — at the very least, free rent and free high-speed internet. These people are professionals, so this may not be enough for them — but there’s no reason they can’t get support from the charter house and make additional money in other ways. They can supplement that support by consulting, getting a real job, being a bounty hunter, etc. 

In fact, since people in this position might also have a part-time consulting gig or something, a charter house targeted at them might be able to survive on a much smaller endowment, only paying for their rent, and not covering their food and healthcare, for example. 

There are a lot of projects that would have no prospective support because they’re super high risk. But if we have an ecosystem for encouraging lots of high risk projects, we will eventually get a lot of crazy successful moonshots. Our society already does this a bit for open source software — we should do it for other important avenues of progress as well. Like apenwarr says: “The best part of free software is it sometimes produces stuff you never would have been willing to pay to develop (Linux), and sometimes at quality levels too high to be rational for the market to provide (sqlite).”

Unprincipled Mixture

You could also allow a totally unprincipled combination of all of these approaches, and we think that would work pretty damn well. It’s fine if you have three engineers working on a startup on the ground floor, an essayist sharing a bunk bed with a painter in a room above the garage, and two biologists in the attic. 

A mix of approaches is good and healthy. If you fill a house with biologists, they will all be competing with each other. They may even end up at each other’s throats — they are too similar. But mix in a little diversity, a few chemists and physicists, some experts in East Asian literature, and a Turkish math wiz who speaks almost no English, and things will work very well indeed.

It’s tempting to make each charter house alike in scope and subject — one house for the college dropouts, one house for the physicists, one house for the painters, one house for the startup accelerator, one house for the mystics, etc. But siloing people in this way is going to be counterproductive. Young people will benefit from sitting across the dinner table from old people; old people from young people. Biologists will benefit from playing video games in the living room with art historians. Philosophers will benefit from going grocery shopping with blacksmiths. Electrical engineers will benefit from fixing windows with clowns. Bartenders will benefit from cooking dinner with astronomers.

From Left: Child, Wizard, Hatter/Grandma. Not pictured: Fire Demon, Turnip

As Paul Graham says in his essay Hackers and Painters, “I’ve found that the best sources of ideas are not the other fields that have the word ‘computer’ in their names, but the other fields inhabited by makers. Painting has been a much richer source of ideas than the theory of computation.” 

So it’s ok, even ideal, to have a charter house where most of the residents are college dropouts, and there’s one 60-year-old living in the basement maintaining ‘runk’.


Charter houses capture a number of features of other successful programs.

They’re kind of like the Alaska Fellows Program. In this program, you stick a bunch of recent college grads in a house somewhere in Alaska, where they live together for about a year. Housing and utilities are covered, and everyone gets a monthly stipend of $1000 on top of that. We hear it works great. If young people sign up for this, you can bet they would also sign up for a program with more freedom and where they didn’t have to live through the polar night.

They’re also kind of like medieval guilds. A guild was an organization devoted to a specific kind of skill, one with practical applications, and that saw to training and organization. They pooled funds and sometimes shared tools or workshops. The first universities started out as guilds of students, who banded together to hire tutors (the first professors) and for mutual protection. Other medieval examples include various religious orders, like the Franciscans or the Poor Clares. In these particular examples you personally owned no property, but you still had a place to stay. Religious orders often owned buildings (monasteries, convents, abbeys, etc.) and conducted various forms of scholarly work together. Gregor Mendel, the father of genetics, was an Augustinian friar and abbot. 

Something like charter houses already exists during college. Particular dorms will have a particular theme, or a subset of all the people in a club or frat will live together. When people graduate from college, it’s pretty common for them to share an apartment with friends for a couple years. It’s clear that people enjoy living together like this, as long as they get their own space.

This is pretty good evidence that, given the option, young people would try living in a charter house. And it seems like this is just straight-up competitive with college in almost every way. You have to pay for your housing in college, but in Soviet Russia, house pays you a charter house pays you. In most colleges you have to share a tiny, cramped room with other people, but most charter houses would be big enough for everyone to have their own room. In college you have to study some predetermined topic and take classes, but in a charter house you can spend your time on projects that actually teach you what you need to know. In college you have to hide your drugs, but in a charter house, the chemist who lives in the walk-in closet is synthesizing LSD in the bathtub.

An example of a similar successful model is Hampshire College in Amherst, Massachusetts. At Hampshire, upperclassmen don’t live in dorms, they live in mods (“modular housing”) of 6-10 students, which are like medium-size apartment buildings. The mods are big — almost everyone gets a single, and the few doubles are huge. And you can work on whatever you think is important because of the traditional Hampshire package of no majors, no tests, and no grades (yes, really!). The only downside is that you still have to pay, but charter houses fixes this. And we know this crazy system works — Hampshire has produced alumni like Ken Burns, Elliott Smith, Lupita Nyong’o, and Eugene Mirman, the man who voices Gene on Bob’s Burgers and deliverer of the best commencement speech of all time

Ken Burns does an in-depth profile of fellow Hampshire alum Eugene Mirman  

The benefit of college is of course the fact that it’s large — there are lots of people you already have something in common with, which makes it easier to build community and a strong social network. A single charter house can’t compete with that, but if you put a bunch of houses in the same town, they can support each other in various ways.

We’re not just talking about community — they can share skills and resources. The charter house full of musicians is the only house with a grand piano, but residents of the other charter houses can visit to use it. The chemists sprang for a projector or a giant TV, so everyone comes to their place for movie nights. The videographers living in the garret of the old B&B help record the experiments the electrical engineers are doing in the charter house down the street, and put it all on YouTube.

Replicating the benefits of college without the headaches isn’t just for college-age kids. Most people who went to college don’t miss the exams or the food, but a lot of them miss the sense of community and the ability to casually hang out with interesting people. Charter houses could be designed to be attractive to almost any age group.


We’re not financial advisors, so we can’t advise on how to set up the institution behind a charter house. But we can advise a little on how we think you should organize it. 

In brief, we think a charter house should have very few rules. 

Certainly you do want some rules. You probably want to have one resident who is on all the paperwork, who can collect the interest from the endowment every month, and who is responsible for paying all the bills. You want some legal firm or something to oversee the endowment. You want rules about what happens if the endowment grossly underperforms or overperforms — what happens to a house if their $2 million endowment shrinks to $1 million, or grows to $4 million? You want rules about what happens if the house ends up being abandoned. 

(A growth rate of 4% per year does seem pretty conservative, so we support a rule that if a charter house’s endowment gets too big — if it ever reaches double the original endowment, if it breaks $5 million, something like that — it should be forced to split in half and spin off a sister house nearby.)

Other than that, we don’t think you want many rules at all.

There are many rules that do seem enticing at first glance. If your charter house is intended for biologists, you might want to make a rule that only biologists can live there. If your charter house is meant to be an accelerator for young people, you might want a rule that no one over 26 can live there. You might want a rule that no one can live there for more than 4 years, to encourage turnover and give lots of people a chance to live in the house. If the house itself has only eight rooms, you might want to make a rule that no more than 10 people can live there at a time. You might want to make sure at least a few people are living in the house at all times. Maybe you want to make a rule, “no girlfriends/boyfriends”, or at least “no families/kids”. And you would probably want some rule about how people are chosen to join the house.

We have only one rule in this house: don’t leave the window open.

These seem like good ideas, but we are against them for a simple reason: they are really hard to enforce. Who is going to go check that everyone living in the house is a biologist? If the guy playing guitar in the living room says “no I’m a biologist”, what are you going to do? If you try to enforce a maximum number of residents, how will you tell who is living there and who is just visiting? How long can someone visit for, before they count as living in the house? A week? A month? 

So our recommendation is, don’t make these rules and don’t waste time and effort on trying to enforce them. It’s fine to tell a house, “I set this up for chemists” or “this house is to support open software” or “I want to support young people, so try to graduate when you can.” But don’t try to enforce these rules — trying to enforce them will just lead to internal squabbles. 

Let the residents have friends over. Let them stay as long as they need. Let them decide how they’re going to pick their housemates. And let them learn to govern themselves. This teaches them that 1) they are capable of self governance and 2) specific tips and tricks on how to actually run a small organization/government. Pretty pro-democracy. 

So we think charter houses should have as few rules as possible. On the other hand, they should definitely have traditions. Each house should have a name, house colors, maybe a crest. A motto if they can come up with one (maybe, “I am a beautiful animal! I am a destroyer of worlds!”). Perhaps an official song or chant. Traditions like a house movie (may we suggest WPDR) or a monthly poetry contest. And of course, a party every year on the day it was founded.

You can speculate and plan all you want, but you won’t know what works and what doesn’t until you give it a go. You really want someone to try it, to start some charter houses and see what they come up with, what problems they run into, and what solutions. 

You want to invite the people who will live in the house to be your co-conspirators. If you make up a bunch of rules, even good ones, and try to enforce them, your residents will resent you. But if you bring them on board, and let them tinker with it, they will surprise you.

“Let yourself be second guessed,” says Paul Graham. “When you make any tool, people use it in ways you didn’t intend, and this is especially true of a highly articulated tool like a programming language. Many a hacker will want to tweak your semantic model in a way that you never imagined. I say, let them; give the programmer access to as much internal stuff as you can without endangering runtime systems like the garbage collector.”

We feel the same way — let them get at everything except the metaphorical runtime systems. In hacking they call this the “Hands-On Imperative”, and while actual code may or may not be involved, the charter house is more than a bit of a hacking project. “Hackers can do almost anything and be a hacker,” said Burrell Smith, the designer of the Macintosh computer, at the first Hacker Conference. “You can be a hacker carpenter. It’s not necessarily high tech. I think it has to do with craftsmanship and caring about what you’re doing.”

You want these houses to be very different, and you want to use the power of evolution. Lack of diversity is so bad that in biology, they call it genetic erosion.

You want “speciation” — you want to release ideas into the world and get feedback from their success and failure. We’re going to continue with the Paul Graham quotes for a second, because charter houses are more than a little like a combination of startups and startup accelerators. “If you release a crude version 1 then iterate,” he says, “your solution can benefit from the imagination of nature, which, as Feynman pointed out, is more powerful than your own.”


Most plans to change the world require a lot of coordination. You have to argue with senators and NGOs and the university PR department, on and on and on. But anyone who can spare a few million dollars can set up a charter house unilaterally.

Haha yes, “spare a few million dollars”, you laugh, but donations like this are made to nonprofits and universities all the time. We don’t want to take food out of the mouths of hungry children, but let’s just say that some of these donations are more inspiring than others. Like the $250 million gift from Charles B. Johnson to Yale in 2013. Or the $350 million gift from Michael Bloomberg to Johns Hopkins in 2013. Or the $400 million gift from John Paulson to Harvard in 2015.

We’re not even necessarily talking about bringing in new money — you could do a lot just by redirecting donations that are already being made. If Bloomberg wants to give several hundred million dollars to Johns Hopkins (estimated endowment: $8.8 billion), who are we to judge? But in a world where we can’t seem to stop talking about stagnation and academic decline, doesn’t it seem worth it to try a different model? How about you spend $10 million to set up three charter houses with endowments of $3.3 million each, and give Johns Hopkins a mere $340 million? Or set up ten charter houses with endowments of $5 million each, and see if Johns Hopkins can survive on $300 million?

Exhibit One: A real charity case

What’s gonna give you more bang for your buck, giving Stanford a shiny new engineering building and filling it with smartboards and swivel chairs and all of the engineering students who would have gone to Stanford whether it had a shiny new engineering building or not, or giving some of those engineers a house where they can work on stuff they think is cool, and enough food to keep them alive while they do it?

Another thing: those engineering students will take on like a hundred thousand dollars in debt if they go to Stanford! An advantage of charter houses is that nobody has to take out a loan.

So instead of giving $20 million to an institution that you are certain will muddle on in acceptable mediocrity, split that money up among several charter houses. Some will fizzle out; a couple may even explode. But others will become self-sustaining little critters that will spark and wriggle and lay plans of their own.

Newsletter Natural Selection

Apparently, Substack wants to destroy newspapers. And maybe that would be good — maybe it would be good for journalism to be democratized, for bloggers to inherit the earth. Of course we’re bloggers and not newspapers, so maybe we’re biased.

Obviously it would be great if someone came up with a set of blogging and newsletter tools that were just amazing, that were the clear front-runner, that outperformed every other platform. We’d love it if the technical problems were all solved and we just had a perfect set of blogging tools.

But if everyone ends up on the same platform, well, that’s kind of dangerous. If one company controls the whole news & blogging industry, they can blacklist whoever they want, and can squeeze users as much as they want.

Even if you think Substack has a good track record, there’s no way they can guarantee that they won’t squeeze their writers once they control the market. Even if you trust the current management, at some point they will all retire, or all die, or the company will be bought by, and then you’re shit outta luck.

Substack just can’t make a credible commitment that makes it impossible for them to abuse their power if they get a monopoly. You have to take them at their word. But since management can change, you can’t even really do that. They just can’t bind their hands convincingly.

But there may be some very unusual business models that would fix this problem. 

On the Origin of Substacks

Imagine there’s a “Substack” company that commits itself to breaking in half every time it gets 100,000 users (or something), creating two child companies. Each company ends up with 50,000 users. All the blogs with even-numbered IDs go to Substack A, and all the blogs with odd-numbered IDs go to Substack B. The staff gets split among these two companies, and half of them move to a new office. Both companies retain the same policy of breaking in half once they hit that milestone again — an inherited, auto-trust-busting mechanism.

(Splitting into exactly two companies wouldn’t have to be a part of the commitment. They could equally choose to break up into Substack Red, Substack Blue, and Substack Yellow: Special Pikachu Edition.)

In addition, a core part of the product would be high-quality, deeply integrated tools to switch from one of these branches to another. Probably this would involve an easy way to export all your posts and a list of your subscribers to some neutral file format (maybe a folder full of markdown, css, and csv files), and to import them from the same format into a new blog. If you end up in Substack B and you want to be in Substack A instead (your favorite developer works there or something), the product would make it very easy to switch, maybe to the point of being able to switch at the push of a button.

To help with this, the third and final commitment of the company, and all child companies, would be to keep the software open-source. Unlike biological evolution, software evolution isn’t siloed. If Substack Air implements a great feature, and the team over at Substack Earth likes it too, they can just go to the open-source code of their sister company, snip that AAAGTCTGAC, and copy it over to their branch.

Each of these child companies would go on to develop their tool from the same starting point, but of course the companies would speciate over time. More competitive branches would get to 100,000 users first and would split again, so there would be more descendants of successful branches. Bad branches would die off or just never grow enough to speciate. 

Because it’s easy to switch, branches that make a bad decision will also face an exodus of users to different branches that don’t suck. Of course, one species of Substack might choose to remove the feature that allows you to switch easily, but this seems like evolutionary suicide. Faced with the prospect of being locked in, most users will switch away if there’s any hint of removing this feature. It’s ok if people decide to stay, of course, things might just get weird.

After several generations of isolation from the main line, bloggers will look like this.

Many branches would die — nature is red in tooth and claw, after all — but many companies die off in the normal course of the economy anyways. And it’s reassuring that there would be an ecosystem of similar, related companies that would be ready to hire on any deserving refugees.

Ghosts Undergoing Mitosis

This would keep one company from taking over the blogging ecosystem and imposing terrible conditions. Or rather, if one lineage did dominate the blogging ecosystem, that could be a good thing, not a danger to free thought and free expression. That lineage would be split up across multiple companies with different leadership styles and different values, and would lack the kind of monopoly that tempts men to evil.

If Substack were our company, we would not only implement this idea, we would emphasize it a lot in our marketing and recruitment — not least because your target demo, bloggers, are smart and paranoid. They want this kind of freedom, ownership, and control, and they’re worried about the fact that current platforms sometimes seem a little power-hungry.

It would take Substack a minute to make this pivot, but other companies could do it right now. In fact, the web publishing platform Ghost is already planning to do something along these lines.

Ghost is already open-source, which is the big requirement to get started immediately. If they developed some quality Ghost-to-Ghost migration tools (uhhh… G2G tools?) and started branching, they could do this tomorrow. But probably they don’t want to follow our plan, for in an amusing display of convergent evolution, they have come up with a very similar plan of their own: they plan to stop growing at 50 employees and let other companies take on the growth from there.

(For more about Ghost’s fascinating business model, see here.) 

John O’Nolan, the founder of Ghost, who apparently lives on a sailboat (mad props) was interviewed by the Indie Hackers Podcast, where he said (go to 41:49 or so):

Interviewer: I think with you, we were just talking about this, I think, a few months ago, you have this other arbitrary constraint, I’m not sure why you have it, it might be like a side effect of the fact that you’re a nonprofit, but you can’t hire more than fifty people, was it? At which point you’re constrained and you have to figure out how to grow and become bigger and better without hiring a single more person than fifty. So where’s that constraint come from? 

John: I love that you brought this up, because it’s something I think more and more about nowadays. We’re coming up on, I think 27 people, so more than halfway there, and the rate at which we’re hiring is increasing, so the kind of fifty-sixty number is very much on the horizon, it’s within sight. And the constraint comes from, I have never worked at a company bigger than that which didn’t have office politics, or disconnection from the mission, or where things kind of stopped being fun. And from all the people we’ve hired over the years, there’s a remarkable amount of refugees, who were ar startups, they passed the kind of sixty, seventy person mark, things stopped being fun, middle management came in, the founders sort of left the early team behind, and started pursuing growth goals at the cost of people, and everything just sort of like *sigh* lost what made the journey special, around about that point. 

And there are just so many people who have the exact same story, at a certain point we just said, ok, well, what if we just don’t grow bigger than that, we’ll just stick like not bigger than fifty-ish. Fifty, sixty, somewhere around there. Not going to like, say, be really belligerent about a fixed number, but around that point, what if we just put a line, say, “ok no more”. And… what will that do? 

So, first of all, the same as what I was talking about earlier, it keeps Ghost as a company I’m happy to be stuck with. I want to have a group of fifty or sixty people where I know every single person well — not a large group of strangers who are all just working to a common economic incentive, but a team, a group of people who really know each other deeply and meaningfully, which I think you can still achieve around that size. 

But then, the logical question that follows is, ok, what are the goals of the company once you have fifty or sixty people and you still have ambition? How do you fulfill whatever goals you have that kind of don’t fit into the model of that size of company? And the answer is, you have to change your ambition, or you have to change the model with which you approach your goals.

So, a lot of how I think about Ghost now is less about growing one company — one centralized company — and more about growing a large, decentralized ecosystem. So whereas many-slash-most companies will try to grow bigger, and absorb smaller companies, and kind of be this big blob, consuming more and more of the market to become the holy grail of what everyone wants to become, which is a monopoly that dominates a market, kind of think about the opposite, how can we make Ghost, the products, a really strong and stable core, and then spin off all the other things for which there is demand from the market, but that we don’t have a big enough team to build. 

So maybe that’s community features, or maybe it’s video and media that integrates with Ghost really well, or maybe there’s an enterprise hosting option of people who DO love to get those emails from large companies with a big procurement process and close those deals. If we can have our smaller team make a tight core that enables lots of businesses to exist around Ghost, and around that open-source core, then an ecosystem will evolve around it of multiple economic dependents, and it will probably function similarly to a large company, except that I won’t control all of it, and that’s actually very appealing to me, I don’t want to control all of it, I don’t want to have the final say in how everything should evolve. 

This sounds a lot like the speciation idea we describe above. He even uses the term “ecosystem”! 

There are a few core differences. Limiting the company by the number of employees rather than the number of users might be the better way to go. So in a different version of our proposal, the company could be organized into several teams and the teams could become separate companies once the company has hit 60 employees or something. 

O’Nolan envisions an ecosystem more like Darwin’s finches — related companies that spread out to fill different niches, one for blogging, one for comments, one for video, one for different hosting models, etc. This seems like it would be relatively easy to do, and you can see how a successful company would draw related companies into existence, like a coral reef.

In contrast, we imagine an ecosystem of different companies competing (hopefully friendly competition, but still competition) for the same major niche, like birds and mice all competing for the same nuts and seeds. This seems good because competition will lead to better products, especially given built-in features that let bloggers vote with their feet. It also seems uniquely good in that, if Ghost or Substack or anyone does come to dominate the blogging world, this system will keep them from monopolizing it. 

So we think Ghost should consider not stopping at 50 employees, but undergoing mitosis instead, and splitting into Ghost Day and Ghost Night; or Ghost Sweet and Ghost Sour; or Ghost To and Ghost Fro; or Ghost Claw and Ghost Fang; or Ghost Sound and Ghost Fury; or Ghost Charm and Ghost Strange; or Ghost Video and Ghost Radio; or Ghost Milk and Ghost Honey; or Ghost Rosencrantz and Ghost Guildenstern; or Ghost Migi and Ghost Hidari; or Ghost Ale and Ghost Lager (and Ghost Lambic); or X-Mas Ghosts Past, Present, and Future; or 

*cane reaches out from the wings and pulls us off stage*

Special thanks to our friend Uri Bram for enlightening discussions about the world of online publishing.

TODOs from Paper Systems

I want to start by talking about the emotional experience of working with a todo list. 

The biggest hurdle todo faces is that the emotion you generally experience when you look at your todo list is shame. This is bad because it makes you uncomfortable with the tool and makes you want to avoid it — you don’t want to look at it because engaging with it makes you feel bad, so you don’t use it, or you wait until it’s too late, you avoid it, etc. etc. 

The key to fixing this is coming up with a todo system where the emotional experience is pride. This way you often want to look at your todo list, you enjoy the experience of working with it, you approach it, you seek it out, etc.

To help describe ways we can do this, I’m going to go over some of the pen-and-paper todo systems I’ve used and describe how I think they fulfill the goal of making the emotional experience of working with your todo list one of pride rather than of shame.

Example #1: Digital Painting Calendar

Back in 2017, I was trying to learn digital painting. I was enjoying keeping up with it, and so I set myself a soft goal for myself of trying to do some digital painting (even if only 10 minutes) almost every day.

To keep track of this, I printed out a single-page calendar for the year, and simply marked off every day where I did some digital painting. By the end of the year, I was so proud of this that I saved an image of the calendar, reproduced below. I think I have the hard copy somewhere, even. This was such a positive experience that looking at it STILL makes me proud, even years later: 

Why did this work so well? I think there are a couple reasons.

First of all, the goal was low-commitment (any painting at all). This encouraged me to start painting often, and 10 minutes often turned into 3 hours. But this is a feature of the goal, not the todo system.

The goal was also simple. This helped the todo system, because it made it very easy to determine whether I had “earned” the right to check off each day. 

The scope of this todo system also has some great features. Because the scope is a year long, as soon as I missed one day, I knew that there wasn’t a chance of me getting 100% on the full year, which made it feel lower-stakes, while still being important. Early failures made the stakes not feel catastrophic, which decreased the threat and sense of shame. Incidentally, I think this is a strong argument against the use of daily streaks in todo apps. Streaks are a threat, not encouragement.

The calendar is also naturally split up into sub-units. There are 12 months and about 52 weeks. This means each week and month could also stand alone for success (or failure), keeping the local stakes high enough to be engaging while still avoiding feeling catastrophic. You’ll see that I completed several weeks perfectly. I also tried (and failed) to do every day in April, then tried (and succeeded) to do every day in October. Having these “local stakes” increased the chances for feeling proud of an accomplishment while keeping the total stakes low in terms of failure. I feel good that I 100%’ed October, but I don’t feel bad at all that I missed a bunch of days in December.

I also think this system works well because it covers just ONE of the tasks that I had on my mind then. I did other things in 2017, but this document doesn’t even try to cover those aspects of my life. I wasn’t overwhelmed when looking at it, and it forms a nice historical document that isn’t cluttered by unnecessary context.

Finally, I think this system works well because it pushes back against what I’ll call “the Tetris Problem”. This is something we will come back to again and again. Namely, the Tetris Problem is:

In this todo system, however, both errors and accomplishments are equally and fairly presented. There’s also some value in the fact that they are presented as fact (did I do painting this day or not), rather than as a judgment.

Robert Caro’s “Planning Calendar,” 1971. He shoots for 1,000 words a day — each day is marked with how many words he wrote with excuses in parentheses. (“Lazy,” “sick,” etc.). Source 

Example #2: Trello

I mostly don’t like Trello, but one thing it gets right is the combo of cards and checklists. 

When you have a checklist of 10 things, as you burn through it, the checklist fills up. One day 3/10, then 5/10, then 9/10. When you hit 10/10, it gets bold or changes color or something, I don’t remember. 

The important thing is that this turns Tetris on its head. In this system, accomplishments pile up, and errors are nowhere to be seen. 

Another nice feature is that accomplishments pile up at multiple levels. Completed checkboxes pile up in a list. Completed lists pile up in a card. Then, when the card is all finished, you get a final rush when you drag it to the “completed” pile. 

Importantly, the accomplishments don’t disappear until you manually choose to put them behind you. This is a critical difference from Tetris! With Trello, you bask in your accomplishments for as long as you want — until you say, “this was good but I’m ready to put this chapter of my life behind me, let’s move on to some new projects!”

Though this makes me wonder, should a system have a “trophy case” rather than a “completed” deck? A good point of comparison might be the “run complete” screens from recent hit video game Hades. Every time you successfully escape from hell, the game shows you a bunch of stats about your last run and you can bask in the success as long as you want. This seems like a nice feature.

(Not one of our runs)

Example #2.5: Trello Mimic on Paper

I copied this approach a little back when I was teaching, except I used a pen-and-paper approach rather than Trello. 

Unfortunately I don’t have pictures, but the general idea was this. I pinned a 8.5 x 11 piece of paper to the wall in front of my desk, where I could easily see it every day. Then, what I did is I scoped out all my teaching duties for the semester in a bunch of vertical checklists. I don’t remember the exact numbers, but something like, there were 12 weeks of lectures, 5 major assignments, 3 exams, etc. Each got a checkbox, and as I hit each milestone, I would check it off — one week down, one exam graded, etc.

This wasn’t quite as exciting as Trello for some reason. It didn’t make me feel proud, but it certainly didn’t make me feel shame. I didn’t have any problem looking at that list, and it gave me a good sense of progress as I slogged through some of the dumb-ass grading they made me do lol. I think I would have liked it more if I had felt better about the classes at [SCHOOL REDACTED], but I did not!

I notice that like the digital painting calendar, the scope of this was pretty long-term. I think that is part of what I mean when I focus on accomplishments piling up — it’s not enough for them to just pile up, they need to stick around for a while. It’s also useful if accomplishments produce ephemera, like the calendar, or like these checklists.

A semester may not even be a long enough scope! As a teenager, I mostly thought about tasks in terms of weeks and quarters. When you’re young, your life is explicitly structured around these short-term horizons. But as an adult, I am already starting to think about progress in terms of years, even decades. 

Compare also to the traffic stats interface provided by WordPress for this here blog. Normally we look at traffic per day, but we can immediately zoom out to look at weeks, months (seen below), or even years at the click of a button. With this, we can appreciate a greater scope whenever we want, and it can be nice to see how far we’ve come.

Example #3: Post-its in College

A long-term sense of accomplishment is important, but when we talk about todo, we also need day-to-day elements.

The best todo system I ever used in my life was in college. At the beginning of every week, I took seven post-it notes, one for each day, and wrote out my major milestones for that week. As I went through the week, I would check each off in turn, adding and removing tasks as needed. 

I don’t have any photos, but here’s an artist’s impression: 

At the end of the week, I would pull all seven off the wall and replace them, which was always incredibly satisfying. I felt like I had slaughtered the week every time. 

I do worry that a digital system will never be as satisfying as physically checking boxes and peeling post-its off my dorm room walls. But Trello for all its failings did give me some of that, so I’m optimistic. Probably the thing to do here is to look to the world of game design, to the concepts of game feel, AKA “juice”. Need that screen shake on my checkboxes!!! 😛 

If this system was so great, why don’t I still do it today? Strangely enough, I think it comes down to a few simple factors. In college, I always had only one desk, which was in my room. Ever since then, I’ve generally had one home desk and one work desk, and even that small amount of separation is enough to kill this system. In college, my desk always faced a blank white wall, perfect for hanging post-its. These days, my desk generally faces a window, to reduce eye strain. Trade-offs, man!

There’s also the fact that, when most of my todos were clearly tied to classes and student groups, it was easier to plan a whole week in advance. These days, my schedule is actually a bit too flexible.

Either way, this was a great system and I think there are a lot of lessons here.

The first thing you’ll notice is that, as before, accomplishments pile up. Every week, I knew what I had accomplished so far that week. Even if I missed a task on Monday, if I managed to get to it on Tuesday, I could go back and check it off Monday’s list.

Planning for the week helped keep me from carrying a todo from day to day. These days I still use post-its, but only one at a time. If I don’t finish a task today, I add it to the post-it for the next day. But this is a bad habit, and stressful too. It encourages me to carry many tasks in my working memory (and/or the paper equivalent), rather than spacing them out across seven post-its.

With the old system, I would have put the task at the point in the week when I thought I would be able to accomplish it. I didn’t get to it that day (which did happen sometimes), I would be able to see that it was overdue. This helped give it a naturally higher priority, and made for a clear indicator of just how overdue it was.

It also helped conflate personal and professional accomplishments. Now you may say, why would I want to conflate these? Isn’t it better to treat them differently? Well, I worry that too many people try to keep their work and their personal accomplishments separate, when both are controlled by the same limited resource — time. Having “get groceries” on the same list as “finish term paper” was a nice structural acknowledgement of the fact that both tasks trade on the same resource. I think it kept me from feeling bad when I didn’t get any “work” done in a given day. Hey, those personal chores were important! They were on the list!

It also helped that post-its are small. This reflects the limited time in a day and kept my ambition focused. I could only ever list a few tasks, so I figured out what I really needed to finish each day. It encouraged me to break up big projects into reasonable pieces, each only a couple of hours long, so I could check off a piece of the project on a given day. 

There’s another element which is also critical, but harder to explain. Nonetheless, I strongly believe it to be true. Having these limited post-its encouraged me to 1) do everything on my list as soon as possible, and 2) filled me with energy and a feeling of freedom afterwards. The same experience is described by Sasha Chapin:

And echoed in the responses: 

Whatever the reason, this is definitely a real phenomenon. In college, I churned through my requirements with astonishing speed — and then continued working really hard at whatever I was interested in.

This may have something to do with what Scott Alexander has called infinite debt (see also here). Your school/work/personal/whatever obligations — your schedule obligations — are in some sense infinite. You can always come up with new things to do. Like the moral equivalent, this can make your todo list feel really bad and overwhelming. This makes for bad designs — you don’t want to look at your todo list and feel like “your work will never be done, you’ll never be good enough.” Ouch.

In contrast, by scheduling finite goals for each day, you can give yourself the sense of being on track — not discharging all of your schedule debt, but discharging all your schedule debt for that day. After that point, you’re free for the rest of the day! 

This works even better with my post-its-for-the-week approach. By scheduling out the major milestones for the week, when you finish your tasks for a day, you’re not just on track for the day, you’re on track for the week! 

This can even give rise to a feeling that is so powerful and vicious I can only describe it as “bloodthirsty”. Since your schedule debt is effectively infinite, you normally have no chance of catching up, let alone getting ahead. Scheduling out the day is better because you can catch up and be on track, but you still can’t get ahead. But if you mark out your milestones for the week, you can actually get ahead of schedule. If you finish your work for the day, and you feel energized (which you often will!), you can get that bloodthirst and chew through the tasks for later in the week! That makes you feel more accomplished, and it also gives you more free time later in the week, leading you to get even further ahead — it’s a positive feedback loop! 

The trick here is making each day’s set of tasks accomplishable in the 24 hours you have. But you should be doing that already. If you do this right, you feel great, you’re more productive than ever, and you get “bonus time”!

Example #4: The Modern Hybrid

Right now I am using something that is kind of like the pen-and-paper Trello checklist approach described above, but I’ve added a few features that I think are important. 

This fills a different niche from the post-its (and you could probably use both). Rather than daily organization, this is the near-term scope of 1-3 months or so. 

There are two-long running goals I’ve had for my todo organization, which I’ve struggled with, but I think these todo lists are starting to approach it nicely.

The first I’ll call “families”. This is simply a recognition that, while all tasks trade on time, different tasks belong to different classes or families. You have your personal list, your chores list, your work list, your hobby list, etc. Personally I find it very disorienting if I don’t keep track of which task goes in which family — or worse, if I don’t know how many families of tasks I have going on at all! This makes my todo list feel infinite, and as we covered before, infinite bad! 

So on the subject of families, you’ll see that my checkboxes are broken up into different sections, so I know how many families I have and what task belongs to which. I think any todo list worth its salt will break things up visually — possibly by color or shape, but even better is to be broken up spatially.

My ideal software would let me slide around tasks and families on the page much like I do when laying it out with pen and paper. This is another thing Trello approaches with its spatial organization, but you could certainly go a step or two further.

Two examples

Families also serve my second goal, which is a clear representation of dependencies. Tasks within a family often have a clear priority structure and sometimes even have literal dependencies, where one thing has to come before another. 

I’ve always really wanted a good way of representing dependencies, but actual graphs/connections and so on never worked for me. But in this notebook system, simple layout alone seems to work pretty well. In my first two passes (above), dependency is roughly indicated by a combination of left-to-right and top-to-bottom, like English reading direction. Things lower on the page and further to the right are generally lower priority and/or depend on things above and to the left of them.

Below is my most recent version, which instead uses top-to-bottom alone to indicate dependency. Each column is a family, and vertical order approximately indicates priority and dependency, with items higher in the list being higher priority and being requirements for lower items. 

I say “approximately” because it turns out, you don’t always need to indicate dependency explicitly. A todo list is a memory aid, not a memory replacement. I can remember what the dependencies are — the vertical organization just makes it easy for me to think about it, compare across families, not worry about tasks I haven’t reached yet, and so on. 

Having a quick visual shorthand for dependencies is useful and saves time. Actually bothering to map out all the dependencies tends to look cluttered, and does not save time at all.

In conclusion:

To make you feel pride rather than stress or shame, the ideal features of a todo system are something like:

  1. Accomplishments accumulate
  2. Long-term scope to see the arc of your success
  3. Multiple levels of scope to get sense of reward at multiple scales
  4. Recognize that tasks and events all compete for one resource — time 
  5. Limit your daily tasks and get “Bonus Time”
  6. Clear visual families & dependencies, probably through spatial organization