The Letter Circle

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A thought that has been stewing for a while is “What is a form of social media I’d be willing to use?” So here is one app design that attempts to answer the question. It helps folks create and manage small social groups focused on thoughtful writings and conversation. 

The joy of letter writing

At one point, there were long form letters exchanged between experts in their field. Artists and writers would write to one another and share their latest struggles. Scientists would exchange notes on problems and theories. Many transformative intellectual works of the 18th and 19th centuries were at least in some manner influenced by letter writing. It was how specialists found peers in a geographically dispersed world. 

Having participated in versions of this, particularly during the early blogging era, there’s something uniquely generative about being forced to explain yourself in long form text. And there’s something healing and inspiring when peers respond with care and understanding. 

This practice has fallen away. In its place is the corrosive deluge of social media that trades contemplation for ad-friendly junk food. Or equally capitalist newsletters that turn the writer’s inner life into a never-ending grind to produce sufficient content in the hope of reducing subscriber churn. Even the historically important world of academic journals devolved into an incestuous bureaucracy of sclerotic noise. Current systems exhibit poorly aligned incentives to encourage interesting writing. 

Can we design a modern social system that encourages deep writing? I’m particularly interested in using some of the lessons of social systems design I’ve been exploring in the games to create planned social architecture that drive long lived communities. 

Basic structure of a letter circle

Imagine we build a website that guides people through the following:

  • Someone starts a group in a topic area of interest. 
  • They invite up to 50 people with domain expertise to the group. 
  • Each member must post at least 1 long form letter on the topic each year. This is sent to all members of the group via email. There may also be a web interface.
  • They must also post at least 2 responses to someone else’s letter. 
  • If a member does not fulfill the requirements, they are kicked out automatically at the end of the year.  
  • There is a recruitment phase where any member may recommend new members who then go through the automated invitation process. 

This covers the basic mechanical operation of the social system. We start with group formation and then onboarding new members. Next we establish social reciprocation loops. There’s also a simple measurement of participation. And ultimately a feedback loop for encouraging homeostasis. This takes the form of culling of inactive members and replenishing the group back to the ideal social density. 

What is a letter?

The central social action at the heart of this system is the letter. A letter is a thoughtful piece of writing, one to six-ish pages in length on a shared topic of interest. It is sent to people you respect and hope to correspond with. 

What letter might contain

Letters can take many forms.

  • An observation that starts a conversation
  • A problem that you are trying to solve that may be of interest to others. 
  • A cognitive tool, model or perspective you’ve stumbled across that has been helpful in a specific context you’ve encountered.
  • A description of events in your life this year. Either relevant to the group topic or your personal life. Sharing builds intimacy and trust.
  • A well-considered response to a previous letter.  

The whole point of a letter is that it contains thoughtful writing. Every writer should aim to create something that is meaningful to other members of the circle and prompts useful and interesting responses. 

What a letter is not

  • It is not a full research or white paper. Most people don’t have time to either write or read laboriously formatted texts.  Sticking within the page limit will help writers communicate more clearly and it will ensure exhausted readers don’t bail on page 23. 
  • It is not a short tweet. Complex thoughts need space to build and reveal their finer points. 
  • It is not a blast intended for everyone on the planet. You know the audience! It is your peers in the letter circle. Letters are about collaborative communication, not clout. 

Motivations of letter writing

Western society promotes the propaganda that nothing is worth doing unless you are being paid for it. This is a lie. I think folks will write letters to their circle due to the following intrinsic motivations. 

  • It feels good to stretch your mind and organize your thoughts through writing. This is a delicious form of mastery that many clever folks crave yet have no structured outlet. 
  • It is wonderful to connect with an audience of peers who respect and respond to your thoughts. 
  • We bond with one another when we share our innermost thoughts. And these social bonds can last a lifetime. These relationships become as important long term as eating and breathing. 

If you don’t like to write, read, think or connect, a letter circle probably isn’t the hobby for you. That’s fine! Twitter and Facebook have you covered. But there’s at least single digit percentages of humanity that would be thrilled to engage. 

What is a response?

A response is a shorter discussion of the letter’s finer points. Ideally it is respectful and collaborative in nature. It tries to be on topic. A response successfully closes the social reciprocation loop and builds social capital in the community. By requiring responses as part of the letter circle’s social contract, we sidestep the current issue with blog posts where people just end up shouting into the void. Writers will know someone is actually listening. A good response might contain:

  • An alternative perspective on the letter’s topic. 
  • An example that supports or provides nuance. 
  • A riff that builds off the letter’s topic. 

A good response is additive. You are playing creative tennis, lobbing ideas back and forth to make something grander. 

What a response is not

  • It is not a pithy, short comment. “Great!” “Love it!” “Wrong!” None of these are useful responses since they add nothing to conversation. 
  • It is not off topic. If you want to write something on a different topic, split it off into a new letter. 

New member onboarding

To start off a new group, you need to invite participants.  


There is a web interface that lets you invite someone to the group as long as the active population is under 50 members. 

  • Enter the new member’s email. 
  • Send a templatized invitation. Each group can customize their invitation text as desired. 
  • Press send. The invitee will get an email with the invitation text and standard instructions on what they need to do next. 

Onboarding for a new member

Once someone is invited, they must submit a letter on the group topic within a three month window. This gives them access to the group. If they do not write that first letter, the invitation is withdrawn. 

To help them make this important step, there’s a guidance page included in their invitation with the following:

  • A description of the group’s focus and higher values.  This helps create a shared higher purpose for the group.
  • Advice on formatting, length and topics. 
  • Samples of past letters the group deems to be high quality work. 
  • The rules around participation and removal from the group. This is the upfront social contract; critical to establish early in a crisp, clear fashion.

New users do not lurk. They must post. The goal here is to encourage new members to perform and contribute immediately. Their first letter is their debut. Even if they write nothing else in future years, they’ll have added value to the group with that first letter. 

Who gets to invite members? 

There are several options and which one works likely depends on the culture of the group. Some options are more complex and require additional work to implement. 

  • Anyone can invite: Anyone in the group can invite someone.
  • Group owner can invite: Whoever is the leader of the group can invite. 
  • Group moderators can invite: There’s a small group of people who are allowed to invite. 
  • Voting: Anyone can submit an invitee, but the group as a whole must vote on who gets to actually be invited. There are multiple voting mechanisms such as anyone being allowed to veto, or at least three people must vote affirmative. There’s lots of fruitful exploration here to be done to create systems of mediated shared leadership.

In general, smaller groups need less complicated official management structures. A 20 person group can easily get by with the group owner doing the inviting. A 50 person group may benefit from multiple moderators sharing the duty. If it is a particularly contentious group, voting may be the best option. 

Why the limit of 50 people?

Hyperscaling human networks are another lie technologists tell people with money. 50 seems to be about the limit at which a functional, self-managing group can form meaningful relationships and have useful conversations. Beyond this number, people tend to shut up. They don’t know who is in the group, so they become wary and stop sharing. Or there’s so much chatter people start to tune out the group as pure noise. 

Smaller groups can also work, but they risk not having enough volume of interactions to avoid stall conditions. Maybe no one responds in a timely fashion. Maybe you forget the group exists. 

So think of 50 as a number that is likely to work, but the service may need to tune it to find the actual sweet spot to maximize engagement. 

Requirements for membership

There are two main requirements to stay a member of a group

  • You post a high quality letter once a year. This ensures that the group provides value to its membership. A healthy group will be providing 30 to 50 high quality letters a year. That’s not an overwhelming amount of things to read each week, but still a useful source of information on a specialized topic. It also doesn’t put a huge burden on each member. Most of us can write a couple pages once a year. 
  • You write a high quality response to a letter at least twice a year. This ensures that people who write feel listened to. It creates a reciprocation loop that turns the group into a supportive community. One of the worst things about the modern media landscape is that we are all shouting into the void. A meaningful response from trusted peers closes the loop. 

What is an active member?

If a member fulfills both requirements they are determined to be an active member. This comes into play for reminders and automated pruning of the membership list.

There’s a big design goal behind this concept. It turns out that one of the most important things you can do for a social system is maintain a desired density of active users. You need a certain number of people performing social actions and bumping into one another 

Unfortunately most social media user facing metrics are vanity metrics, not functional metrics that reflect the pragmatic operation of the social engine. It doesn’t matter how many followers you have if none of them are active. It doesn’t matter how many friends on your friendlist you have if none of them have logged on in ages. 

What is high quality?

Quality is determined by the group. This is likely to be an ongoing discussion and there is unlikely to be one correct answer. Two implicit tools for managing quality

  • Define the group’s expectation of quality in the posting guidance page. As the group learns what quality means to them, they can update this text. 
  • Manually kicking people out. Groups may want to cull members who have broken some group norm or simply not performed up to expectations. There’s an admin option to remove someone from the group. 

Automated group management

Most naturally forming groups like mailing lists or group blogs are kept alive by the energy and attention put into the group by a leader. But leadership is rare and unreliable. One solution is to automate as much of the basic nuts and bolts of running a successful group. This ensures that even people who are not amazing leaders can still participate in a well managed and maintained group. 

Automated reminder emails

Several times a year reminder emails go out. 

  • People who haven’t posted a letter are encouraged to post. With the note they will be removed if they do not. 
  • People who haven’t responded to existing letters. 
  • People who have posted get a celebratory list of existing letters. Often people miss an email or two so it is good to showcase what’s available. 

Ideally, the reminders are edited initially by the owner of the group and signed by them. Users are more likely to react when nagged by a human with whom they have a relationship.

Automated culling

Kicking people from a group is a drama prone act. We seek to reduce drama while still maintaining the health of the community by automating this process. 

  • A final reminder email goes out one month before a member is removed from the group encouraging them to fulfill their requirements. 
  • If they still do not submit a letter, a very gentle letter is sent saying that they are being removed in order to make room for a more active member. 
  • Removed members can still be reinvited at a later point. Of course they’ll have to submit a letter to be accepted. 

Manual recruitment

If at the end of the year, there are less than 50 people in the group, an automated reminder is sent out to all members to use the chosen invitee flow. 

  • Unfortunately we can’t automate this step. 
  • We can however establish this in our onboarding materials as a sacred duty. Every new member should be told repeatedly that the group will die if people are not invited. And they are responsible for supplying emails. 
  • If not enough invites are sent out, an escalating series of automated reminders are sent to all members. 

Miscellaneous notes

Optional publishing

The system works fine as a private group. However, some groups may wish to publish either the original letters or the letters and comment more publicly. Some options in escalating cost. 

  • Publish to an existing blog. There’s lots of great blogs out there so no need to reinvent the wheel. This gives folks a lot of flexibility if they want to have a special domain for their group. This comes at the cost of maintaining an interface or plugin with a third party. 
  • The service is also a blog: This service could have a blog-like function that turns letters into web pages. This has the benefit of being self-contained. But now you have to also write blogging software. 


The letter circle system is ultimately a service. Admittedly not a very complicated service since it mostly sends emails to a small group alongside a relatively minimalist web admin UI. Still servers cost money, as does initial programming and ongoing maintenance. There are several options

  • Volunteers: If the service is small enough, a volunteer could fund most of the hosting costs of a global service. I suspect you could serve a lot of groups for even $1000 or so a year. Getting someone to devote programming time is always more problematic. 
  • Crowdfunding: Members of successful groups could donate year fees to keep the group or the service active. 
  • Self-hosted open source: The service could be released open source. 

Note: There’s absolutely no need for this to be a scalable profit-driven VC-backed entity. Business models often poison honest relationships between trusted peers. You could shoehorn in an ad-driven business model. You could slap on a subscription service. But, you know, none of these are required to support the core intrinsically motivated reciprocation loop. 

Expected Dynamics

There’s a life cycle to a letter circle. I don’t fully know what it might be having only experienced analogues, but I have some guesses. 

  • An initial burst of invites. However, this will result in only a handful of letters. Getting anyone to commit to anything these days is difficult. A new circle would need to send out many dozens, maybe even hundreds of invites to get enough participants at first. 
  • Sticky joiners come from high trust connections: High trust, high respect invites between friends are the most likely to get a response. But people only have a limited number of these relationships that they can draw upon to seed a circle. 
  • A slow start: Most circles will start with 2 to 5 active members. If they fail to invite more, activity will eventually fade away and the circle will die. 
  • Community in 2 to 5 years: If a circle can last several years, there’s an opportunity to build up bonds between members. At this point, the circle is far more likely to survive. At this point you may want to start in person meetups to convert those bonds into life long friendships.

One of the implementation tasks is watching how circles behave over time and creating support mechanisms at critical phases. 

  • Maybe there needs to be looser requirements and more reminders to invite people in the early stages. 
  • Maybe extra work needs to happen to encourage responses from members to ensure friendships begin to blossom.


This post could have been a letter. True, it is longer than hoped, but it almost fulfills the goal of being a thoughtful bit of long form writing. Unfortunately I have no circle of social systems designers to share it with. What a pity. 

Take care, 

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