We are doing a "Freelancer Coworking" experiment in the DS|CAFE Discord server for a week. Will it give isolated freelancers a sense of support?


Happy Monday! Today I started a new experiment on the DS|CAFE Discord Server called Freelance, Inc to create a microcosm of a workplace centered around freelancing activities.
This is an experiment in the grand tradition of trying out a bunch of stuff and seeing what happens, adjusting as we go. To keep it focused, only actively freelancing members who have joined are allowed to post, thought anyone can see what's going on.
To help get started, I wrote up some guidelines based on the formative discussion in our main chat room.
The Starting Format
First, I set some basic assumptions about why we're doing this, and cited some ideals for the kind of culture I thought would be encouraging.
- There is no hierarchy of freelancing! Everyone is doing their own thing and we're all awesome for doing that! It doesn't matter if you've been freelancing for a zillion years or are just getting started. We're all here to support and share for mutual success.
- We can pick a role or department (of one) that we're representing professionally; you can pick several of them as freelancers wear multiple hats.
- The vibe is that of a workplace where we are all on friendly terms and wish success for everyone. The ideal is that it is the kind of place where one can share without fear of judgment or being talked-down to.
- We can talk about any issue related to freelancing and related business stuff! If you are looking for a sounding board from fellow freelancers, or workshopping some work, that's totally cool.
- We are starting with this single room, but can expand as needed. If the experiment looks like it was helpful and has some minimum level of engagement, we can keep it going for as long as people want.
Starting Process
Next, I set some suggested activities for minimal participation as well as general rules to help keep the vibe helpful and egalitarian.
- We have a daily check-in and check-out.
- To promote the feeling of accountability to producing work and sharing acknowledgement of progress, we can post what we're working on and report what we finished. In return, participants can provide a thoughtful acknowledgement in the form of cheering progress on.
- We do not give unsolicited feedback on work shared, unless the posting person asks explicitly for it and provides a hint about what kind of feedback they like.
Creating Safety
Lastly, I wanted to ensure that participants knew that it was ok to try stuff out because it's an experiment! There's no judgement! We're just seeing what will happen and hoping it's good!
Do not worry about breaking things or cluttering up the channel. It's an experiment and we will figure things out as they happen!
The creation of this freelance channel is one of the first purposeful attempts to build a tiny part of "The Colony", which I first referenced in my 2023 Groundhog Day Resolutions post: to have the kind of community I wanted, I had to have a place that was capable of supporting its needs. Infrastructure! Culture! Prosperity!
Here's how I originally outlined the elements of The Colony:


In the new Freelance, Inc channel, we'll have a chance to test the bones of this idea in the so-called "Public Square" that is ringed by our various freelance businesses.


November 2025 Building Challenge Posts
URSYS Web App Template code01
Embedded TypeScript Apps in Eleventy code02
A Review of Old Work and Stories coll01
Eleventy Templates for Atom Feeds blog01
Productivity Energy Crash prod01
Workshopping the 'Activity Bingo' Form prod02
Last Run of ETP Notebook Production tool01
Activity Bingo Form Progress prod03
ETP Mini Notebook Printing Press Tour tool02
Identity and Logo Thinking Pass coll02
Unprofessional Business Cards card01
Word Counting Calendar Reboot wcal01
Word Counting Calendar Interim Release wcal01
Calendar Layout Code Progress wcal02
Super Simple PDF Progress wcal02
Articulating Friendship docs01
First skip day due to day trip to Concord, etc. prod04
A PDF-LIB Reference docs02
Programatic Drawing of Word Counting Calendar Blocks wcal02
Minimum Progress Despite Nausea; useful noobly attitudes wcal03
Calendar Day Drawing Progress wcal04
Progress noted in Groundhog Day Resolutions for November 11 ghdr01
A Mythical Magical Adventure Cat Primer docs03
Correct Calendar Layout Progress wcal05
Calendar Labeling and Space Filling wcal06
A Restorative Visit to the North Shore arts01
Alpha Word Counting Calendar! wcal07
Mini ETP Production Update! tool03
Personal Cards Revisited card02
Visiting an Old Friend in Beverly, MA arts02
Experimental Collaboration
The experiment is slated to run for just one week, after which we'll evaluate and see whether we can keep it going for longer. I'm hoping it will provide valuable data to see what works and what doesn't.
If you'd like to check it out, join the Discord and say that you're here to help with our Freelancer, Inc experiment! You can find the server link by visiting the Virtual Studio and Coworking Space page!
BUILD CHALLENGE COMMENTARY
A couple of good progress things today:
- The first load of 250 Mini ETP Notebooks was successfully (?) shipped to Amazon Marketplace, so that's the first revenue generating activity other than freelancing for this year. This is the first tiny step of an expensive bet that I can create a livable income from such activities.
- I've gotten enough feedback on my business card design from last week to feel like I can go ahead and have them produced. Tomorrow I'm dropping off a check for the run of notebooks, and I'll see if I can have the cards produced locally.
I have family visiting for an extended holiday, which I was not quite ready for. This time of year is challenging for balancing family and entrepreneurial endeavor! As this week is Thanksgiving, it's probably going to be tough to maintain good progress. I also have TWO appointments the following week that require two hours of driving back and forth.
We chat about personal projects and challenges on the DS|CAFE Community Discord Server every day. Come visit! Maybe you'll make some friends!
You can reach me at Mastodon or Bluesky. Or subscribe to the blog feed to stay up-to-date.