Collectives are an organizational structure for bringing together people to share the legal and financial challenges of going it alone professionally, without embracing the mechanisms of the corporation.

I propose collaboratives: an organizational structure for bringing people together to share the social challenge of going it alone professionally, without embracing the mechanisms of the corporation.

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In a recent blog post, Casey Liss concluded a discussion of using Claude Code with this observation:

While I’m incredibly lucky to be able to work for myself, and I have astonishingly great humans as my podcasting coworkers, I often feel very alone when it comes to my development work. What I miss about having a jobby job  —  more than anything else  —  is working as part of a team to solve a tricky problem.

Claude and I are teammates now. And boy, did I miss this feeling.

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It’s not the same, of course. I’d vastly prefer to have a real, human, teammate. I’d love it if Callsheet did so well that I could employ someone to work with me. It would be better in darn near every way.

But in lieu of that, this is pretty great.

My thoughts about this particular experience report aren’t all that complicated: this is one of the reasons I think the chat interface for LLMs is pernicious and bad and should be done away with — even if we solved all the other problems with them. But that’s a post for another day; this is just context. As Casey and his cohosts discussed the post further on this week’s episode of ATP, John Siracusa commented that LLMs are a poor substitute for people, and they ended up discussing the loneliness of indie developer life.

That is definitely an experience I recognize: I spent a lot of time working independently during the mid-2010s as I attended seminary, and spent much of 2024 in that mode as well. There are a lot of ways that indie work is wonderful. The solitude can become wearing, though.

Both coworking spaces and third spaces like coffee shops partially address the social needs of being indie, but only partially. Neither comes with the commitment of a long-term partnership that a corporate engagement brings, though. Nor does either come with the promise of collaboration. Both of those matter, so I will take them in turn.

First, on long-term partnership: corporate life is not exactly a secure gig these days, but most people spend years in any given role, surrounded by other people in similar roles. There is an expectation of knowing and indeed of working with the same people day in and day out. You get to know each other’s strengths and weaknesses. You learn from each other. You sometimes annoy each other. You come to rely on each other. The (relative) durability of those relationships is what makes for effective teams. It is also a big part of what makes corporate life tolerable. Its absence in a coffee shop acquaintanceship, still less in the rest of indie life, is part of what makes it feel lonely.

Second, on collaboration: I know a few other software developers who also frequent my favorite local coffee shops. None of them are guaranteed to be at one of those shops on any given day, though, and none of them overlap with the kinds of work I do. We could help each other in a general way: Lots of programming is alike in the broad strokes if different in the details. Moreover, rubber duck debugging is universally useful, and sometimes more so when the audience is less familiar with the details. For many of the thorniest kinds of problems, though, you need someone with similar expertise who can help you dig and dig and dig until you get to the root of a problem. Those coffee shop acquaintances might be willing to try to help out occasionally, but the nature of the relationship doesn’t justify more than that.

Finally, although online communities exist for every vocation imaginable, they generally lack the expectation of mutual availability and, albeit to a lesser degree, the relational durability. (I’d be curious to know if there are exceptions!)

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And so, what if we started collaboratives — long-term partnerships between indies, with an aim to tackle not the financial and legal but instead the social and collaboration gaps in indie life? Indies with a shared vocation would commit to be available to each other regularly. Software developers would be ready to do some pair programming or working through a design or architecture problem on a whiteboard. Composers could give each other an ear trying to get unstuck on a particularly challenging transition or orchestration question. Writers could discuss drafts or work through plotting or outlining together. The key is that these kinds of mutually helpful interactions would happen again, and again, and again, because of the commitment to be available to each other consistently and for the long term.

I have a lot of questions about how this might work; after all, the idea is only four hours old. Should this be a legal arrangement parallel to how collectives work — maybe even an adjunct to existing collective setups? How should membership work? Are there dues? What is the expected availability to help out fellow collaborators? How do you deal with the folks who take disproportionate time and energy without giving back? Individual collaboratives could choose different answers to any or all of these, of course, but having some basic guidance for starting out would be helpful.

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I don’t expect to be indie again anytime particularly soon, though I wouldn’t be surprised if I end up in that world again at some point. If I do, maybe I’ll find a way to make something like this exist. In the meantime, nothing stops you from doing it. And maybe some of you already are. If so, tell me about it!