Yes When I Meant No
Observando | A Change Of Heart (with input from Paris Marx and Max Read)
My successes have always been for different reasons, but my failures have always been for the same reason: I said yes when I meant no.
A Change Of Heart
The ghost of workfutures.io yet to come?
I woke up at 2 am two days ago, unsettled. I had a troubled dream, circling an interconnecting network of work activities I’ve been actively working on and toward, as well as personal objectives and intentions.
I was troubled because the many threads weren’t knitting together, like a large dinner party with too many conversations — or arguments — at one table.
I sat up in bed and thought, ‘Too much is going on in my life and work, and what I am planning will completely disrupt how I want to spend my time’.
I mulled over my many projects and ambitions, particularly plans for workfutures.io. All at once, the various puzzle pieces slipped together, leaving me with the final result: the path I was taking was the wrong one.
TL;DR: jump to the final ‘The Bottom Line’ section if you don’t want the recap of my new reasoning, but basically, I now plan the following:
staying on Substack and abandoning plans to move to Ghost,
shifting the form and flow of the workfutures.io newsletter slightly,
dropping plans for a Mighty Networks community site, at least for 2025,
starting ‘unoffice hours’ — regular video meetings for subscribers and one-on-ones with sponsors (paid subscribers), and
recommitting to developing a series of ‘booklets’ (booklets are to books what novellas are to novels) on topics like decision-making, making remote work work, and the emergent organization (free for sponsors).
I am eager for these changes, driven by the desire to spend my time on what I now feel to be most important to me, not just some hypothetical financial growth plan.
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First, thanks.
I want to thank all the followers, subscribers, and sponsors of my work at workfutures.io over the years. I am betting that the changes in my plans won’t disrupt all those reading and interacting with my work. At least, I hope so.
The most significant shift may be for sponsors since I will offer them new opportunities to interact with me — and each other — in ways I haven’t undertaken before.
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What I had been planning before my troubled night.
I’ve been contemplating significant changes in the infrastructure for the workfutures.io project.
I’ve been open about building more community support for workfutures.io, and in recent weeks, I had come down on building a Mighty Networks community and inviting subscribers and sponsors to participate. I knew this would take effort, but I hoped it would provide value for members. But that morning at 2 AM, I realized it would take a tremendous effort, much more than I had been willing to admit.
A lot can be developed with a Mighty Networks community, but I realized that morning that I had thought about it all wrong; Mighty Networks is intended for situations where the network is the product — membership in the community is what people pay for, come for, and come back for. It’s not intended to be an adjunct to a newsletter. Not really.
I realized (that early morning) that I was headed for weeks of work every month for something I had not tested with sponsors, subscribers, and followers and when all community-ish things I’ve tried in the past haven’t taken off.
Secondly, I contemplated transitioning from Substack to Ghost, an alternative newsletter/hosting platform. I wanted to cut the fees associated with posting the newsletter and was concerned about the Substack organization's politics: they seem willing to host some far-right newsletters. However, after reading about the experience of Paris Marx — who made that exact transition and returned to Substack — I’ve reconsidered. Here’s his take:
I launched Disconnect in February 2023 and through its first year I was regularly meeting or exceeding the targets I’d set for subscribers and paid supporters. I was excited about the trajectory the newsletter was on and making plans for its future. But soon after moving to Ghost last year, the newsletter’s growth effectively flatlined, stifling those plans and eventually sapping my motivation too. As 2025 approached, I started to reflect on what it would take to reinvigorate Disconnect — and that meant making some tough decisions.
When I moved the newsletter off Substack, a number of writers I respected like Max Read and Parker Molloy refused to do the same because they believed that leaving the platform would make their newsletters unviable. Max Read, for example, explained that while Substack was good at sending emails, the real reason he was staying despite everything was because of the network effects.
In addition to “writing emails” and “sending emails,” the other main thing you need to do as a subscription-newsletter proprietor is find new readers. Even if you don’t want the business to grow in absolute terms, and would be happy to maintain a constant level of revenue, subscription businesses need to bring in new subscribers to make up for “churn,” or the regular portion of subscribers who cancel.
What makes Substack valuable to publishers is that it leverages its size and newsletter network to bring me new subscribers without me having to do anything.
Last year, amid the stress of having to respond to the controversy and plan a platform migration over the holidays, I thought people like Max must be wrong; that they just weren’t willing to make a difficult choice. But my experience of the past ten months has taught me the opposite. Sadly, he was right: Not being on Substack made having a viable newsletter — at least of the type I write — far more difficult.
Marx and Read confirmed some of my fears about Ghost. I knew the transition would involve much time and effort, even if Ghost provided their concierge service to help me. And, of course, I’d be leaving behind Substack followers, whose email addresses I can’t extract from Substack and who make up the most obvious pool of possible future subscribers.
Yes, it entails making a compromise since I don’t approve of all Substack is up to, but it turns out Ghost also has some issues. As Marx points out,
On the “creator” front (or whatever you want to call it), people who moved to Ghost continued to use Shopify to run their online stores, a company that’s long defended its choice to provide its services for stores selling Nazi memorabilia and far-right merchandise. Ghost itself promotes the fact that Quillette, a right-wing online magazine most closely associated with the “intellectual dark web,” is one of the highest grossing websites using its software, while competitor beehiiv courts the scam-laden crypto and web3 industry. All of these platforms have their flaws.
Yes, all of these platforms have their flaws. So, for now, I am staying put with Substack and not diving into Mighty Networks.
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The Bottom Line
So, I have dropped some planned changes and am undertaking something more modest, especially concerning the time I would have to commit to those now-abandoned plans.
Shifting form and flow — I intend to make the newsletter issues smaller and more frequent. Expect a new format with three sections: a quote from which I derive the issue’s title; a core section with one (or at most two) long-form commentaries; and an optional section with two or three short, curated selections, which will take the place of the previous Factoids and Elsewhere sections. I plan to write at least three issues a week, one exclusively for sponsors.
‘Unoffice Hours’ — I will launch (by early February) a regular hour-long meeting for sponsors. I haven’t pitched the platform yet (looking at Zoom and Google). I will also be opening up scheduled one-on-ones with sponsors (paid subscribers), with a first-come-first-served basis (about which more later).
A series of ‘booklets’ — As I said, booklets are to books what novellas are to novels. I’ll be developing booklets on topics like decision-making, making remote work work, and the emergent organization. These will be free for sponsors and for-fee for others. I haven’t worked out the platform for distribution yet.
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Again, thank you all.
When I woke up at 2 AM the other night, one of the dream-like aspects of the experience was this: I envisioned the various projects in my portfolio as family members arguing around a dinner table, each demanding attention and talking over the others.
Perhaps that’s an echo of the opening line of Anna Karenina by Tolstoy:
All happy families are alike; each unhappy family is unhappy in its own way.
My family of projects and activities was unhappy in its own way, but now I hope to find a new balance and make the family happy again.
Thanks for your support and forbearance.