The New Breaking Smart

Leveling up to a subscription newsletter

Today, I’m turning on paid subscriptions for this newsletter, and pivoting Breaking Smart into a broader-scope platform, as a home for my longer, more ambitious non-fiction projects. Projects that require significantly more time, effort, and research to produce. Subscriptions will be priced at $5/month or $50/year. You can subscribe via the link at the bottom of this email.

Going forward, this newsletter will be a mix of free and paid content. It will continue to feature my usual commentary on technology trends and futures, but it will now also feature serialized output from my bigger, longer-term projects on the same sorts of themes. To start with, I’ll be serializing two such bigger projects here through the next year at least: A series of essays titled The Great Weirding, and a book, The Clockless Clock.

You can find out more about these two projects, both of which have been evolving in research mode for several years, at the spiffy new main Breaking Smart site. Go check it out (warning: there may be a few rough edges!). Then come back here for the rest of the story, details on what to expect, and to subscribe if you choose to.

The Story So Far

Those of you who have been along for the ride for a while know that this site had its genesis in a 2015 essay collection on software eating the world, based on research sponsored by Andreesen-Horowitz in 2014. I published that first collection in 2015 as Season 1, and initially intended to publish a new collection for binge-reading every couple of years. I also started this email newsletter at the time, as a way to keep the momentum going between seasons.

The email newsletter worked much better than I expected. In the last 5 years, I’ve written over 140 issues, and this list has grown to over 7000 subscribers.

The seasonal binge-able essay collection model though, didn’t work out. Partly because I could not find the time to work on ambitious essays in the interstices of consulting work, and partly because the global events shaping what I wanted to write about were simply moving too fast. The weirding, I freely admit, has been inside my OODA loop for the last 5 years.

The gif below, which my artist Grace Witherell made to go along with the introductory essay of Season 2 in 2016, has been updated 4 times in 4 years! My draft of that introduction has gone through just as many iterations.

But now finally, as of Version 4, freshly updated yesterday, the gif seems to capture the gestalt of a meaningfully complete chapter of history, with a clear beginning and end. It will now serve as the anchor graphic for the opening essay of The Great Weirding (which is really Season 2 refactored into a form where I can finally write it), planned for April.

The Great Weirding is the chapter that fits into the liminal passage of history we might call After Harambe to Before Coronavirus. AH to BC. If we know nothing else about the Great Weirding, we at least know where it began and ended, at least as far as evocative symbolism goes. Root causes in the distant past and ultimate consequences in the distant future will continue to be debated for decades of course, perhaps even centuries. But we now have a meaningful chunk of history to think about.

History arriving at some sort of natural closure event to a transformation still doesn’t solve my practical problem of carving out enough time for me to write about it. That is where paid subscriptions for this newsletter come in.

Last year, as my first experiment with subscription models, I started the Art of Gig newsletter for independent consultants. That has now been going for almost a year. I found to my surprise that the subscription model worked well for me, and provided both the motivation to do more demanding writing, and the income support to take time off from consulting work to do so. I didn’t expect the money to get serious, but to my surprise it did. That allowed me to work more seriously on the content than I thought I’d be able to. I’ve now gained the confidence to try the subscription model here. I hope to replicate the success I’ve enjoyed with Art of Gig here with Breaking Smart.

Also in the last year, I was fortunate enough to be on a fellowship at the Berggruen Institute (due to wrap in May), which has allowed me to make significant progress on my other big project aimed at understanding our current condition, a book about the changing nature of time in a software-eaten world. I originally conceived this as a sequel to my first book, Tempo (2011), but it quickly became clear that the scope was much broader and called for a whole new set of mental models. Over the last 7 months, my ideas on that front have finally come together clearly enough that I can begin the writing.

Together, I’m hoping these two larger projects under the Breaking Smart umbrella will put the thinking I do in this newsletter on a firmer, more solid foundation. One that is hopefully more useful, to more more people, in more ways. The two projects are very complementary in a lot of ways. One is a historicist perspective on the great transformation of our times, which has dumped us into a new human condition. The other is a conceptual perspective that theorizes this new human condition, in what I hope is a powerful new way, based on reconstructing our experience of time.

What to Expect

When I moved this mailing list from Mailchimp to Substack in May of last year, I wrote:

Substack also gives me a nice option to painlessly add a track of paid-subscription newsletter issues in the future. I may actually do this. Perhaps a podcast track, or or a track of special issues requiring more research. I don’t know.

I’m open to suggestions.

If I do end up adding a paid track, it won’t be for at least 6 months, since I have too much going on. This track of free issues will continue regardless, of course, as long as I keep writing this newsletter.

This is that move. As promised, the track of free issues will continue. I anticipate about a 50-50 mix of free/subscription content. Most of the one-off takes on current themes will be free. Most of the serialized content from the bigger projects will be subscription-only. But I plan to mix it up a bit and experiment as I go along, to find the right balance between free and paid, one-offs and serialized stuff.

Initially, I will be maintaining a tempo of one issue a week. I’ll alternate paid and free content. I plan to try out a 4-week cycle looking something like this:

1. Free podcast/essay on something current

2. Serialized draft essay or from Great Weirding project

3. Free podcast/essay on something current

4. Serialized draft chapter from Clockless Clock project

Depending on how much subscription income is coming in, I might increase the tempo to 2/week. The more subscription revenue I make from this list, the more time I’ll be able to take off from consulting work to focus on writing. I do intend to continue with consulting though, since a lot of the fodder for my thinking and writing comes from that work.

If I end up with enough of a surplus, I plan to source more research, artwork, and other components for what you see published here. Perhaps I’ll even be able to pay for a research assistant.

Why Now

I originally planned to execute this pivot in May, after wrapping up my ongoing Berggruen fellowship, but the pandemic has accelerated my plans.

Morbid though it might seem, both of the projects I’m unveiling today, The Great Weirding and The Clockless Clock, have very strong salience to what is going on. In fact, the pandemic has provided a grim sort of validation to the models and theoretical assumptions underlying both projects. So I want to start getting my ideas out there into the conversation as soon as possible.

I was expecting some sort of global disruption event to arrive, as a natural narrative bookend of the transformations I have been exploring in my ongoing research. I just didn’t expect it to happen so soon, or in this particularly dramatic (and traumatizing) way.

I don’t believe “normalcy” in any sense we recognize will return (the phrase “new normal” is wishful thinking in my opinion). But a weird new equilibrium is clearly starting to take shape, and it is finally possible to start seeing past the fog of the last few years with some clarity, even if the landscape that is coming into view is a grim, pandemic-devastated one.

Both my larger projects, and the continuing bits-and-pieces thinking I do in this newsletter, are ultimately about this new condition that we’ve now been dumped into, with the door to an old normalcy firmly slammed shut behind us.

We are here now, in what I call the Permaweird, and we have to make sense of it and learn to live in it. The new Breaking Smart will be the vehicle for my ongoing attempt to do so. Next week will feature the first paid-subscribers newsletter issue.

If you’d like to join me on this sense-making journey, consider switching your subscription to paid using the link below. If you’re interested in group or corporate subscription rates, get in touch and we’ll work something out.