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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.

Beyond Optimism and Pessimism


Hello and welcome back to the Breaking Smart podcast. In this episode, I want to pick up where I left off in my December 6 podcast, where we talked about the idea of inventing time. In particular, we talked about how to understand Alan Kay’s line that it’s easier to invent the future than to predict it, and William Gibson’s line that the future is already here, it’s just unevenly distributed. We talked about how to develop your instincts around recognizing when you’re living in a growing timeline versus a dying one.

In this episode, I want to build on that, and talk about how to navigate better in time by going beyond optimism vs. pessimism frames.

Here’s my definition of normalcy: things are normal when it’s easy to guess whether you’re living in a growing or a dying timeline. This doesn’t mean your guess is correct. It’s just means it is easy to guess. The options and their narrative meanings are unambiguous.

How do you know you’re in this condition?

You know by the fact that a particular anticipated event in the future acquires a particular significance, and you use the narrative meaning of that event to judge the good and bad things in the present. Let’s call it the Arrival Event.

For example, in 2012, two such arrival events framing the future for the United States were “software is eating the world” and “immigrants are taking over the country.” Both had implied events when the processes could be considered irreversibly complete. You could navigate around the progress of that process. It would have been your clock in 2012. Countdown timers to T=0.

The Arrival Event usually isn’t a real event. It just has to represent a significant irreversible phase transition hypothesis about history. An undeniable arrival into a new condition. In fact, the event is usually beyond the horizon in the distant future, so you’re always moving towards a horizon that’s moving away from you. But on the other hand, don’t make the mistake of thinking that the Arrival Event is necessarily an imagined arrival into a pure utopia or dystopia. It can be more more real than that. So the Arrival Event you’re orienting around during normal times is somewhere between real and imaginary.

This semi-mythical Arrival Event is the temporal equivalent of a True North. A meaningful but beyond-the-horizon point in time that you can orient around. Just as you often head north, but rarely actually have the magnetic north pole within your spatial horizon, you’re always counting down towards your arrival event in time, but it’s rarely within any actual practical temporal horizon.

Now here’s my claim: the sense of a significant arrival event beyond the horizon is at the root of both optimistic and pessimistic attitudes towards the present. Both are patterns of horizon thinking. Both lead you to interpret current events, which are always a mix of good and bad, in specific ways. Misfortunes seem less burdensome if you sense good times are around the corner, and on the other hand, fortunate events seem less valuable if you feel it is all about to get destroyed anyway soon.

By definition, optimists tend to be cheerful about troubles in the present, and declare that better times are just beyond the horizon: “when this is all over….” X, Y, and Z will happen and things will be better.

Pessimists on the other hand, tend to be gloomy about positive things about the present and declare that the apocalypse is just around the corner: “enjoy it while it lasts….” because X, Y, and Z will happen and then it’ll an apocalyptic disaster.

The thing is, they are both right. Each is living in a particular fork of the unevenly distributed future being invented in the present. The optimist is choosing to live in what they think is the growing, generative part of the unevenly distributed future, while the pessimist is choosing to live in what they think is the dying, degenerating part. One is fighting to accelerate their Arrival Event, the other is fighting to delay theirs.

Importantly, both are just guesses. If in 2012, you thought that the growing future was happening in San Francisco and the dying past was in Pittsburgh, that was a guess about the relative significance of good and bad things going on in both places, in relation to your true north Arrival Event, and you made a choice based on that guess.

The thing about normalcy is that you can in fact make such a choice, because so long as the Arrival Event is in the far future, the estimated growing and dying parts tend to be clearly separated in narrative space, and moving from one to another can be as simple as moving from Pittsburgh to San Francisco. From a city you think is living in the dying past to a city you think is living in the growing future.

Or to put it another way, normalcy is when you can reduce the flow of time to a sequence of two arrows. There’s the past pointing to the significant future event T, and the post-arrival future starting at T, creating a new world. In this scheme, the present Now is not that important because you’re not oriented around it.

You can have the luxury of such a simple mental model because you’re choosing to live in a clearly separated narrative timeline: either an optimistic one or a pessimistic one. The only difference is which of the two arrows represents good times and which one represents bad times.

Now the interesting question is, what happens when you can’t separate the two that easily? What if the future is not just unevenly distributed in the present, but illegibly distributed, so you can’t easily put yourself in the middle of a purely optimistic or pessimistic narrative. This is that schizophrenic sense of being the best of times and the worst of times at once. This is the sense of being inside what I’ve been calling The Great Weirding.

One way to understand the collapse of normalcy is that you have actually arrived at the significant future event T that you were anticipating in normal times.

So T=Now. The countdown timer has counted down to zero.

It is the temporal equivalent of the phenomenon of the compass becoming useless when you are actually standing on top of true magnetic north. It’s right under your feet, so the compass can’t tell you which way to head. It’s a division or multiplication by zero.

So why and how can this happen? Because arrival events are not actually mythical events that are always beyond the horizon. Sometimes they cross over the horizon and get closer and closer, and more and more real, till we’re actually living right through them.

When that happens, the approximate separation of growing and dying futures breaks down. The estimates of whether you were living in good or bad parts of the unevenly distributed future have an encounter with ground reality. And the futures you were betting on have an IPO, so to speak.

And you have to scramble to correct your position.

What’s worse, because you have arrived, you no longer have a future arrival event as a reference measure to gauge the significance of current events, good or bad. You have no way to judge what anything means. You’ve lost your sense of proportion becausw you’ve lost the thing that gave you that sense of proportion. You don’t know what things in the now mean, because you can’t value them in proportion to where you’re going next.

That’s the condition of the Great Weirding. And next time, I’ll talk about how to orient when you’re in an arrival condition with a useless compass.

A Very Slow Takeoff...

Oh, 2020 started already?

Hey folks, sorry for the tardy start to 2020, a year in which I have far too much on my plate, and have had too much random zemblanity coming at me in the Life 🤬😖😬 Happens department.

Which means the projects where I have the murkiest intentions/commitments to myself, like this one, are getting the most derailed. I last sent out a newsletter/podcast on Dec 6, so it’s been like 7 weeks. I’m still not yet ready to get going with this year’s breaking smart (breaking slow?), and this is mostly just a quick Hello-2020 newsletter.

For the next few months, I’m going to slow this thing down to once a month, while I rebalance activities and commitments. For this week, no original content, but here’s some stuff from other channels you guys may like.

I’ll be back with new stuff hopefully in a few weeks, around February end. It’s been a while since I’ve sat down and brainstormed how to evolve this thing, and I need to do that too, since this thing has admittedly mission-creeped and drifted quite a bit over the years, not to mention gone into deep denial about Season 2, which has supposedly been in the works since 2015 and is now over 3 years late. It’s like a military contract project at this point. I know many of you would like to know if/when it’s ever coming out. I would too 🤡🥁.

But we’ll get this show back on the road properly at some point.

Inventing Time


Today I want to talk about time, which is a subject I’m researching quite a lot these days. In particular I want to talk about two of the most-quoted lines in technology conversations that are about time.

The first one is Alan Kay’s, famous line: it is easier to invent the future than to predict it. Alan Kay is a famous computer scientist who was at PARC.

And the second line is from William Gibson, the pioneering cyberpunk science fiction writer, who is famous for the line: the future is already here, it is just unevenly distributed.

What I want to do in this episode is change your understanding of such lines from figurative to literal, where the idea of the future being invented is not in the sense of specific things or events “contained” by the future so to speak, or from the future and “contained” in the present, but time itself as something that is invented.

Let’s start with a few examples.

In the last few years I’ve experienced a few technologies from the unevenly distributed future, as I’m sure many of you working in technology have. And I want to talk about four in particular: riding in a Tesla, trying on an Oculus VR headset, making a cryptocurrency transaction, and trying on a Magic Leap AR headset.

So the interesting thing is, my reaction to these four experiences was different in each case.

On one end of the spectrum we have Magic Leap and crypto. Both of those things, when I tried them, they were interesting, exciting, and stimulating, it was fun to try these things. But neither felt like an inevitable part of the future, at least to me, so subjectively speaking they did not feel like an inevitable part of the future.

In terms of Alan Kay’s line, they were auditioning for the role of being part of the invented future, but they were not decisively part of it yet, at least as far as I’m concerned. And in terms of William Gibson’s line, they may or may not be part of the actual unevenly distributed future. They felt like they might equally well be part of a fork future we may not go down, like I imagine it felt to play a BetaMax tape when it was still a competitor to VHS back in the day. That’s an important idea to recognize, right, that there are technological options we discover, uncover, and develop, but don’t necessarily exercise, and go down the future they create.

The Oculus headset, now that felt a little more substantial, like it was definitely part of the future being invented, but not necessarily an actual piece of the unevenly distributed future that I was experiencing in the present. Something like it seems inevitable, it feels like it rhymes with something from the future, but perhaps what we will actually see in the future is not that exact kind of thing. You can think of it as the future in a beta-test form, or at least that’s what it felt like to me. So I’m emphasizing repeatedly the subjective aspect here because what we’re talking about here is a gut experience of the temporal quality of a technological experience. We’re not talking about rational assessments of future probabilities, we’re talking about how real a sense of time feels.

And finally, riding in a Tesla made the electric vehicle future seem utterly inevitable in a way that kinda killed the present for me. Suddenly I could no longer look at gasoline cars the same way. Driving in my own car felt different, like I was stuck in the past, waiting for the price of the future to come down to the point where I could afford to live in it. So a Tesla creates the future in the sense of both the Alan Kay and William Gibson quotes. It makes the future real in a deep way that is like making time itself real. And you know this because the feel of the present feels different, like you’re heading down a dead-end, a lame-duck future. You’ll have to either abandon it as soon as you can, or end up dying with it.

Stepping back, I think it is important to understand innovation as the process of literally inventing time itself. The mark of success is that the present starts to feel dead, like the past, and the beachhead of the future in the present, let’s call it a Gibsonian temporal colony, feels like a portal for getting back into the present. So it’s almost like there’s been a time shift and you’ve been shifted back into the past and you have to step through a portal to get back to the present. There is a sense of inevitability to your experience of the new technology, and a sense of derealization — things seeming not quite real — in your continued experience of existing incumbent technologies.

You have to get very sensitive to this feeling in your gut if you want to do good work in the world of technology, even though of course it can be very misleading. There is a chance that feeling in your gut, that deep down sense that this is the future being invented, that this is time that is more real than the time I’m living in, that can be misleading. It could be that you’re mistaken. So that’s why I again emphasize this is a subjective feeling. But I think it is a very reliable indicator. When you get that feeling, there is a much stronger chance that you’re going to be right than wrong.

So you have to get very sensitive to this feeling if you want to do good technology, whether as an engineer, an entrepreneur, an investor, or an early adopter making new culture with it. And this is not the same thing as feeling excited or stimulated by the future. It is not the same thing as logically and rationally concluding that a certain scenario is the most likely future, and investing in it. It’s a sort of all-in psychological investment of identity into a sense of time that feels more real than the one you’re in. It’s a sense of switching timelines.

And this feeling can be evoked by very mundane and unexciting things. It doesn’t have to be a big flash-bang feeling.

An example of this: when I first moved to the US, I used a microwave oven for the first time, since they were not yet popular in India. And an Indian friend of mine taught me the trick of microwaving papads, usually called papadums when you get then in restaurants in the US, which are these little dried lentil crackers you typically either deep fry or roast on an open flame. But the microwave cooked it perfectly, and that was the moment when it was suddenly clear to me that that was the future of the Indian kitchen. So that’s a pretty mundane example. It’s not like experiencing space travel or something science-fictiony like that. It’s a very mundane example of switching timelines and feeling that one kind of invented future involving a certain technology is more real than the time you’re experiencing right now.

Once you get sensitized to this feeling of going down one fork of time rather than another, and the idea of more or less real timelines, I think you’re psychologically equipped to be much smarter about how you relate to technology. You’re equipped to be bolder about how you engage with the future. So it’s a skill worth cultivating. In a way, it’s learning a kind of time travel within the present.

And learning time travel is probably figuratively the most important skill you can develop as a technologist. And I know it sounds weird, but this is the reason all of us in technology tend to love science fiction and sort of reach for ways of to think about experiencing time in much more real ways. We are actually training our gut, we’re training our sense of time being real or unreal, learning to make forks and sort of fork-switching decisions at the right time, and getting a sense of are we in the past, are we in the future, are we in the present, how do we get back into the present, how do we actually make part of the future more real and bring it into the present. So these are all sort of temporal mechanics skills that you learn once you start to cultivate this feeling.

So that’s my topic for the day, let me know what you think. We’re just at the 10 minute mark, so looks like I’m back to slightly shorter podcast lengths, and I’ll be back again next week or the week after with my next episode, thanks.

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