Archive of posts with tag 'Writing'

I just watched this excellent interview with Michael Dean on the How I Write podcast.

Michael is an architect and writer, and his writing project is fascinating.

He’s built a framework for thinking about writing that adapts Christopher Alexander’s concept of pattern languages to writing.

If you’re unfamiliar, Alexander created a way of thinking about design and functionality that gave us a modular, nested framework for how to build spaces — from whole cities down to features within rooms. A “pattern” is a loose and modifiable guideline for how a component of a system should work. More defined than a rule-of-thumb, but less rigid than a rule. So patterns can be refined and adjusted to adapt to different settings.

Thinking about writing this way is interesting. Language has similarities to other complex systems: letters, words, sentences, phrases, paragraphs, stories, narratives. It’s made of modular components that nest together in a hierarchy, where ideas (“wholes”) emerge from the interactions between parts, even at different levels in the hierarchy.

Michael’s system gets more abstract than the simple physical form of the words and sentences, into things like voice and tone, cohesion, motifs, stakes, rhythm, and repetition.

Need to spend some more time with these ideas.

This is a phenomenal extended (3 hour!) interview with Dana Gioia on his background, poetry, his writing process, and the habits he’s curated that make him into a prolific and interesting writer.

I’ve been looking for a way to use outdoor time as a spur for creativity. Many of us do our best thinking when our brains and bodies are otherwise occupied — we even call them “shower thoughts” for a reason. Running and walking for me are incredibly productive for the generative part of my brain. I’ve come up with and connected more dots while running than ever when sitting at the keyboard.

Sometimes I’ll walk with phone in hand, usually reading in the Kindle app, but also burning time on social feeds. Depending on what I’m reading I’ll even bring a physical book on walks, as long as I can read one-handed. But then I started going with nothing, just a walk with my eyes, ears, and mind to keep me company. And, as is always the case when the mind has nothing to distract it, the brain is racing with thoughts and ideas and things I need to do and stuff I want to look up when I get back home. But there’s no way to write anything down — fleeting thoughts fleet right out of my head.

So a couple months back I bought a dictaphone. It seemed silly at the time, but I thought “what the hell, I’ll try it”.

Instead of the temptations of my iPhone and the internet in my pocket, I can “take notes”, but they have to be free-form, spoken word. There are voice recorders out there with wifi, AI, transcription. But all of this is irritating ornamentation to me. I wanted the lowest-tech, least-friction method I could find. Hit record, get mp3 file.

And yes, this means I have an audio file with messy, disorganized thoughts. But so what? I can easily speech-to-text it into the computer (more on that in a minute), and regardless, a driving factor here is to get out of my brain’s way. Half the benefit is the “unlocking” effect I get of the no-frills, no-barriers talking out loud. Who cares if I say something that makes no sense? Part of the objective here is to kickstart the mental pistons, get through the messy disorganized thoughts, and find the good stuff.

For me, thinking is modal. Sometimes I need a kick to switch my brain from “consuming” to “producing” mode.

Speaking your thoughts out loud doesn’t come naturally to me. Probably not to many people who aren’t daily podcasters or radio hosts. Having only done this for a little while, it takes practice to speak coherently off-the-cuff into a microphone.

But the improvisational aspect of dictating is one of the most interesting to me. I find myself 20 minutes into a spontaneous stream-of-consciousness, and along the way encountering 5 tangents of other ideas I didn’t even start out riffing on. It’s a fruitful method for getting these latent ideas in my head to crystallize into something tangible. I’ll fork off on some tangent, then the act of thinking, processing, and trying to articulate out lout helps organize the mess into cohesive thoughts.

These audio files aren’t publishable, but maybe one day they might be with practice.

All I’ve been doing after recording is copying the file off the device to my computer, and running a simple command line tool to convert to text locally.

I found this open source tool called hear, which acts as sort of the inverse of the native macOS command say. It uses the OS’s built-in speech recognition APIs to convert mp3 to a simple text file:

hear -d -i voice-note.mp3 > text-note.txt

It’s not as fancy as the online tools like Rev or Otter, but I like it this way. The bulk of the text is a mess of jumbled thoughts with fragments of useful interestingness I can clip out.

Offline, audible thinking is a helpful tool so far. I’ll keep going with it and see how it evolves.

A recent tweet from David Perell prompted me to give this concept a shot.

A short essay on @DavidDeutschOxf's two forms of the Enlightenment: the British vs. Continental model

Continental: We can perfect society
British: We can never perfect, only indefinitely improve pic.twitter.com/svYe22fSzK

— Coleman McCormick (@colemanm) February 14, 2024

I’ve done 3 screenshot essays in the past week, and it’s invigorating. I struggle going from messy, one-liner level notes, or jumbles of bullet points into longer form pieces. The screenshot format is fun because ideas don’t have to be big to contain enough substance to fit a screenshot. In fact, the more compact, the better. 200-250 words.

What I’ve noticed so far is it makes it much easier to remove the friction to expand on tiny seeds from my notebook. For example, right now I have a single bullet in my notes that says “Build for yourself”. If I wanted to write 1,000 words on that idea, it sounds like a big hill. I don’t even know where to start. But 200 words? I could mash that out. Then in the process of the 200ish words, the seed develops into a seedling. There’s some forward progress that kickstarts the creative engine. My last Res Extensa essay began as an expansion on a fleeting clipped quote.

There’s a lower barrier to producing them, easy to consume, easy to share, and importantly, easy to produce consistently.

Substack has entered the arena of the social network wars, taking it to Twitter head-on with a new product called Notes. It’s a short form feed style of posts that runs in a parallel track to your long form newsletter subscriptions (the Inbox), and looks remarkably similar to Twitter. But Substack’s big innovation here for a social network is capitalizing on their subscription-centric model — every other general-use social network on the internet to-date has been based on advertising. From the announcement, how Substack will differentiate:

By contrast, the lifeblood of a subscription network is the money paid to people who are doing worthy work within it. Here, people get rewarded for respecting the trust and attention of their audiences. The ultimate goal on this platform is to convert casual readers into paying subscribers. In this system, the vast majority of the financial rewards go to the creators of the content.

With this launch, Twitter responded by variously blocking Substack links completely, preventing them from being liked/retweeted, or being embedded on Substack domains. Some of these have since been pulled back after some backlash (on Twitter), but still — clearly Twitter sees this as the direct challenge that it looks like. Ben Thompson has a great write-up on the state of the competition between the two platforms.

I’ve been playing around with Notes this morning. At first glance it looks great; I love the feed from users I subscribe to, and it looks like it algorithmically includes users outside of my following network. Following plus adjacent similar users is good with me for discovery. As a writer of a Substack myself, the network effects on the platform have improved over time (with @mentions, recommendations, likes) and Notes stands to widen the funnel even more, hopefully.

Twitter has struggled to make inroads on something Substack has been gloriously successful with so far: long form writing. Notably, Twitter bought Substack rival Revue (which was a great product!) in 2021, and has already shuttered it. For some reason — probably classic disruption theory crippling incentives, among other product execution failings — Twitter can’t innovate away from its core 240-character timeline product.

I’m excited to see what Substack can do with the idea. Even though Notes is still in their domain of text media, the usage incentives for producers & consumers will change dramatically if this new product takes on a life of its own, standing alone from the deliberate, deep newsletter product they’ve been focused on the past 6 years. If they want to enter the social media game, now’s the time to strike, with Twitter seemingly still in a confused state about the future of the platform and where it wants to devote innovation resources going forward. They still don’t seem to know how to break out of the advertising-driven, engagement-bait trap, even with a Big Bet Maker in Elon in the driver’s seat.

Arnold Kling is skeptical on the potential for Notes to fit cleanly into the Substack’s existing incentive structure. But he makes a point here that I think points to the potential of combining long form and short form into a new recipe:

Daniel Kahneman has taught us that our brain has two systems. System One reacts rapidly and emotionally. System Two reasons slowly and rationally. Short-form writing is adjacent to System One. Long-form writing is adjacent to System Two.

We need both systems to have a functioning consciousness. Maybe the same could be true for text-based media.

About a year ago I started experimenting with the idea of a daily journal. From someone within the Roam community, I heard about the concept of Morning Pages, which is a tool for creative writers to build a muscle for generating ideas. Author Julia Cameron defined it in her book The Artist’s Way:

Morning Pages are three pages of longhand, stream of consciousness writing, done first thing in the morning. There is no wrong way to do Morning Pages—they are not high art. They are not even “writing.” They are about anything and everything that crosses your mind– and they are for your eyes only. Morning Pages provoke, clarify, comfort, cajole, prioritize and synchronize the day at hand. Do not over-think Morning Pages: just put three pages of anything on the page… and then do three more pages tomorrow.

Freeform journaling is something I used to do years ago with Day One, but not with a longer free space to ruminate. I mostly used that to document personal events, versus thoughts and ideas. My methodology with Morning Pages has been even more loose than as Cameron defines it. I don’t necessarily get my journaling done in the morning; I just have a goal to do it sometime once per day. The first-thing-in-the-morning writing sessions are definitely the most creative and interesting, but my plan collides with reality and makes it hard to do consistently. The only constraint I set are to write for at least 15 minutes, but my default timer is 25 (more on that in a minute). No topic is off-limits. Often I’ll take some event that happened the previous day and riff on it, or take from something I recently read or a podcast I listened to, or I’ll take a trigger off of something from my Writing Ideas page and expand on existing ideas.

The Artist’s Way’s canonical method is to write longhand, which I agree affords a benefit in mental stimulation that isn’t the same as typing. I’ve experimented a little bit with this and it’s alright — definitely good for the focus and flexibility. Because you don’t need a computer or tablet, you can write anywhere you’ve got paper, and you don’t need access to a particular application. But there are too many advantages to journaling digitally to use the analog method, for me. The key determinant for whether analog or digital is better is: _which one will get you to journal more regularly? Or more deeply?

My tool of choice these days, and for the past 6 months or so, is Logseq, a networked note-taking tool that’s gotten popular in the tools-for-thought space. It’s essentially an open source Roam look-a-like, with a sprinkling of unique aspects.

But the tool itself is irrelevant beyond the fact that I write my journal entries digitally, and that the graph-based model makes for some interesting additional features for the journaling flow.

Logseq has built-in “Journals” — a function that auto-generates a new date-stamped page for each day (like Roam’s Daily Notes). I use the day’s journal for any running activities for the day, things like a scratchpad for meeting notes, reflections on my daily Readwise highlights, general passing thoughts, todos, and my Morning Pages.

I start by creating a block called [[Morning Pages]] and nest the journal entry as blocks underneath. Because that’s a link and a page itself, I can go to the Morning Pages page and see a list of every entry in the linked references. I’ll also add a word count at the top block so I can see my progress. My favorite thing about writing in a zettelkasten-style system like this is the ability to link from within my journaling to other ideas in my notes library.

Then I just write. Sometimes not even in full sentences. And without fail, every time I wall off the time to do this, with no commitments on word counts or topics or boundaries, I can pour out a thousand words easily. My daily average word count is in the 500-1000 words range, but some entries really spark the brain and go close to 1500. Since mid-August I’ve written around 14,000 words in journal entries, and it doesn’t even feel that hard. Mixing in the personal stuff also leaves a nice trail of my thinking about family life and what we were doing each day that I enjoy going back and looking at later. Seeing my old entries in Day One from 7 or 8 years ago is always enjoyable. I’d love to look back in years and have a daily record of my stream of consciousness.

Last week I picked up Scene and Structure on a recommendation I saw from Nat Eliason. I’ve seen him mention experimenting with writing fiction, which this book is about — the process of narrative structure, staging scenes, the balance between scenes and “sequels” to maintain coherence and tension through writing novels, which is the author’s background. I’ve thought about testing the waters with fiction writing, even if I never publish it anywhere. I think the NaNoWriMo happens in November, so maybe I’ll make a plan to give it a shot during that and see what happens.

Anyway, I’m not necessarily interested in the structure of fiction for myself in learning how to write it. For one I just find it interesting how “formulaic” in a way that all narrative fiction is, from novels, to TV, to films. Once you read Scene and Structure, it’s hard not to notice the mechanical elements playing out. You can watch a TV show and almost narrate yourself the structural elements as they happen. The point of Bickham’s guidance is not to distill every writer into following the same exact formula for everything they write, but rather to see the elemental components of storytelling with clarity, allowing you to see the skeletal framework of fiction. Think about cooking. Yes, it’s about recipes and ingredients, just like stories are plot elements and sentences. But becoming a great cook is more than about knowing lots of recipes and ingredients; great cooks know why particular ingredients show up in recipes together, what each is contributing to a dish, and they can assemble subgroups of ingredients in repeatable, predictable ways. Compelling writing — just like compelling cooking — requires knowledge of a structural hierarchy. A mirepoix of celery, carrot, and onion is a known, functioning collection of aromatics that works well in many many dishes. It’s a building block of building blocks. In narrative, if all you have is action-packed scenes connected one after the other, without a sequel in between for characters to digest what happened and mull over decisions, you leave readers confused and overwhelmed. And there are parallels with systems of all sorts, not just cooking.

One of the things I’m most curious to consider with this book is how well the principles could translate to nonfiction writing. Certainly if you read well written narrative nonfiction — Barbara Tuchman, John McPhee, David McCullough — they’re using many of these similar tactics to establish PoV “characters”, create tension in the narrative, and to find meaning in events, versus just “this happened, then this, then this”, which you could fall into easily writing something like history, which is literally a retelling of events.

I’d also started reading Christopher Alexander’s famous work A Pattern Language, something I’ve had on the shelf a long time and have been looking forward to picking up. I’m probably 50 pages into it so far.

What’s interesting are the similarities between these two books. I hadn’t bought either for the same reasons, but the common threads are certainly there. A Pattern Language is Alexander’s guidebook to cities, neighborhoods, architecture, construction. The idea is that composing these places that people live is an exercise in thinking in building blocks. He lays out dozens of reusable components or themes in architecture, from empirical study of what works and why. Well lit rooms, places to sit, greenery in the right places, putting benches next to gardens. Each on its own seems like an obvious thing, since these are components we see constantly around us. Though I’m not far in yet, and haven’t read any Alexander before, I see the purpose isn’t to tell you that well-lit rooms are a good idea, but to see these components as LEGO blocks for design. If you develop a language of patterns for your own work — even something like software — when faced with what to put where in a new design, you can refer back to your book of patterns and find subcomponents that’ll work well in that situation, based on the goal you have for a particular feature.

Thinking about these systems as “languages” is interesting. A language is hierarchical just like the systems these two books present for fiction writing and architecture. You start with letters, build those into words, then phrases, sentences, paragraphs, and so on. You can’t simply insert new elements into a language from the top without considering how your elements nest together and interact with the surrounding existing elements. This is why top-down “designed” languages have never worked. Even attempts to guide, restrict, or control natural languages have largely failed. The French famously have a government body responsible for maintaining what “real” French looks like. Has that worked? Do French people refer back to a government website to determine to some new vernacular or not?

The similarities between systems like these is fascinating to me. In both cases, fiction and architecture, the systems of patterns are developed over time based on empirical evidence of what works. Writers didn’t invent Bickham’s structure from whole cloth centuries back; the concepts he presents have evolved gradually over time. The way writers wrote even 200 years ago bears little resemblance structurally to what a novel looks like today. Writers over time learned what readers wanted, and innovated around the edges while conforming to norms of structure that were mostly predictable.

In the same way, Alexander refers to “the timeless way of building”. Most of the individual building patterns he presents he did not invent. They’re components for comfortable living that humans developed, in some cases, millennia ago. His mission isn’t to tell you new things, but to present a framework for ordering and assembling the things we know work into a cohesive hierarchy.

“Bring yourself back online…“

— Bernard Lowe

When I pumped the brakes on my daily writing routine last year, I had designs on some other interesting projects to spend time on that the daily demand wasn’t giving me space for.

Throughout 2019 and 2020, I’d built a decent muscle for repetition and managing good habits through the accountability of publishing monthly reports on each goal. The first of each month I’d put together my stats on progression. I never shared them widely, but the act of putting it out there on the open web on a regular schedule created a forcing boundary to go through the motions of self-reflection. I was writing a post each day (with a fairly low bar for what constituted a post), running regularly to hit an annual miles target, meditating, and tracking the books I read.

In the fall I started writing Res Extensa, a newsletter project on some deeper themes, which is something I’d wanted to do for a long time on the blog, and occasionally did, but the need for the daily heartbeat of publishing didn’t give me the breathing room to spend much time on longer pieces. Time is precious for most of us, and for me it was all I could do to keep up with the goal commitments I made for myself, without trying to make additional promises about a weekly, biweekly, or hell, even monthly newsletter-writing schedule on top.

For 2021 I decided not to repeat my annual ritual of goal-setting in the same way that I’d done for ‘19 and ‘20. I started to lose steam and wanted to take a breather after I hit the two-year mark. In my November update from last year, I wrote how it was feeling like going through the motions rather than driven by excitement and motivation. To some degree that’s the whole point of accountability forcing functions like this for habit-forming: do the reps even when it’s not fun. But beyond the rep-fatigue of many goals, I’d wanted to try working on some new ideas. While I’m down with being aggressive in pursuit of goals, there’s a thin line between aggressive and overcommitted. Overcommitment results in poor performance on all fronts. Focus, by definition, requires fewer targets.

With reading I’d decided not to set a goal as I had the past 2 years, with a book count target for the year. For obvious reasons it’s sort of imaginary to quantify meaningful reading and learning through a raw count of books. If you measure to hitting 40 books per year, you might shy away from deep, challenging reads in favor of quicker ones just to hit a number. This is the nasty downside of bad measurement — you start performing to the measure rather than in service of an underlying goal. In this case, reading interesting things is the real mission; tracking a count is just a way to keep enough pressure on yourself to spend time on it¹.

Running was a goal that I was doing mostly fine with from a time management perspective. Unlike writing or learning, the time input required scales linearly, so it’s easier to fit in. One’s fatigue level isn’t consistent — some days you’re exhausted and really don’t want to do the miles — but at least 30 minutes of time results in 30 minutes of running. 30 minutes of time writing doesn’t guarantee 30 minutes of actual, readable words! My issues with consistent exercise in 2021 so far have been more due to schedule mayhem than anything else. Buying the house and moving earlier this year, plus readjusting and getting settled resulted in not much time left for putting in the miles. I’ve started getting back to it the past few weeks, but exercise is an area I need hard targets for to push myself consistently.

So back to the reboot.

I’m getting back on the horse of writing regularly here, and planning to set some reasonable targets for other goals for the remainder of the year. My thought that eliminating the hard personal goal targets would make space for other things was logical, but paradoxically made me get less done, reducing motivation overall to work on any personal projects. I thought having more time available would make a biweekly newsletter pretty easy, but it’s done the reverse. There’s literature out there on this topic, and many of us have experienced this firsthand: having a compressed schedule of availability focuses our attention on the things that matter most. When we have too much time, things can happen “whenever”, which turns out quite often to be “never”.

In the middle of 2019 when I was hitting all my goals regularly, I don’t remember feeling overwhelmed at all. Time management was better. I wasn’t thrashing my time away with other meaningless activities telling myself “I’ll get to that article later”.

The shift away from hard goals was a worthy experiment to see how much my habit-forming tactics of the previous 2 years worked. It turns out a habit goes away when you stop doing it. I learned that the hard number staring me in the face expecting to be hit is an excellent motivator for me personally, whether I like it or not. It’s okay though, the point of it all is the delicious sausage at the end, not how the sausage gets made.

Earlier this month I passed the 2-year mark of writing on this site every day. If on that first day, deciding to embark on this streak, you’d told me that in October 2020 I’d still be going, 2018 me would’ve laughed it off. Doing it even for a few months sounded impossible.

What helped make it reality was converting writing into a continuous background activity, an ever-present filter for thoughts, ideas, and readings to pass through. Every time I read an article or have an idea, I filter it through the writing lens — Would this make a good article? Do I have a unique angle on this idea?

James Clear writes about how your environment is a strong contributor to effective habit-forming. One of the techniques he describes resonates with me and fits my behavior patterns nicely: staging your environment by putting enablers “in the flow”:

You can apply a similar strategy by designing an environment where good habits “get in the flow” of your normal behaviors. For example, if you want to practice a musical instrument, you could place it in the middle of your living room. Similarly, you are more likely to go to the gym if it is literally on the way home from work than if the gym is only five minutes away, but in the opposite direction of your commute. Whenever possible, design your habits so they fit in the flow of your current patterns.

My writing filter above is a version of this. It’s a context that keeps me accreting ideas together as fodder for writing topics. This perpetual context is one version of an environment that happens to work well for me. I have reminders in Roam, various “ideas” tags, tools to dictate quick thoughts to a scratchpad. And the goal commitment itself eventually builds up enough gravitational force to do its own pulling.

If you can create patterns of behavior to support the building of a habit, it’s amazing what kind of change you can engender in your behavior.

After 747 consecutive days of publishing, it’s a good time to reflect on what I want to do with the site outside of regular posting.

I’ve finally joined the newsletter club! Today I sent out the first issue of a new project, a bi-weekly email newsletter called Res Extensa.

My intent right now is for the newsletter to be a less-frequent companion to the blog, with some highlights of recent things I’ve been reading, writing, or interested in.

As I wrote in the email, I once had an RSS-to-email setup using Mailchimp, for folks who wanted to subscribe to the blog without RSS. It’s a bit clunky, and since I started the daily blogging routine, an overload for inbox delivery.

The name comes from Descartes’s concept of mind-body dualism, as half of a pair of substances: res cogitans and res extensa — translated roughly to “thinking substance” and “extended substance,” respectively. I guess it’s a fitting name; all of the things that extend from my thinking.

If you’re interested in subscribing, head over to the Substack and check it out!

In his latest issue of The Diff, Byrne Hobart looks the economic models behind the boom in independent publishing and unbundling of analysis and journalism happening on platforms like Substack:

Bundles tend to grow until they reach a highly profitable mature state—at which point any change in the underlying audience, or the availability of competing products, seriously weakens their economics. The bigger a bundle gets, the more likely it is that a subset of users are all paying for basically one piece of the bundle, which could be sold separately at a better price. And as soon as a bundle is partially unbundled, there are two options: stop offering the part of the bundle that now has a competing single-purpose product, at which point the bundle switches from optimally-priced to overpriced, or keep offering it and accept lower margins. Bundles grow gracefully and shrink painfully.

There’s been talk in the tech world about a newsletter bubble, that readers have too many, can’t read them, and won’t be able to afford to pay for them. Some worry that we’re simply moving from the bundled world of old media to a fragmented space with hundreds of indies to have to subscribe to. Not unlike going from a $70/mo subscription to a Comcast cable bundle to a sum of 7 different $10-15/mo streaming services. They’re going over-the-top only to result in me paying the same thing for entertainment as before¹. For written content, we once had to subscribe to the entire Washington Post or Wall Street Journal for writers we enjoy, bringing along “the rest” against our will. Now we can follow our preferred writers directly on their own properties.

In the case of journalism and written analysis, looking at it through only the cost lens is too simplistic. I’m a paid subscriber to 4 or 5 different independent writers’ newsletters, paying a sum greater than I did in total previously for all news subscriptions. But I’m getting a product that wasn’t even on offer in the old world model. Not to mention the freedom and range of motion it affords the writer to explore topics on the edges of their interest. Whatever they’re interested in they can explore, no need to stay in a particular lane to conform to the institutional menu.

I think a natural development we’ll see is new institutions forming around these publications, starting out with an independent writer or two and gradually expanding into larger operations. The Dispatch is at the top of the leaderboard on Substack, and they’re in the early days of building a company around it — destined to expand beyond the few core folks writing there today.

I like and generally support the idea of unbundling, with writers branching out to specialize in niches. This is what the internet has always been great for. Even with the novelty of newsletters as they’re discussed in media, the model is strikingly similar to what we had in the 2000-2006 era of blogs, with independent writers building up their own followings and revenue. What we didn’t have back then were healthy (and stable) income streams — it was mostly ad-driven, which is volatile, irritating to readers, and full of temptation to dabble in other less-than-savory means of making money. I don’t think the financial piece was the biggest problem; the tech was also still new and a high barrier to entry for many professional writers. Tools like Substack give consistency in revenue through subscription, no need to muck with advertisers, and simple publishing tools for dealing with subscriber management, authoring, and email delivery.

The more the space expands, though, the more discoverability will be key. Interesting writers getting a byline at the LA Times get sudden exposure if they can break through to getting a piece published. What does that breakthrough process look like in the indie publishing world? Algorithmic feeds of posts based on interests? Suggestions of complementary publications based on your current subscription list? Would it happen at the post level or publication level? Will someone build an aggregator service to bubble up the best stuff? It would be cool if all a writer needed to do was to write something interesting and have it be “picked up” in the right feed².

I’m curious to see what kinds of bundles could be created from a decentralized network of long-form indie publications. If Byrne Hobart writes his own property on economics and business, as do Ben Thompson and Matt Levine in their own ways, could they form a “co-op”-like offering into which they each cross-post a selection of their work? If I didn’t want to pay $10/mo for each of them, maybe I could pay $15/mo and get a mixture of writings from each writer of their choosing. Medium’s Publication product works in a similar way technically, but I don’t know how it works from a monetization perspective. A sort of reconstitution of the bundle, but packaged in different recipes for different tastes.

Even if it feels like there’s a glut of newsletters out there to pick from and too much to read, I’d categorize it as a fantastic problem to have and improve upon. Diversity and experimentation are overdue since the heyday of blogs waned after Twitter and Facebook took over everyone’s attention. Big institutional media companies have only gotten less varied over the years, and few of them have figured out how to stay in business. It’s great to see so many independent writers and intellectuals able to drive a good living off of their ideas, creating “monopolies of one”:

Bundling reacts to differentiated desires by creating a less differentiated publication that’s fairly valuable to everyone. But as the cost of the reader’s time rises, focus pays off. And the subscription newsletter model makes it easier than it’s ever been to profitably focus on exactly one topic, and build a one-person monopoly.

Jumping off from my Friday post on literature notes, I’ve taken the first step here in what will hopefully become something more meaningful over time.

I just finished up filtering back through all my highlights and notes on Matt Ridley’s How Innovation Works over the weekend. Part of what this process helped me figure out is a standard model for organizing literature notes by section, so if I publish the complete notes, they’ll be browsable by part and chapter of any book I have notes for.

All I’ve got up right now are Summary and Key Takeaways sections. I’m going to make myself put together both of these on any book with published notes, which will require deep thinking to distill the content of the book into a few paragraphs and bullet points. Again, I want to publish my key learnings here, not necessarily a complete synopsis or review. Reviews have a different place on the blog, and I’ll still be doing those separately from this.

I like this idea and think it’s something I‘ll enjoy doing. The forcing function of having to write sensible, consumable notes not just for myself, but for others should lead to better thinking. The effort to build coherent notes should be useful for others and create an archive I can openly reference in future writing. The long-term vision here is to eventually draw connections between books, making references between ideas for deeper insights. And if others learn something along the way from my effort, that’ll be fantastic.

If the work is in the open, it’ll make it better and more polished, though polish isn’t a hard requirement. I’m just hopeful that others may find it useful.

“But what about fiction books?” you ask? Or books that are shallow, or simply not good? That’s easy: no one’s making me go through this process for every book. Over time, if there are books in the library that have no published notes, that should speak their value and worthiness. I tend to have pretty discerning taste for what I’m willing to spend time on, so some books may get “read” enough to determine they don’t need to be on the shelf. I do plan on making notes on fiction, but we’ll see how that works out.

I have some other ideas in store for this later on. This is just a start.

With the last several books I’ve read, I’ve been trying to force myself to work through and document literature notes for my highlights, key ideas, and takeaways from books. Using a process (that perhaps I’ll one day go through in greater detail here) in Roam, I’ll scan through all of my highlights and write up notes on the content, editing it into my own words and phrasing. One of the goals of this process is to increase retention and recall, and as Sonke Ahrens suggests, it’s best not to simply copy and paste highlighted text into a document.

With this flow, what typically happens is that I’ll only write a note for about 75% of what I’d originally highlighted, but also expand on some of them with additional thoughts. So for a book with roughly 200 highlights, I could end up with a Roam page of literature notes of, say, 250 or so blocks. Where relevant and possibly useful down the road, I also try and follow the threads to original sources and insert links to those, but not for everything. Wherever there’s specific data cited or something I find particularly worthy of a future read, I’ll capture it¹.

I’ve been thinking about what I could do next with my Library to make it more useful and interesting. I want to find a way to publish my literature notes alongside or within those book pages. From the Library index page I could then mark which books have notes available and make them searchable and discoverable for anyone. This ties to a long-term goal I have to create a system for evergreen notes that could link between book notes and core ideas. Libraries of books are great, but what about one where you could quickly get access to the ideas within?

This is all experimental at this stage, but anecdote so far says I feel like I have a much deeper grasp on the material for which I’ve gone through this effort. If reading is for the purpose of building knowledge and retaining it, it should be well worth this up-front investment of time to get the payoff from all the reading I do. The next step is to incorporate the tactics of progressive summarization to enrich the literature notes and wire them in with other ideas. Being intentional about rediscovery and serendipitous resurfacing of information has been amazing at augmenting memory for me. Combining all of this with my regular use of Readwise makes reading such a more fulfilling experience.

I saw Patrick O’Shaughnessy share this yesterday, a cool addition to his podcast:

Ok trying something new:

A detailed transcript, including some images, that is also segmented by topic.

Would love feedback on what you like and what you don’t, and any ideas on what else you’d want included. Will iterate in coming weeks

Here’s link:https://t.co/oTci0lyXT9

— Patrick OShaughnessy (@patrick_oshag) July 12, 2020

A ton of added work, but clearly an interesting way to add value.

This sort of thing would be an excellent addendum to most podcast shows. For any episode that has detailed references to other works, I always find well-done show notes useful (thinking about EconTalk as an example). What he’s put together here for Investor Field Guide makes me think about other ways of layering different formats for anyone producing content.

Content has a “native” format, a medium it’s best suited for. If a piece of content is a podcast, or a long-form essay, or a tweet storm, to move it to another medium requires a translation step to embrace the strengths of the converted format. Depending on the subject matter, some things suited to a 3-hour conversational podcast just aren’t the same when converted into a text transcript. What Patrick has done here is a good complement to the audio conversation, a companion document that is of highest utility consumed in tandem rather than standalone. It’s partially a transcript plus sketches, images, diagrams as enrichment.

Ben Thompson went the other direction with Stratechery, creating a podcast version of the Daily Update newsletter. In his case it’s not necessarily intended to be additive, but rather an alternative way to consume the written words.

Another thing that Ben did to diversify Stratechery’s content is to create an archive of “Concepts” — essentially an evergreen, expanding knowledge base of topics he covers, outside the regular stream of analysis posts.

One downside of podcasts, specifically, is how much great stuff is locked up in archives that are hard to resurface or rediscover without effort to dredge up old episodes. If a show has an evergreen nature (isn’t topical or news), it’s worth extra effort to layer in other content formats for different audiences. Text makes the content linkable and discoverable. Images and annotation add depth to the material and create a visual component to share across other channels.

I’d love to see more content producers layering in different intertwined streams. It’s a smart strategy both from a content marketing and attention perspective (getting people’s attention regardless of their preferred medium) but also adds richness and context maximizing the strengths of different media.

In Sönke Ahrens’s book How to Take Smart Notes he describes the “zettelkasten” system (the “slip box”) developed by German sociologist Niklas Luhmann. Luhmann created the system to help himself organize notes and thoughts in a networked model rather than a structured hierarchy of folders. The zettelkasten system has a few elements to it to help model different types of notes, how and when you should write them, and how you associate ideas together.

The fundamental piece is the “permanent note,” one in which you develop your own model of an idea, linking it through associations to other information like quotes, citations, and clippings from other works — but with the base attribute that you formulate it yourself in your own words (not a bunch of quotes pasted together).

Andy Matuschak calls these “evergreen notes,” which I think is a better term to describe how they work. The intent with evergreen notes is that they aren’t ever declared finished, that you continue to flesh out and expand on the ideas therein as you learn more. Maybe you even learn revelatory things that change your deep thinking on the foundation of the idea. Evergreen is a better term, to me, than permanent because it implies a living document. Permanence implies completion.

I’ve been kicking around an idea on how I can convert and publish my evergreen notes from Roam as a public site somehow. Once ideas are substantive enough, I could publish them to the web. Any internal links to other evergreen ideas could link to those pages, and links to ideas not yet published could indicate future ideas I’m working on, but not yet ready for public consumption.

At the moment I’m thinking about how I could build this with minimal friction and augment this site with it. Some way that I can publish alongside the blog, but perhaps interlink content between the temporal stream of the blog format and the non-time-bound evergreen notes. As new ideas or additions are worked out to existing ideas, I want a small breadcrumb to appear in the blog feed showing what was updated and the nature of the change, making visible the evolution of ideas over time.

The roamcult has been on a streak of creating tools to extend and improve Roam Research. Here are a few that I’ve been using lately.

Better Roam Research

This one is a simple Chrome extension that reskins Roam with a minimalist design. It doesn’t change much about the utilitarian interface, just some simple spacing and colors (plus Dark Mode support).

+Roam

A simple Chrome extension for clipping quotes into your Roam database. It takes the snippet and source URL and formats them into a nice block to link into your notes.

Roam Toolkit

A toolbox of useful utilities to make Roam better — FuzzyDate is a quicker way to enter date links, spaced repetition tools for memory, custom CSS, custom shortcuts.

Roam Codes

This isn’t really a tool, but this documentation page shows the extensive set of special codes and objects you can use in Roam markup.

A couple of years back, Jason Fried recorded this video of his writing process for drafting an article:

I like seeing the behind-the-scenes of how others work.

I’m currently reading his book How to Take Smart Notes, which is based on, and talks a lot about sociologist Niklas Luhmann’s Zettelkasten system.

📖 Readwise2Roam

I’m liking so far the process of manually typing notes in Roam from highlights in my books. Something about it feels more efficient and leaves me with more meaningful, succinct notes. This could come in handy, though, if I want to pull all highlights directly from Readwise (which I’m still loving, use it every day).

⛴ How computational power—or its absence—shaped World War naval battles

How the battlecruiser in the early 20th century gave the British a birds-eye view of their fleet before the days of aerial photography, radar, or satellites:

To achieve his vision of a centrally controlled battlecruiser force, Fisher needed a clear picture of the threats. So he set up a top-secret room in the Admiralty building where intelligence reports and shipping news from all over the world were aggregated onto large maps that showed the positions of every friendly and known enemy ship.

This was known as the Admiralty plot. Unlike the displays you might see in a modern military headquarters (which may be updated every few minutes or seconds), these paper maps had a “refresh rate” of hours or even days. But they were nonetheless revolutionary, because for the first time in history a centralized commander could look at a representation of the world naval situation, with every friendly force and known enemy force tracked all around the world in nearly real time. The British leadership could then issue commands accordingly.

📲 Interaction Density

This is one of the best arguments to describe why “pro” users on multitouch devices have so much frustration trying to achieve the same levels of productivity they can on a desktop. Even with quality applications, for certain types of work, an iPad can feel like you’re handcuffed.

♟ Chess

Tom MacWright on chess. Reduce distraction, increase concentration

Once you have concentration, you realize that there’s another layer: rigor. It’s checking the timer, checking for threats, checking for any of a litany of potential mistakes you might be about to make, a smorgasbord of straightforward opportunities you might miss. Simple rules are easy to forget when you’re feeling the rush of an advantage. But they never become less important.

Might start giving chess a try just to see how I do. Haven’t played in years, but I’m curious.

🧪 The COVID Tracking Project

The best resource I’ve run across for aggregated data on COVID cases. Pulled from state-level public health authorities; this project just provides a cleaned-up version of the data. There’s even an API to pull data.

✍🏼 Taxonomy of Note Types

Andy Matuschak’s notes on taking notes. This is from his public notebook, like reading someone thinking out loud (or on a screen at least).

✍🏼 The Enemies of Writing

A great piece from the Atlantic’s George Packer, a transcript of his acceptance speech for the Hitchens Prize.

At a moment when democracy is under siege around the world, these scenes from our literary life sound pretty trivial. But if writers are afraid of the sound of their own voice, then honest, clear, original work is not going to flourish, and without it, the politicians and tech moguls and TV demagogues have less to worry about. It doesn’t matter if you hold impeccable views, or which side of the political divide you’re on: Fear breeds self-censorship, and self-censorship is more insidious than the state-imposed kind, because it’s a surer way of killing the impulse to think, which requires an unfettered mind. A writer can still write while hiding from the thought police. But a writer who carries the thought police around in his head, who always feels compelled to ask: Can I say this? Do I have a right? Is my terminology correct? Will my allies get angry? Will it help my enemies? Could it get me ratioed on Twitter?—that writer’s words will soon become lifeless. A writer who’s afraid to tell people what they don’t want to hear has chosen the wrong trade.

💵 Wealth Is What You Don’t Spend

Morgan Housel:

It might seem obvious that savings is your ability to reject what you could spend. But the majority of financial goals are about earning more – better investment returns and a higher-paying career. There’s nothing wrong with that. Earning more is wonderful, just like exercise. We just shouldn’t lose sight of the fact that earning more will do little for building wealth if every extra dollar is offset by a dollar of new spending.

The world is filled with the financial equivalent of athletes who finish every workout with four Big Macs. Wealth, at every income level, has less to do with your gains and more to do with your ability to leave gains alone without cashing them in.

📨 Superhuman and the Productivity Meta-Layer

An interesting response argument to Kevin Kwok’s post from a while back called the Arc of Collaboration. The meat of the argument is that corralling notifications from the dozens of input streams we all have is challenging, and that a “command line”-style interface like Superhuman’s could function as a filter point to visualize the input stream, but also engage with items in real time. A compelling case with mockups of how it could work (if service providers wanted to plug into this sort of “notification nexus”).

🇮🇷 The Shadow Commander

This 2013 piece from Dexter Filkins gives an excellent background on Qasem Soleimani, an important figure now well known after his killing a couple of weeks ago, but prior to that hardly known by anyone other than experts, even with his massive influence in the region.

🌌 Prosperous Universe

I’m always intrigued by complicated simulation games. I remember a few of these “real-time” MMO games being popular in the early days of online gaming. Glad to see the genre still kicking in an era of low-attention-span gaming largely taking over. From the Prosperous Universe website:

At the heart of our vision lies the concept of a closed economic loop. There have been thousands of browser-based sci-fi strategy games before that emphasize military conflict. By contrast, Prosperous Universe is all about the economy and complex player-driven supply chains in which every material has to be either produced or purchased from other player-run companies.

🔗 Roam Research

Roam is an interesting note-taking tool that’s like a hybrid graph database and wiki. I tinkered with it a little bit. Seems attractive as a way to take meeting notes to try it out.

⚖️ Tradeoffs: The Currency of Decision Making

Farnam Street:

Time is our most fundamental constraint. If you use an hour for one thing, you can’t use it for anything else. Time passes, whatever we do with it. It seems beneficial then to figure out the means of using it with the lowest possible opportunity costs. One of the simplest ways to do this is to establish how you’d like to be using your time, then track how you’re using it for a week. Many people find a significant discrepancy. Once we see the gulf between the tradeoffs we’re making and the ones we’d rather be making, it’s easier to work on changing that.

The article reminds me of Sowell on economics. Take this and apply to any other life domain:

Economics is the study of the use of scarce resources which have alternative uses.

💡 The Power of the Marginal

A timeless one from Paul Graham, 2006. On the advantages of outsiders:

Even in a field with honest tests, there are still advantages to being an outsider. The most obvious is that outsiders have nothing to lose. They can do risky things, and if they fail, so what? Few will even notice.

The eminent, on the other hand, are weighed down by their eminence. Eminence is like a suit: it impresses the wrong people, and it constrains the wearer.

Outsiders should realize the advantage they have here. Being able to take risks is hugely valuable. Everyone values safety too much, both the obscure and the eminent. No one wants to look like a fool. But it’s very useful to be able to. If most of your ideas aren’t stupid, you’re probably being too conservative. You’re not bracketing the problem.

📝 PR FAQs for Products

This is an extension of the Amazon mantra of forcing your team to “write the press release” for a product or feature before starting on it. The goal is to concretely visualize the end state as clearly as you can, and get on the same page strategically to outline the why of what you’re building. The PR FAQ is another assistive technique for setting and articulating the goal.

📝 Blot.im

Blot is a super-minimal open source blogging system based on plain text files in a folder. It supports markdown, Word docs, images, and HTML — just drag the files into the folder and it generates web pages. I love simple tools like this.

🖋 Handcrafted Visualization: Precision

An interesting post from Robert Simmon from Planet. These examples of visualizations and graphics of physical phenomena (maps, cloud diagrams, drawings of insects, planetary motion charts) were all hand-drawn, in an era where specialized photography and sensing weren’t always options.

A common thread between each of these visualizations is the sheer amount of work that went into each of them. The painstaking effort of transforming a dataset into a graphic by hand grants a perspective on the data that may be hindered by a computer intermediary. It’s not a guarantee of accurate interpretation (see Chapplesmith’s flawed conclusions), but it forces an intimate examination of the evidence. Something that’s worth remembering in this age of machine learning and button-press visualization.

I especially love that Apollo mission “lunar trajectory” map.

🔥 The Satellites Hunting for Megafires

Descartes Labs built a wildfire detection algorithm and tool that leans on NASA’s GOES weather satellite thermal spectrum data, in order to detect wildfires by temperature:

While the pair of GOES satellites provides us with a dependable source of imagery, we still needed to figure out how to identify and detect fires within the images themselves. We started simple: wildfires are hot. They are also hotter than anything around them, and hotter than at any point in the recent past. Crucially, we also know that wildfires start small and are pretty rare for a given location, so our strategy is to model what the earth looks like in the absence of a wildfire, and compare it to the situation that the pair GOES satellites presents to us. Put another way our wildfire detector is essentially looking for thermal anomalies.

Inspired by Fred Wilson’s AVC blog, I started posting something every day here last year on October 4th. The 1 year mark passed by and I didn’t even notice. It’s become such a part of my mental routine to keep up with that it’s become pretty painless.

Most of my posts are topics I find interesting or links I run across. I find myself zeroing in on themes that tend to appear in my reading patterns. Through the process I’ve also come up with a few recurring “series” type posts to do regularly:

• Weekend Reading — a link list of 3 recent interesting things, posted on Saturdays
• Places — a series where I highlight interesting geographies
• Best Songs — infrequently logging my personal favorites
• Book Reviews — also infrequent, but enjoyable to write when I find the time
• Goal Progress — on the 1st of each month, a review of progress against personal goals for the prior month

One healthy side effect of the blogging habit has been a reduction in social media usage. I still flip through Twitter occasionally, but the majority of my reading has converted to books, RSS feeds, and a handful of newsletters. Through this commitment to writing every day, I’ve had to pare down the amount of time I burn on “wasteful” activities — TV/movies, gaming, etc. Knowing that I have a commitment to keep up with a regular blogging pattern forces me to stay on task with relevant writing and reading.

One thing I would like to explore soon is how I might be able to schedule posts to go out. Since I write and publish this site with Jekyll and Netlify, it’s all managed in a git repository, without a good way to schedule future posts. So I’ve forgotten to push my changes a number of times, discovering a day late that I never published something. I’m toying with the idea of moving to something like Ghost for a more full-featured writing environment. I’ll mess around with that over the next couple of months and see if there’s something there.

Even though I hit the 1-year streak, I have no plans to stop the every day publishing. Let’s keep this train moving.

I’ve been looking for a smooth way to dictate notes and thoughts while hands-free from my phone, particularly while running or driving.

When I run I typically wear one AirPod and have my phone inaccessible in a waistband pouch on my back. Since I’m usually listening to audiobooks while running, I don’t have an easy way to log thoughts or perform the audio equivalent of highlighting things.

I never use Siri at all but for a couple of easy, reliable Shortcuts for dictation. I thought this was a perfect candidate to explore the “Hey Siri” activation support with custom commands from the Shortcuts app (formerly Workflow).

This shortcut from MacStories provides a simple base for appending to a note in the Notes app. This is good, but for my use case I need to be able to do this completely hands-off. Using Shortcuts to capture and send workflow data around typically requires access to the app, forcing the device to be unlocked for it to work. This still could be convenient enough for, say, dictations in the car where the phone is in its mount or nearby, but in my waist pouch it’s totally inaccessible. I don’t want to have to mess with anything at all while I’m in motion running, so I needed something else.

So I logged into Zapier to see what I could do with its webhook trigger. If you send data to Zapier, they make it easy to connect to hundreds of different web services using custom multi-step workflows. Mine was going to be simple: dictate note → append text to a Google Doc.

I created a document called “Scratchpad” in my G Suite account to house any speech dictations. All I want is a temporary placeholder where I can record thoughts to get back to later. Each new dictated note appends a new line with the content. I use a workflow like this to add tasks in Todoist, but I needed something looser and more flexible.

Create the Zap

On the Zapier side, I created a zap with a webhook trigger first. This gives you a URL to copy and bring over into the Shortcuts app.

Create the Shortcut

Create a new Shortcut with these three steps:

• Dictate text — to capture the speech-to-text data
• URL — to set the base URL for the Zapier webhook (copied from your zap)
• Get Contents of URL — this is what assembles the data into a POST request to the webhook endpoint

The only things you need to do here are paste in the zap URL, set it to the POST method, and edit the “Request Body” property. I added a note property and inserted the value of Dictated Text which will pass in that transcription from your dictation.

Setup the Zap

Once that’s done, creating the zap on the Zapier side is only two steps: a webhook trigger:

And an “Append to Document” action event with Google Docs:

I’ve been using this for a couple of days for ad-hoc comments while listening to books. It’s been a convenient way so far to quickly jot things down like I do when I’m reading paperbacks or Kindle. The only downside is that Siri mis-hears things a lot compared to the Google Assistant, which we use a good bit around the house. The dictation is usually passable, since it’s informal and usually close enough that when I review the notes, I recall what I was trying to say and can correct it. If I ever end up with a backlog of notes in there without being reviewed, the error rate on dictation will probably leave me stumped.

📝 nvULTRA

This is a new notes app from Brett Terpstra (creator of nvALT) and Fletcher Penney (creator of MultiMarkdown). I used nvALT for years for note taking on my Mac. This new version looks like a slick reboot of that with some more power features. In private beta right now, but hopefully dropping soon.

⚗️ We Need a New Science of Progress

Progress itself is understudied. By “progress,” we mean the combination of economic, technological, scientific, cultural, and organizational advancement that has transformed our lives and raised standards of living over the past couple of centuries. For a number of reasons, there is no broad-based intellectual movement focused on understanding the dynamics of progress, or targeting the deeper goal of speeding it up. We believe that it deserves a dedicated field of study. We suggest inaugurating the discipline of “Progress Studies.”

Patrick Collison and Tyler Cowen co-authored this piece for The Atlantic making the case for a new science to study how we create progress.

Looking backwards, it’s striking how unevenly distributed progress has been in the past. In antiquity, the ancient Greeks were discoverers of everything from the arch bridge to the spherical earth. By 1100, the successful pursuit of new knowledge was probably most concentrated in parts of China and the Middle East. Along the cultural dimension, the artists of Renaissance Florence enriched the heritage of all humankind, and in the process created the masterworks that are still the lifeblood of the local economy. The late 18th and early 19th century saw a burst of progress in Northern England, with the beginning of the Industrial Revolution. In each case, the discoveries that came to elevate standards of living for everyone arose in comparatively tiny geographic pockets of innovative effort. Present-day instances include places like Silicon Valley in software and Switzerland’s Basel region in life sciences.

🚙 George Hotz on the Artificial Intelligence Podcast

George Hotz is the founder of Comma.ai, a machine learning based vehicle automation company. He is an outspoken personality in the field of AI and technology in general. He first gained recognition for being the first person to carrier-unlock an iPhone, and since then has done quite a few interesting things at the intersection of hardware and software.

I’m now a couple of weeks into writing a blog post every day. I started doing it sort of on a whim because I’ve wanted to write more often, and a forcing function of “something” every day at least drives me to do the behavior.

Writing out ideas helps me clarify and expand my thinking. For a number of years I’ve tried to keep a personal journal using an app, to varying degrees of success. I’ll go through periods of doing well, then fall off the wagon. My entries there have always had a more personal edge, like documenting things the kids are doing and family activities we do. I also keep a health journal there separately for medical- and exercise-related things. This venue I intend to be a place to “think out loud” and share things I’m working on in an open format.

I set myself a personal goal to see if I could post once per day for a month to start out. No other restrictions on what it could be, anything is fair game. I’m experimenting with some repeating varieties of content that might stick longer-term. Once a week or so I’d like to write something longer, more detailed, and related to thoughts or ideas. Occasionally I’ll mix in technical things, notes on books, and some links to things I’m finding interesting.

The process is proving fairly easy so far. I can spend 30 minutes writing something each evening before bed, and work on longer-form things little by little over time. If I can get through the first month successfully, then I’ll move the goalpost out to 3 months and see what happens. My overall aim is to convert writing from a project to a habit — something I just do as a general pattern. Success will be if I make it to each goal marker while still feeling motivated. As comfort level builds, I suspect it’ll not only get easier, but I’ll look forward to it every day.

I posted a couple weeks ago about moving much of my computing activity to the iPad full time. Part of what I had to crack to make that possible was a writing workflow that supported using the tools I prefer, and a method for publishing and previewing with Jekyll.

I’ve been using Jekyll and GitHub Pages for this site for 5+ years. Other CMS systems are interesting and getting better, but there’s something about the total control and simplicity of static sites that keeps me here. This workflow is great with a full Mac setup, but on iPad or mobile, there isn’t a straightforward way to write and publish new content. Most writers wouldn’t want to bother with this and would move to a CMS to clear the hurdles. Given that Jekyll today still requires a working knowledge of git and a command line interface, I recognize that this is highly personal to me, so I wouldn’t really recommend this setup to people focused on writing. But I sort of get a kick out of getting this stuff working and use it as a learning experience.

The main sticking point I needed to solve was previewing content. Jekyll has a built-in web server you can run locally (what happens when you run jekyll serve) on the terminal that generates and serves the site at localhost where you can preview before you publish. On the Mac this is simple: checkout repository, run command to generate site, browse to URL in browser. The first two hurdles aren’t trivial on the iPad. There’s no native unix-like shell on iOS, only terminal apps. This means you need to have a server to connect to to do anything.

My solution starts with running a micro EC2 instance on AWS. For about $10/month I have a full Ubuntu server running, on which I can install whatever I want¹. Getting the site checked out and running locally on the server is fairly straightforward if you’ve got a working knowledge of Linux and comfort on the shell². Next I had to figure out what software on the iPad I could use to combine the writing, versioning, and pushing up to the server for preview or testing purposes. Digging around on this topic I discovered a solution that’s working well so far: a combination of Working Copy and Textastic. The first is a full-featured git client you can use to clone repositories and manage versioning. The second is a rich code editor for iOS that is very impressive in its depth. Inside of Textastic you can add a Working Copy repo as a working directory, meaning your edits happen directly in the repo. With my iPad Pro, I put the Working Copy app in the right side multitask panel so I can manage branching, commits, and pushes while I’ve also got the editor open. In order to access the server and run the site in dev mode, Textastic also has a built-in SSH terminal.

Getting through this initial setup was a bit cumbersome — getting the SSH keys sorted out between my main machine, GitHub permissions, and iOS was a bit of a runaround — but I’ve got it all working smoothly now. One other aspect is that I still do most draft writing and idea-keeping in Ulysses, which is my app of choice for any writing on iOS or macOS. So there’s a step to get the content moved over when ready to a real post in git. I’m good with this, though. I treat Ulysses sheets like idea scratchpads; so I’ll have dozens of partially-written post ideas collected there and little by little turn some into completed articles. Managing this collection of randomness makes for kind of a mess in a git repository, so it’s nice to have it organized elsewhere.

Overall this workflow allows me to stick with the tech stack I’ve gotten used to while affording the flexibility to write on the iPad or my phone. From a writing perspective I find the constraints a helpful aid in focusing on the writing and not getting distracted to mess with other things. I have a couple of other helper tricks I’ll write about later that make working with Jekyll easier. As I work with this flow some more, I’ll make sure to note any other tricks once the comfort of habit sets in.

For the last 7 days I’ve only been using the iPad. I’ve had a 12.9” iPad Pro for about a year, but have only used it in “work mode” occasionally so I don’t have to lug the laptop home all the time. Most of what I do these days doesn’t require full macOS capability, so I’m experimenting in developing the workflow to go tablet-only.

Slack, G Suite apps, mail, calendar, Zoom, Asana, and 1Password covers about 85% of the needs. There are a few things like testing Fulcrum, Salesforce, any code editing, that can still be challenging, but they partially work depending on what I’m trying to do.

I’m really enjoying it now that I’ve gotten a comfort level with navigating around and multitasking features. I find that the “one app at a time” nature of iOS helps me stay on track and focus on deeper tasks — things like writing documents, planning, and of course being able to sketch and diagram using the Pencil, which I do a ton of. I’ve liked Notability so far of the drawing apps I’ve tested for what I need.

One of the biggest things I had to figure out a solution for was being able to write and publish to this website efficiently. Since I use Jekyll and GitHub Pages under the hood, I hadn’t found a simple solution to manage the git repository and preview posts. I’ll go deeper on that workflow in a future post, because it’s a pretty comfortable setup (for me) that others might find useful.

Overall I’m liking working on iPad more and more. It gets easier as I accrue knowledge of tips, tricks, and other workflows.

I write a ton on the computer, whether it’s for our product blog, internal documents, product help guides, this blog (rarely), or many other things, I tend to stick to the same set of tools for different pieces of my writing workflow.

Everything I write, even things like meeting notes only for myself, I write in Markdown. It’s essentially muscle memory at this point. I write for Jekyll-based websites quite a bit, I write issues and wiki pages on GitHub, I keep my personal journal in Day One, and several other places. All of them accept Markdown as input, so I’ve just formed a habit over the years where I write everything that way. So when I paste an unordered list from a note I made somewhere into a web document, it’s already formatted. If the destination for a block of content I wrote doesn’t work with Markdown, most tools have a “copy plain text” option that I’ll use if I want the raw words to format inside of another application (*cough* Microsoft Word *cough*).

Anyway, onto the geeky stuff…

Tools, we all love tools

I try tons of new tools all the time, and I’ve converted through different tools over the years. About 90% of writing is thinking, so being able to flexibly organize thoughts without fighting with tools is paramount to productive writing. Remember that the tools don’t make you write. I try to prevent myself from getting distracted with whatever the new “app of the week” is for text editing, and while having the proper tools is important, if your process ain’t broke, don’t fix it. Just like with todo lists, code editors, and online courses, another tool in the belt doesn’t make you a better producer… producing makes you a better producer¹. If you’re like me, it’s worth posting that above your desk to keep from fiddling with tools and systems and get to work. If you’re doing anything other than typing the words on the page, the tool isn’t going to help you make more letters appear! (I write that as a reminder to myself as much as anyone else.)

Now, with that said, here’s the short list of apps I use for writing, and for what purpose I use each depending on context:

• nvALT: This is the everyday workhorse. Since I write everything in plain text files, this editor from Brett Terpstra is my go-to for fast access to making new files. It’s typically the initial scratch pad while I’m on my Mac. If I jump on a phone call, I pop open nvALT and create a new text file to log notes. With quick keyboard shortcuts, every time I make a file it just appears in my txt directory in Dropbox, which other apps (including mobile ones) can have access to. It’s an unfancy writing tool for longform stuff, but the key is that there’s minimal friction between thought or idea and it being instantly captured in a reliable place.
• Byword: Used for longer-form editing, basically once something reaches the stage of an official piece of content like an article or guide, more than lists or scratch notes. It’s got a great interface for writing in Markdown, and a built-in preview mode for seeing the content rendered as HTML. Stuff that will end up on the web as articles usually happens here.
• Atom: I use Atom for editing things that involve code, or are typically intertwined with code like HTML or CSS. When I’m writing documentation for Fulcrum or contributing to other projects on GitHub, I use Atom.
• Paper, the IRL kind: If I don’t have access to my computer, I don’t feel like typing, or I want to make sketches, I keep field notes around for pen and paper notes.

iOS apps, where writing is typically harder

Longform content doesn’t usually happen much on iOS for me, unless the motivation strikes me to get my thoughts on paper and I’m not at my computer. Mostly from iOS I’m keeping notes or jotting things down.

• Drafts: What nvALT does on my desktop, Drafts does on my phone. Since most of the time from mobile I’m starting with a new file versus editing something in progress, Drafts is super fast for jumping right into a text edit mode to type out some quick notes. Where Drafts really comes into its own, though, are in its Actions capabilities. The idea is that anything starting as a piece of text can be fed into an Action within Drafts to pipe it into any of dozens of other places. Getting to know what’s possible in Drafts is a separate post in and of itself, but needless to say, it’s where I do probably 90% of my text typing on iOS.
• Editorial: I’ve just discovered this app recently after reading Federico Viticci’s stunningly in-depth review, and so far it’s a promising addition to the writing process from iOS. I’ve never been a heavy iPad user, but I’ve been debating jumping back into the iPad world again, particularly for working on something at home on the weekend, traveling, or otherwise mobile without my laptop. This app is ridiculously complex and powerful, and I’ve only started to scratch the surface.

Many people like Evernote and other cloud-based services for dealing with notes, but I like the idea of the archive of text I’ve produced since about 2009 all lives in plain files in a folder — completely portable, easy to back up, and generally friendly to copy or import into other places for publishing. I don’t need separate notebooks or embedded attachments or tagging on my files to get in the way, I just want an editor and the canvas for text. All of the tools I mentioned above have excellent full text searching capabilities, and after 6 years of managing all of my notes this way, search has never failed me for finding what I need.

One thing that my personal workflow doesn’t support directly (or at least I haven’t found a way) is on-the-fly collaborative editing. Most of the content I write is for myself, or at least doesn’t need to have other editors for most of its existence until it’s ready, but maybe there are tools out there I’ve not yet discovered. Currently for anything that needs to be collaborative from the get go I would use Google Docs, since it’s unmatched when it comes to real-time simultaneous multiuser editing. Other than that, anything that happens for publishing via GitHub already can be collaborated on asynchronously using pull requests and commit references, which our team uses constantly.

If readers have any suggestions of other methods for augmenting things, particularly collaborative editing a la Google Docs, ping me on Twitter, I’d love to find more options to make my flow even better.