Accountability, authenticity, media, confidence, time-boxing; practices for writing and thinking with Avvai and Kyle

Accountability as a spur of the winter work

After reading Kyle’s The Bare Minimum I dug into struthless, a video-maker that Kyle follows, and found a lot of insight in his working methodology. I particularly like his DIY project board. Kyle and I were very taken with it, probably because our brains work in similarly chaotic ways, and we struggle to maintain focus on a single thread over longer periods of time. Avvai was more sceptical about its usefulness for her which makes sense since she is more innately organised than Kyle or I.

For Kyle and I it appeals for reasons of maintaining focus through visibility and accountability. Having other people be able to check in and see what we’re working towards, and interrogate that, even hold us to the flames, feels substantial. We’ll experiment with this project centric accountability in general, and visible progress boards specifically once we’re back in Vancouver.

Authenticity/integrity is something we keep coming back to

How can the creative process be shared, so as to dispel “the association of the creative act and the mythology of genius”, without devolving into a mere performance of creativity. Archetypes here might include,

• struthless, whose authenticity comes in part from his openness about his struggles (with drugs/alcohol, and with attention) but which is legitimised, given credibility, by his tangible artistic outputs.

• George Saunders’ effectively trying to write his methodology entire into A Swim in the Pond in the Rain, not holding anything back. Also see Annie Dillard,

  One of the few things I know about writing is this: spend it all, shoot it, play it, lose it, all, right away, every time. Do not hoard what seems good for a later place in the book, or for another book; give it, give it all, give it now. The impulse to save something good for a better place later is the signal to spend it now. Something more will arise for later, something better. These things fill from behind, from beneath, like well water. Similarly, the impulse to keep to yourself what you have learned is not only shameful, it is destructive. Anything you do not give freely and abundantly becomes lost to you. You open your safe and find ashes.

— Annie Dillard, The Writing Life, Harper & Row, 1989

• Joel Haver
  An independent director that Kyle follows who is both ambitious/prolific in terms of his output, and very transparent about the process and the funding of that process.

Filtering (media) as essential to finding meaning online

Avvai and I talked about media consumption, the potential for overwhelm, but also the liberation of realising that there is no need — and indeed, no possibility — of keeping up with it all.

Up until about 15 years ago a very online person could still more or less keep up with ‘everything’ happening online. What would become the major silos of the web launched to the public within barely more than a year — Reddit (June 2005), YouTube (December 2005), Twitter (July 2006), Facebook (September 2006) — but it was probably somewhere between the 2008 US presidential election and the early 2010’s that even the broad thrust of the online zeitgeist became incomprehensible to the individual. The world wide web had met it’s own Eternal September.

Though I appreciate why it can give rise to a certain dysphoria, I’m deeply optimistic about this ‘post-comprehension-internet’. Our one-time comprehension was a reflection of an insufficiently diverse landscape and, as billions of people came online and the web came to shape the real world, it was inevitable, necessary, that we would lose sight of its edges.

But how to cope?

The fire hose of media we’re confronted with today presses myself and others toward a kind of ad-hoc librarianship. A desire emerges to capture something irreducible from the mayhem in front of us. This is part earnest belief in its potential and part desire to assert control in a frenetic environment.
— me, Accumulation is not a substitute for creative work

Coping necessitates a system of filtering, efficient means of diverting the flood. Thankfully, us humans are well suited to this, this is what communities are for. A community is a system both for disseminating a set of ideas and distributing the work necessary to meaningfully pursue those ideas amongst an aligned group of people.

The great fracturing and (necessary) dysphoria within the online and IRL worlds over the last fifteen years or so, feels to me like the disaggregation necessary for a groundswell of meaningful communities.

Avvai and Kyle are relocating to Vancouver not arbitrarily, but because Vancouver is home to the highest concentration of their aligned community. And I’m relocating to Vancouver because Avvai and Kyle represent that alignment for me.

A sub-thread or corollary to this emerged later in the conversation, wherein I acknowledged that previously I had been closed off to certain ideas simply based on where they were coming from. For a long time I held onto a scepticism that reinforced the idea that books were the only truly credible source, but time and exposure has shown me that every medium — from water-colour to haiku, email to Instagram, pottery to photography, instrument to animation etc. etc. etc. — is fit to convey ideas, and that outmoded snobbery about origins makes the world much less interesting.

Self-confidence comes from living with integrity

One thing that I like about you Silas is that you are pretty offline, but when others talk about Instagram, and making videos etc. you’re not judgemental, you don’t judge people for that.
And with money too. You choose not to make a lot of money, but you’re not poo-pooing people who do want to make money. I like that.
— Avvai (paraphrased)

I’ll call this out because I think my journey on that front might be useful to certain people. I used to be what can only be described as super judgemental. About everything.

I used to judge people for the way they talked, dressed, looked, walked; for the music/films/television/video-games they liked or didn’t like; for the god(s) they believed in; both for being confident and for having doubts or being afraid (I was afraid a lot); and for just about anything else you can think of.

So this is bigger than Instagram or TikTok or tastes or fears.

Over the last few years I’ve become confident in my self and the things I’m doing in my life, so the insecure impulse to both withdraw from the world, from people, and to harshly judge all that enters my orbit has lifted. I do still wrestle with old habituated prejudices and assumptions about people, but on the whole I’m able to simply be myself and let others do likewise while those last vestiges continue to fade.

I think I’m still in the window where I can speak most usefully about this growth, because I’m still within it. The core of this growth has come from completely outside of me, from wiser minds met along the way. Several of those minds (and the faces in front of them) get a mention in Avash, avash, but no such list will ever be complete. At the very least, Jess, Avvai & Kyle, and the whole Siemens clan belong on it also. And a few hundred other characters too, most recently Srmi from Tunisia, Ferdinand from Germany, Sandro from Portugal, and Dani of Canada.

Which is to say that I believe self-confidence comes from hearing other people’s stories and sharing our own story first hand. There is no substitute. And the confidence to share our own story comes from living a life that we ourselves find interesting, to openly pursue the things that excite us without concern for other people’s judgements or misunderstandings. To live with integrity. Do that and the whole world opens itself to you.

Integrity brings us into proportion, allowing us to admire others and ourselves. “The first step is to realise that one is proud”, then to understand that “humility is not thinking less of yourself; it’s thinking of yourself less, finally allowing us to rediscover humility as “the spur that prevented a man from stopping; not a nail in his boot that prevented him from going on”.

Time boxing

Kyle finds time-boxing incredibly useful, where time-boxing might be expressed as setting a discrete goal and running with it for a set period of time.

Time boxing can operate a different scales.

Kyle predominantly uses time boxing at the scale of the day, or perhaps even the hour. In Istanbul he introduced me to the most dangerous writing app, which proved to be an almost super-effective tool for getting the first version of a thing written. I liked it so much that I made my own clone of it here.

Craig Mod talks more about time-boxing at the scale of months or weeks — explicitly time limited projects. He’s run a number of pop-up newsletters over the years (see Pop-Up Newsletters are the Greatest Newsletters) and uses these as a forcing function to create at a velocity — multi-thousand word photo essays every day — that he wouldn’t find sustainable year round. He also adopts the practice of Progressive or limited disclosure/exposure.

Progressive or limited disclosure/exposure.

Joel Haver, Andy Matuschak, and Craig Mod et al, all run membership programs for that subset of their audience who are really invested to be able to see deeper behind the curtain. This liberates them from having to polish their every output to the degree that people have come to expect of their public outputs. It invites a core group into the creative process, provisioning a space to iterate on ideas in a safe environment, while still being able to gather feedback throughout the process.

How to write in such a way as to be maximally useful

A big theme for Kyle over the years, across multiple projects, has been connecting people with their own stories, for their own benefit.

He wants to explore this again in what he’s calling The Very Inspiring Person Project.

This resonates for me with my practice — inspired in part by Andy Matuschak — of attempting to synthesise toward the irreducible. What is the kernel of the idea, the pure meaning. Examples of my attempts at this,

• Effective collaboration builds on a foundation of alignment
• Accumulation is not a substitute for creative work

But I also think I’ve gone too far away from story. Over-synthesis can leave us with not even enough to grasp hold of. Kyle’s strong sensitivity for story is a good reminder both that story is everything, and that the best ideas have already been written; our job is to re-contextualise them for our time, for our communities.

I would summarise this style of writing as an attempt to present ideas, concepts, archetypes (a person who quintessentially embodies a way of being), in ways as to be maximally useful. Developing that into

• Don’t bury the lede
  As early as possible, give the audience everything they need to decide if what you’ve created can be useful to them. This begins with the use of highly descriptive titles, but extends all the way through the work. Incomplete expertise or understanding should be acknowledged early.

• As simple as possible, but not simpler

  It can scarcely be denied that the supreme goal of all theory is to make the irreducible basic elements as simple and as few as possible without having to surrender the adequate representation of a single datum of experience.

— Albert Einstein, On the Method of Theoretical Physics, Oxford University Press, 1933

• Written for the author first
  Too many good ideas are made useless by a desire to make them palatable to a broad audience. What you’re writing should be maximally useful to you first, only then should careful affordances for an imagined audience be made. This is powerful because it is the only guarantee of a piece of work being useful to anyone, but also because it acknowledges that the people we are best equipped to produce meaningful work for are those with whom we already have a rich set of shared concepts/ideas/beliefs/experiences.

• Situated within a growing graph of ideas
  Any one artefact within a corpus of work should be fit to function as a leaping off point into the whole, but also into the context in which it has come about, by being highly referential. This is the mechanism for creative humility. Hypermedia offers tools uniquely and richly suited to this, but it is possible anywhere. Academic citation has stood as the ur-example, but such acknowledgement ought to be practised everywhere.

• Useful as a springboard for creative work, not as a substitute for creative work

A system for surfacing connections

I aim to create a system in the spirit of Niklas Luhmann’s slip-box and Vannevar Bush’s Memex (as described in As We May Think, July 1945), and get it into Avvai and Kyle’s hands.

I still have no idea what it even is
— Kyle

I’ve been doing a terrible job of communicating just what the heck my document system is for. Perhaps I’ve inadvertently made it seem more complicated than it is by focusing my description of it on how it works rather than on the more interesting why?

So here’s the pitch,

To achieve that, the system must support referencing (quoting, linking, citing), enriching (annotating, connecting), synthesising (identifying the irreducible), and creating (mutation, iteration, re-transmission).

Well, what’s wrong with a pen and paper, or a Google Doc? Why do we need a whole new system for that?

You don’t need this. I don’t need this. Nobody needs this system. But I want it. I know that my fickle memory and attention often prevent me from making substantial contributions to my areas of interest, and I believe I’m not the only person experiencing this. I believe deeply in the largely unrealised capacity of systems and machines (computers) to augment and assist our thinking.

I also believe that I can make a novel contribution in this space by focusing on the primitives necessary for specific contexts of use, rather than diluting everything down to the general case. I see the imperative that tools must generalise as a deeply entrenched and harmful pathology in the computing world. Generalised systems force users to contort themselves to insufficiently expressive paradigms and primitives (see We shape our software; thereafter our software shapes us for some of my prior thinking here).

Presumably man’s spirit should be elevated if he can better review his shady past and analyze more completely and objectively his present problems. He has built a civilization so complex that he needs to mechanize his records more fully if he is to push his experiment to its logical conclusion and not merely become bogged down part way there by overtaxing his limited memory. His excursions may be more enjoyable if he can reacquire the privilege of forgetting the manifold things he does not need to have immediately at hand with some assurance that he can find them again if they prove important.

— Vannevar Bush, As We May Think, The Atlantic, 1945

Kyle is most interested in a system that can surface connections between previous writing and references.

This clear focus has given me the lens through which to explain the system better. This, the surfacing of connections between things, is basically the entire purpose of the system, I’ve been getting bogged down in trying to explain related concepts. Ultimately, through a combination of machine assistance (embeddings etc) and human curation, the system should itself become generative — the goal is to support creative abundance.