Blogs were/are a fun moment

Manuel Moreale, Why I write:

But the reason why I started is long gone at this point. I started the blog as some sort of public accountability tool and it’s now everything but that. I don’t write to be accountable. I probably should.

Manuel asks a lot of folks about why they started writing their blogs. It’s a great question! Some folks want to get weird, others can’t not write and putting it online as good as anything, still others want to connect with a community.

That last one, connecting with a community, is closest to my answer. I started because there was so much excitement, energy, and connection in the early 2000s blogs. It was a real scene. And, plenty of invention! Before there was centralized social media and web 2.0 there was decentralized blogging. An earnest attempt to take the technology of peer-to-peer file sharing and build something besides music sharing on it. It was a fun moment.


Collective flow

Dave Rupert, Play at work:

I’ve talked about this before in the context of prototyping and play and how we worked at Paravel. It’s a lot like playing baseball; each member of the team showing up to practice, volleying work (in screenshots, short videos, or demos), pushing changes, communicating thoughts and challenges in the moment outside the confines of slotted meeting times. Me and my coworkers, having a catch.

Several years ago, when I was doing improv, I was rehearsing for a musical, of all things. At the same time we were getting started with table reads and gel’ing as a cast, two other shows were rehearsing in the same theater. One show was about to open, very much having their thing dialed in. Another cast was somewhere in the middle, having figured out what they were about but still trying to get the execution just right. Everywhere in the theatre, there was creation and exploration energy and it was one of the most awesome things I’ve done. This despite not liking musical theater much!


I don’t like the idea of “return to office” and I don’t think you could make it work anyway. The social momentum that kept a critical mass of people in one office has been broken, you can’t put that toothpaste back in the tube.

That said, I have yet to feel that same energy in remote work that I did in a local theatre on rehearsal night while various groups were making something together, in the moment, and iterating on it as quickly as they could share a glance or read through a scene.

I bet some teams have figured out how to feel this way in remote/async setups. But, it feels like most are still running the old in-person playbook that we learned, and sometimes thrived with, over the past years and decades of our careers.


Low-key tools-for-thought

I have an elaborate, perhaps baroque, setup of journals, notes, tasks, highlights, read-it-laters, feeds, and canvases-for-thinking. I consider it a crucial, and very idiosyncratic, piece of “knowledge worker infrastructure”. Furthermore, I don’t think I could handle a lot of the work and projects that I do, to the extent that I do, without it.

But, I hope that constructing such a scheme, and doing all the time intensive background research and tinkering, is not something everyone would have to expend effort on to think better and more clearly.

My hunch here is that the software bundled with iOS/iPadOS/macOS is very close to allowing folks who just want to remember and brainstorm get started immediately. Currently, a couple of elements are missing. This means you have to hit the third-party ecosystem escape hatch and consider a daunting variety of applications, workflows, and identity/quasi-religions.

Herein, a wishlist of system-level capabilities that would make macOS an even better “bicycle for the mind”.


In any old macOS app, I want to highlight text (mostly) with any pointer (mouse, stylus, finger) on any device (laptop, tablet, phone) and capture/promote text. I may want to add my commentary or notes too. Afterward, I should be able to search for this in Spotlight, at the least. Even better if the whole document/page/file/etc. the text came from is indexed, so I can find highlights despite imperfect memory.

macOS already extracts contacts and events from plain text. Faces are identified in photos. Why not make text excerpts/highlights/passages a first-class thing in the system’s information architecture?


I want to identify key ideas, concepts, people, and other nouns, so I can hyperlink between them and navigate them in something like the Finder.

This verbs-and-nouns concept was key to AppleScript. I’ve read that it was part of the conceptual bedrock of NeXTStep, but I haven’t found more than a few passing sentences on that.

Why not carry that idea forward or rediscover it on macOS? Some folks want to do more than scroll, post, and transact.


Notes and Journal, along with Finder and Spotlight, seem very close to checking all the boxes here. 🤷🏻‍♂️I don’t use those apps, so I’m wildly speculating here. Out over my skis, as they say. That said, this is so close to the core of what you really need to do next-level, thinking-augmented-by-computers.

Even though I use very particular apps, I feel like Apple has the right foundations here. A journal app for capturing ideas, reflections, and life as it happens. A notes app for putting structure and organization around the ideas that emerge from those moments. Tie it together with search to resurface and rediscover those journals and notes.

A fellow can dream, right?


iA Writer and AI

Writing with AI:

Writing is not about getting letters on a page. It’s not about getting done with text. It’s finding a clear and simple expression for what we feel, mean, and want to express. Writing is thinking with letters. Usually we do this alone. With AI, you write in dialogue. It comes with a chat-interface, after all. So, don’t just write commands, talk to it.

iA Writer’s integration is the first use of LLMs I’ve seen that I’d consider original. They didn’t slap on a chat interface where one wasn’t needed. It’s not autocomplete-but-smarter.

Instead, they show authorship/origin of text as either human or machine-generated. As you edit out the AI machine’s writing, the text visually and literally becomes more your own creation. You engage in dialog with the machine and use that to improve your thinking. The machine doesn’t think for you. Bravo!


Everything’s a draft

Publish pretty much everything you write because you can’t predict what is going to be popular. There is a lower bar for quality, but barring dishonesty and literally unreadable prose, everything else should go out somewhere. Incompleteness is no excuse. Publish the first part now and the other parts later.

– Kent Beck, Publish Everything

Get the idea out there, especially if it feels like there’s depth to explore but you can’t full traverse it in the moment. And, reduce friction to sharing the promising drafts!


You can’t read the whole internet, so put your energy into something that matters to you

Oliver Burkeman, Treat your to-read pile like a river:

To return to information overload: this means treating your “to read” pile like a river (a stream that flows past you, and from which you pluck a few choice items, here and there) instead of a bucket (which demands that you empty it). After all, you presumably don’t feel overwhelmed by all the unread books in the British Library – and not because there aren’t an overwhelming number of them, but because it never occurred to you that it might be your job to get through them all.

I like to think of it as the productivity technique to beat all productivity techniques: finally internalizing the implications of the fact that what’s genuinely impossible – the clue is in the name! – cannot actually be done.

You cannot actually read, process, and comment upon the whole internet, or even your little corner of interesting discourse. But, you can click “Mark All As Read” and move on. River-of-news style timelines automate marking items unread instead of automating bringing you the good stuff. Reeder and NewsBlur have options for it. I bet others do too. Reclaim your attention!

Unfortunately, most advice on productivity and time management takes the needle-in-a-haystack approach instead. It’s about becoming more efficient and organised, or better at prioritising, with the implied promise that you might thereby eliminate or disregard enough of life’s unimportant nonsense to make time for the meaningful stuff. To stretch a metaphor: it’s about reducing the size of the haystack, to make it easier to focus on the needle.

There’s definitely a role for such techniques; but in the end, the only way to deal with a too-many-needles problem is to confront the fact that it’s insoluble – that you definitely won’t be fitting everything in.

It’s not a question of rearranging your to-do list so as to make space for all your “big rocks”, but of accepting that there are simply too many rocks to fit in the jar. You have to take a stab at deciding what matters most, among your various creative passions/life goals/responsibilities – and then do that, while acknowledging that you’ll inevitably be neglecting many other things that matter too.

I’m guilty here! All the best in task management, getting things done, note-taking, journal writing, and even saying no won’t get the work done. I have to take the gift of clarity and focus generated by all these routines, and do that “big rock” important thing. I have to find peace with the trade-off of doing one thing instead of all the other exciting things.

Or, maybe generative AIs will provide Walt Disney-like agency to direct and sustain diverse projects outside my expertise with Imagineering-quality output. Wouldn’t it be nice!


Smaller barriers to entry, bigger possibilities

James Somer, A Coder Considers the Waning Days of the Craft | The New Yorker:

In chess, which for decades now has been dominated by A.I., a player’s only hope is pairing up with a bot. Such half-human, half-A.I. teams, known as centaurs, might still be able to beat the best humans and the best A.I. engines working alone. Programming has not yet gone the way of chess. But the centaurs have arrived. GPT-4 on its own is, for the moment, a worse programmer than I am. Ben is much worse. But Ben plus GPT-4 is a dangerous thing.

Simon Willison on the same:

I think AI assisted programming is going to shave a lot of the frustration off learning to code, which I hope brings many more people into the fold

We’ve entered the age of AI-powered coding, writing, speaking, and painting centaurs.

If we play our cards right, we will lower barriers to entry and raise the ceiling of possibility to new levels. If more people can create in mediums that are considered specializations now, that might open allow experts to go deeper in their specialization or branch out into areas that were inaccessible without compromising their specialization.

The idea of a dilettante, a person who cultivates an area of interest, such as the arts, without real commitment or knowledge, might become acute or obsolete. We might end up with a new level of “yuck that looks some amateurish and generated”. Or we might end up with reviews like “the artist deftly combines generated and hand-drawn sketches with procedurally generated music modeled on their own previous album I Play Pianos, By Hand, Like Duke Did”.

Of course, we’ve heard this story before and famed economist Keynes is (infamous?) for predicting mechanical automation would all have us exploring our favorite hobbies at this point. So, we gotta play our cards right.


Saying No is the first step

Ryan Holiday, 35 and 34, 36 Lessons on the Way to 36 Years Old:

As part of that, I made the difficult decision to call my publisher to push my next book a year or so. This was a massive clearance on my schedule—several hours a day did not have to be spent researching and writing on a project. Yet it was remarkable how little my life changed. Because tasks expand to fill the space, because it is so easy to say yes to other things. Less demands vigilance and discipline, perhaps even more effort than actually doing stuff.

The reward for saying no feels like saying yes to a more important thing. But you still need decision discipline after that first “no”.

Whenever I’ve heard things like “the key to serene focus and productivity is saying no more often”, it often seems like saying “no, thanks” on projects and potential work is the top of the hill. Like it’s all downhill to doing great work from there. Say no, they say, puts you on easy street to writing the great American novel/album/YouTube channel/large language model.

Alas, saying no is not one weird trick for exercising all of your decision-making and discipline in one crucial moment. Making great stuff requires many small moments of saying no. Say no to looking up that frivolous fact. Say no to the pull of social media. Say no to taking a day off your habit of making great stuff. Say no to that Oreo cookie. ☹️


Aristotle’s ethical means of virtue and vice but for creative work:

  • Winning is the mean between moving the goal-lines to finish and not finishing due to non-constructive goal-lines
  • Quality is the mean between piles of incomplete junk and one or two overwrought ideas
  • Taste is the mean between copying and invention in a vacuum of influences
  • Flow is the mean between distraction and idleness
  • Iteration is the mean between doing it once because you nailed it and doing it once because you gave up