2023 by the bullets


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!


Celebrate the van Beethoven guy

It’s Ludwig van Beethoven’s birthday. Here are a few ways to celebrate the old piano-biter:

  • small: try his other famous piano sonata, No. 8 “Pathetique”
  • medium: try the third movement of Piano Concerto No. 5 “Emperor”, wherein the transition from the slow/middle movement into the final/fast movement is a brilliant sneak attack
  • large: the pretty good (but mid-tier for Beethoven, IMO) Symphony No. 3 “Eroica” aka the one where he wrote a piece for Napoleon but got mad and renamed it at the last minute
  • extra-large: the symphony that changed the game, Symphony No. 9 (the Ode to Joy one)

Previously: Beethoven’s Symphonies No. 7 and 8 are top-tier, Beethoven’s symphonies visualized.


ui.land

ui.land is an interview site at the crossroads of design and engineering.

Rauno Freiberg:

Trying to create software with tiny details that feel exciting to build, experience, and remix. Ever discovered a website that you can’t stop playing with and obsessing over? You can just sense the thoughtfulness and quality.

Paco Coursey:

  • What we call a delightful user experience is just delivering a faster path to user goals.
  • You’ll never understand the challenges, tricks, and edge-cases of a note-taking app until you build a note-taking app.

Sam Selikoff:

The best interface is one that’s not there because the desired outcome has already been anticipated.


Notes on strategy and execution

Will Larson, How to Size and Assess Teams From an Eng Lead at Stripe, Uber and Digg. This pull-quote lead me through some juicy lines of thinking:

Inflection points are just sustained implementation of a very reasonable thing. Often, the role of the great leader is not to come up with a brilliant strategy, but to convince people to stay the course with a very basic strategy.

Leaders lead folks in exercising a plan or series of plans (i.e. strategy). Basic strategies are almost certain to outperform complex strategies. Complex strategies tend to leak energy and effort at the seams between the basic/legible parts and all the edge cases and exceptions that generate complexity.

Read More →


Organize for Discovery

S-tier programming skill: organize code and behavior such that others can discover and understand it out later without your presence/consultation.

S-tier writing skill: organize a story or idea within a story such that the reader understands or builds upon it, makes it theirs.

A-tier relationship skill: organize or set stuff down such that your partner can find it later, without needing to ask you where it is. (Riffing off Merlin Mann here, I think.)

Ergo: organizing, and empathizing, are skills worth developing.

Read More →


Sidestep process by sharing tangible progress

Nat Bennett:

Cannot overstate the value of regularly delivering working software.

My single most effective software dev habit is to start with a walking skeleton – a “real” if very stubbed out program that can be deployed on its real infrastructure, receive real calls, visited for real etc. – because of what this does for non-programming stakeholders.

When they see a real working thing and then they see that thing get meaningful improvements they tend to chill way out and get much easier to work with.

You can save a week of effort on process with a couple hours of sharing tangible progress.

Related: you can save a week of planning with a couple hours of programming. You can save a week of programming with a couple hours of planning.


Notes on focus

I’ve tried a bunch of things, over the years, to find time and discipline to focus on working the tasks and projects that are meaningful to me. Mostly it boils down to actually doing the work and choosing the right kind of work. 🤷🏻‍♂️

Read More →


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!