Understand your role, and with each update add to the body of evidence that you’re a good steward in that role. If people want your updates, they’ve entrusted you with something– a successful delivery of a product or feature, investment capital, company budget, their reputation, something. Convey that you value their trust and take stewardship seriously.

This is a short post full of truly excellent advice.


If there’ll be one future lesson from Slack, it’ll be that it’s not only possible to lose your lead from competitors advancing, but by regressing yourself.

I think this is both true and generally good to keep in mind when running a product which competes with others.

Sometimes you succeed by just being a viable alternative when an incumbent shuts down, declines or otherwise becomes unattractive. Workplace is shutting down and ceding its place to Zoom's competing product. When Yahoo! bought del.icio.us, people fleeing the popular service's new owners turned Pinboard into a much more successful business. Various bad press for Dropbox created opportunities for the small Dropbox competitor I once worked at, etc.


If you keep your boundary-token budget small, and allow your developers to accomplish as much as possible while staying within a solution space delineated by a single, clean cognitive boundary, I promise you can innovate as much as you want and your operational costs will remain manageable.

Glyph arguing for "boundary tokens" over "innovation tokens".

One of the things that was good when I joined Shopify is that everything that could be done in Ruby was done in Ruby. Similarly at my team at Internet Archive, everything that can be done with Python is done in Python.

It truly might be worth using a "worse" tool written in a familiar language.


I've always been a fan of manual curation and the care that goes into maintaining a collection, but instead of subsidizing a streaming "collection" to fill in gaps, I've retaken ownership of the whole thing. This has been both limiting and empowering — I can't turn on a radio station but I can remember what's in my collection and what I want to throw on.


I've recently decided to stop reading The Conversation, after two consecutive posts were openly accusing Europe's investors of not doing enough to be more like Silicon Valley. I'm seriously confused: how can anyone really believe, in 2024, that their business model is anything close to being sustainable? The mental slavery that parts of Europe still seems to be having towards the rot economy fuelled by a type of capitalism not integral to the continent is truly bewildering.


We have tested and tasted too much, lover-
Through a chink too wide there comes in no wonder.
But here in the Advent-darkened room
Where the dry black bread and the sugarless tea
Of penance will charm back the luxury
Of a child's soul, we'll return to Doom
The knowledge we stole but could not use.


Let us become intimate with poverty, so that Fortune may not catch us off our guard. We shall be rich with all the more comfort, if we once learn how far poverty is from being a burden.


There are many catastrophe-class AI events that don’t require AI to kill us or otherwise impair our physical health. For instance, I expect that most humans would also consider it catastrophic if, say, AI grievously impaired our political system, our economic system, our popular culture, our intellectual development, or our emotional health. Those are all on the table too. And much more likely than literal annihilation.


After the second time, the venture capitalists began to believe that this was something that they had done on purpose, and could rely on. "Software is eating the world," proposed Marc Andreessen, who had parlayed his brief time building the first graphical web browser into a career as a sage among a set of people overwhelmingly convinced of their own importance.


If you ever read an article on a subject with which you have a lot of first-hand experience, you'll notice that they always get major things wrong -- basic facts, dates, names of people and organizations, the stated intentions of involved parties, the reasons a thing is happening -- things even a novice in the space would know better about.

It makes perfect sense, if you think about it, that reporting is so reliably unreliable. Why do we expect reporters to learn about a suddenly newsworthy situation, gather information about it under deadline, then confidently explain the subject to the rest of the nation after having known about it for all of a week? People form their entire worldviews out of this stuff.