Loopholes are for assholes

When I was a kid, there was grown-up person I thought was really cool. One of the bits of ‘wisdom’ he shared was something like this:

You can park wherever you want. You can park right in front of the door of the store on sidewalk and walk right in. No one will do anything about it!

At the time, I though: Woah, this guy is a genius! He’s operating on another level!

Now that I’m the grownup, I think back on this ‘advice’ with sadness. This guy wasn’t a genius – he was an asshole (they can often look similar on the surface, especially to idiots).

In my short and incomplete stint as a post-secondary philosophy student, I remember learning about a simple way to evaluate a philosophy or worldview: Consider what would happen if everyone subscribed to that worldview. I’m probably thinking of Kant’s categorical imperative.

We can’t all park in front of the doors at Walmart – so none of us should.

 

Moats?

I love a good metaphor, but I’m not sure moats were as effective as everyone writing about AI in 2026 seems to think they were.

 

C Sweet

For more of my career than I care to admit, I thought the phrase “c-level executive” referred to executives who performed poorly (not like those A-level and B-level folks!).

I now know that the C stands for “Chief” as in, “Chief Executive Officer” or “Chief Technology Office”.

You can imagine how this led to some confusing conversations.

 

I’m a tax prude

Sometimes a contractor or service-provider will ask if I’d rather pay in cash. The implication is that a cash transaction can be done without tax – and either or both of us can “save” some money.

What’s not said, in these exchanges is: Hey, want to cheat on our taxes together?

No thanks. I’ll pay the tax. I enjoy the schools, the roads, public broadcasting corporation.

I don’t have some sort of extra-strong moral muscle. It makes me sad that people see the collective pie as something they can skim from, no matter how little the amount. It makes me double-sad that they assume others want to as well, because they’re probably right – others do want to as well. It makes triple-sad that some think you’d be a fool not to.

 

Golden Gate Bottle

Screenshot of macOS menu bar showing a batter icon that looks like a baby milk bottle on it's side.

Best new feature in macOS 27 (Golden Gate): A handy icon in the menu bar to show you how much milk is left in your baby bottle.

 

Former Latters

I’m an adult and have been for several decades. Every time someone say “it’s the former”, or “it’s the latter”, or “more the former than the latter”, I have to stop, and think: “Which one is first, former or latter?”

It’s not your problem, it’s mine.

 

Caring for each other, including the weakest in society, is a sign of strength

Jean Chrétien, former Prime Minister of Canada at age 92 (the quote is around the 11min mark, but the relevant section begins around 8min30s):

“Welcoming people from all over the world, [and] caring for each other, including the weakest in society, is a sign of strength.”

 

Modern Day Typographer

The Modern Day Typographer is impressive.

 

Retroactive Sentiment

If you enjoy some piece of media (a story, a song, an image), and then find out it was created with AI, is it reasonable to have your enjoyment impacted in retrospect? It sure is.

John Gruber wrote on his blog (that has a pretentious title, which I can identify with):

My advice is not to care whether anything was written by an AI or a human. The only thing worth evaluating is what we human readers are naturally good at determining: whether it is good or bad. If it’s good, read it. If it’s not, don’t. […] If you read something and enjoy it, and subsequently find out it was generated by an LLM, don’t feel bad. You read something good that you enjoyed.

If I read something, enjoyed it, and subsequently found it out was generated by an LLM, I absolutely would feel bad. To suggest I should not change my sentiment implies that text and reading are solely for the purpose of conveying some objective information.

I have at least one other purpose in reading: to gain a shared understanding with another person. I want to have a version of a thought that was shaped by another human, and know we both had our own version of this shared thought. It is this connection, not just the text, that matters to me. Also see: Text is a shadow of thought.

Imagine a person had ethical or religious reason to not eat meat – or even just a preference. Imagine that person enjoyed a meal and was then told: “Ha! That was meat and you couldn’t even tell!” Would you say all that matters was whether they enjoyed it or not?

 

Smashing Pumpkins Tribute for 2026

There’s a tribute album of Smashing Pumpkins covers that has some gems. Smashing Pumpkins were a formative band for me, and Siamese Dream and Mellon Collie and the Infinite Sadness will always be among my favourite albums.

Album cover with CD extending from it with an illustration of a woman with light coming from here eyes, and bats coming from her hands. Reads: A TRIBUTE TO SMASHING PUMPKINS SENDING HEARTS TO ALL MY DEARIES

A few tracks from this cover album I particularly enjoy: