> You can remember them. You can avoid the search engine step. No need to search when you already know the answer. Which means…

You don't know what you don't know. Discovery is about leveraging common heuristics. The more context information that's available, the easier it gets to get to the answer. Giving the least amount of information runs counter to that.

A URL is a reference, an identifier, that uniquely references a resource. A search engine essentially captures a ton of context information that you can leverage to get to a set of relevant references. An identifier can be a meaningless string of characters - e.g. a UUID - and as long as it's accompanied with context information, you can get to the resource it references.

Conversely, if you capture context in the URL itself - meaningful words, dates, authors,... - you're actually providing a breadcrumb trail for visitors - people and robots - to follow, leveraging common heuristics they might use to get to that web resource directly. Might, because discovery is always a process of making educated guesses and following cowpaths to get to the right answer.

So, no, making URL's shorter isn't necessarily advantageous.

In the same vain: long passwords using commonly, easily to remember words instead of an unintelligible string of 16 characters.

Tangentially, I also have ambiguous feelings over the widespread use of URL shorteners. Partly because they act as a middle man providing brittle URL's that can - and will - break in the long run. Partly because they hide a ton of potential context information that might be captured in the original URL.

> You can tell someone. You can even say it out loud! Whether answering an email or talking to someone on the phone, I can say, “Go to sive.rs/ff for my talk about the first follower.” or “My newest book is at sive.rs/h.” I do this often, so having memorable URLs saves me a lot of searching.

Again, context matters. This might work if you want to highlight specific content - e.g. a marketing page for your book - but it certainly doesn't work all the time for all your content. Is that blogpost from 2007 really that important that you need to be able to "say it out loud" to someone on the phone today at any moment?

Short URL's come at a cost. What's the trade off you're making here?

> They look nicer. They’re aesthetic. They show care.

I don't care. Really. I don't. I care about readability and accessibility. Sure enough, URL's with tons of non-nonsensical query parameters are a blight, but this has more to do with readability then "aesthetics". It's an URL, not poetry.

> They remove the middle-man. With long URLs, people use those ugly social share buttons that promote (and further entrench) harmful social media sites, and add visual clutter to your site. Short URLs encourage people to copy and paste the URL directly, which lets them share it anywhere, instead of only the sites for which you have a share button.

Or maybe the answer here is to avoid using social share buttons on your website at all?

> They’re enough. Using 36 characters (a-z and 0-9): 4-character URLs give you 1,679,616 (36⁴) unique combinations.You don’t need more than that.

Well, how about "sive.rs/qxfa" or "sive.rs/kxig" or "sive.rs/ddiz"? It's an argument that's in direct contradiction with the author's first argument. Again, heuristics matter. Readability matters. A big chunk of those 1.6 million odd unique combinations aren't usable of the bat because they are simply unintelligible strings of characters without meaning.