What are your rabbit holes on the internet? (For instance, HN one we all share)

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Software Engineering Daily www.softwareengineeringdaily.com
The question isn't restricted to technology sites, but I'll restrict the context of my answer that way. I've struggled to find sites that are similar to HN. Subreddits are about the closest thing:

https://www.reddit.com/r/programming

https://www.reddit.com/r/coding

+ Numerous other subreddits for every language/technology.

I really wish there was something just like HN, but for videos (like hour long talks). Does anyone know of any?

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Wikipedia. I will often get there looking for something specific, and end up following multiple links, opening dozens of tabs and spending several hours reading about various topics.
For me it's https://en.wikipedia.org/wiki/Mathematics

I'm an engineer by schooling but I've worked as a quant for the past 10 years. This means that I know a whole lot of "applied" math but will get tripped up by the formal terminology used.

This usually means I google a term and end up on wikipedia, where learning that term leads me to realized I need to look up the formal definition of another term, rinse and repeat.

As an example from my browser history, I was just reading

https://en.wikipedia.org/wiki/Statistics

for fun which lead to:

https://en.wikipedia.org/wiki/Central_tendency

which lead to:

https://en.wikipedia.org/wiki/Harmonic_mean

which lead to:

https://en.wikipedia.org/wiki/Arbitrarily_large

An idea that I will never implement is to create a mathematics wiki site structured as a "lattice", meaning that all links within a given explanation can only point "down", for suitable definitions of down. It's frustrating to try to learn anything from Wikipedia because it'll freely jump up to post-graduate math on any topic without warning. Despite it being suboptimal from a pure math perspective, I figured "down" would likely end up being "a topic covered earlier in the standard mathematics curriculum"; any other attempt to be clever I came up with always backfired for the "able to learn math from this resource" goal.

The second paragraph of the Wikipedia page on integers, about as simple a "math" page as I can imagine, as I write this, brings in "subset" and "countably infinite", and the third paragraph just goes off the rails if you're trying to use this to learn about the integers: "The integers form the smallest group and the smallest ring containing the natural numbers. In algebraic number theory, the integers are sometimes called rational integers to distinguish them from the more general algebraic integers. In fact, the (rational) integers are the algebraic integers that are also rational numbers."

I know enough of the relevant maths to actually perfectly understand that. I also remember enough about when I didn't understand the relevant maths to remember what it felt like to read stuff like that. My point here is not that it's a "bad page", just that it is very hard to learn anything that way.

This is exactly it. You want a directed tree for learning, whereas wikipedia is an undirected graph. Mathematics suffers the most since its tree is unusually deep, not wide.
My complaint about mathematics (and similar) articles is that they seem to be written for technical correctness, but not for instructional purposes.

So people who already understand the concepts can nod and agree "I find nothing (further) wrong with that," while learners definitely fall down a rabbit hole of successive links. At times it seems more like lawyering than teaching.

I've considered the argument that Wikipedia isn't meant for that purpose, that it's simply a repository for formulas and such, but I don't believe that agrees with any idea of human advancement and learning, and the site's own mission statement reads "to collect and develop educational content."

I for one, would find a lot of value in a mathematics encyclopedia slanted towards learning instead of mere technical correctness.

Wikipedia's physics articles suffer from the same problem.

Recently started to go to the library, any book, old, thin, large, is better than wikipedia for this.
On a more lighthearted note, I've given more time to slither.io than I would like to admit...
It's a great game to play locally on my phone, but I find the online version usually lags so much as to be unplayable.
http://tvtropes.org/ As an fiction writer wannabe, this site is both inspirational and disheartening. There are no new ideas under the sun but the variety and potential for new combinations is dizzying!

https://boardgamegeek.com/ All the information about boardgames you could consume in about four thousand lifetimes.

Matt Levine's Money Stuff: The further down the link stack you go the weirder it gets.

Slate Star Codex: A bit out of the mainstream, and he clearly has much more contact with people far, far outside of it.

I really enjoy Matt Levine's work. His articles on insider trading are simply some of the most enjoyable stuff I've read.
http://www.nakedcapitalism.com/ Economics/politics/finance blog by yves smith http://www.zerohedge.com/ Anti-establishment finance/economics/politics
I used to love ZeroHedge, but their signal:noise seems to have gone way downhill in the last year or two. There was always more than a healthy dose of paranoia and unconfirmed news, but it's gotten harder and harder to find the "good stuff".
imgur.com for random entertainment

Wikipedia about random subjects I come up with

reddit.com/r/arduino and related for project ideas

hackaday.com

Edmunds.com car reviews, at least when car shopping

Random sites on Wikia about TV shows or video games.

Compulsively reloading SO tags that I follow. Usually I can find questions I can't answer, which leads down the rabbit hole of learning it. Maybe I can even end up answering it by the end. win/win.
http://fanlore.org/wiki/

A wiki of nerd fandom stretching back to the 50s. I can spend hours just hitting "Random Article" and seeing the minutes of a meeting on Starsky and Hutch slashfiction in some hotel in 1978.

Twitter is a big one. Sometimes you just find that someone retweeted somebody else or that someone replied to them so you just peek into their page and you scroll down and occasionally find something interesting or funny; repeat until I'm tired of it.
I like to read the major online news sources from different countries and compare:

http://www.liberation.fr/

http://www.lemonde.fr/

http://elpais.com/

http://www.bbc.com/news

http://www.npr.org/

http://tass.ru/en/world

It's really quite surprising the differences you'll see as far as what is covered, how it's covered, and the placement & size of the articles. Not to mention of course the content & bias of the articles.

By combining the different views, I like to think I'm able to get a more complete picture of the "truth", although as you can see I read relatively left-leaning publications (apart from TASS, obviously) so that is not to say my worldview is completely fair and unbiased.

Other than that the usual techie stuff: ars technica, phoronix, nautilus, etc

http://tvtropes.org/ – click on the blue «Random Trope» button (or it is a pill? — a trope!) and get bogged down in interesting stuff about how stories are made.
news.rollc.at, my personal feed aggregator. It pulls most content from HN & Reddit, but there's also a bunch of random blogs.
I'm surprised no one has mentioned the Drudge Report. I'ts like Hacker News minus the comments, but for politics and also odd/unusual stories. http://www.drudgereport.com/
His ad networks have historically delivered too much malware.

We blocked it at work during one such episode many, many years ago, and got crazy complaints from the call centers about IT being part of a vast left wing conspiracy. Funny thing is that our boss was a county conservative party chairperson.

*faircompanies. Videos by Kirsten Dirksen (check YT channel "kirstendirksen".)
A few times each year I come back to Randal Munroe's "What If" [1]. By then I've forgotten where I left off last time and just kinda binge-read them over the course of a few days. If anyone here hasn't seen them yet (or, like me, hasn't checked in for some time), do yourself a favour and do it.

[1] https://what-if.xkcd.com