It's actually super easy and, atleast for me, was always intuitive. Most USB cables have their logo or something else engraved on the "top" with the air gap. And since the ports are mostly arranged the same way, there is rarely any problem. Maybe I am just too dumb to understand jokes, but it always confused me :(
I can't find a reference now. But from what I remember the logo is supposed to be on top facing the user when plugging a device in. This was part of the standard that defined the size/shape/etc of what USB is.
People don't always have perfect sight, lighting etc to see it. Or know about that tip. Or remember what it signifies. Often you're fumbling, doing 2 things at once.
I was ecstatic when I learned this piece of information a few years ago, and find it very useful when I'm able to use it. But I've come to learn that at least 50% of the time they either have no logo at all, or have something engraved on both sides in too small a size to be unambiguous. USB multiport hubs, mobile data cables, a lot of these little cables still need the 3 step process.
It's really only the sideways ones which give people trouble. Especially if it's sideways on the back of a computer (or tv) so you can't really see what you're doing).
Desktop computers are fairly easy too. The vast majority of towers have the motherboard on the right-hand side, so that can be treated as the "down" direction USB-wise.
Intel added the satiric text about the rule with double-tongue depiction in one of their whitepapers around USB3 publication for a reason. Sadly couldn't find it.
