Really, I think some sort of award should go to the inventors of the USB plug. It can only go in one of two ways, yet you (well, I) will get it wrong two-thirds of the time. How did they do that? And better still, if I get it wrong, and flip it over, it will still be wrong half the time. Amazing!
You techhie, you!
Dan
Relevant xkcd smbc.
I would like to introduce you to USB-C
I love USB-C. With the usual USB, with TWO possible options, it usually takes me THREE tries. At least.
Those are a godsend. I’m only 41, but I find it harder and harder to look at a mini usb and figure out which way it goes. In theory, the USB logo is supposed to face up or left, but that’s hardly always the case. It would be nice if that was actually one of the requirements to be USB compliant.
I even have one USB device that isn’t hot-swappable. It’s on a pin-pad for a credit card machine (this one right here). Unplug or plug in the pin pad while the credit card machine is powered up, even by accident, and the pin pad has to be replaced to the tune of about 200 dollars. For something that easy to wreck, I’m surprised they didn’t use a better connector. Either a twist-lock or even a small screw to hold it in. It’s not uncommon for cashiers to unplug it as they’re cleaning and untangling cords or even just by yanking on it a little too hard.
The inventor of USB-C should, at a minimum, receive a Nobel Prize for … something. Maybe a Nobel Peace Prize.
My usual process with the regular mini-USB plugs:
- Look at the outlet
- Look at the plug
- Orient the plug to the outlet
- Attempt to connect them
- Flip the plug and try again
- Repeat step 5 until connection is achieved
Yep, sounds about right.
Quantum physics governs the orientation of a USB plug. Typically the user tries to insert the plug, which won’t go in. The user then inverts the plug, which still won’t go in. They then inspect the plug to determine which way in it goes and then inserts it. It goes in. This is because the USB is in an indeterminate quantum state until directly observed. Prior to being observed, its state is between the two quantum states, known as wrong way up and wrong way down.
Most USB cables with full-size connectors have a USB marking on one side of the connector, which is good enough for me. Some, however, don’t (looking at you, Western Digital external drive makers!) and those who ship USB cables with no orientation markings deserve a special place in hell.
Even better than markings, especially for mini-USB, are connectors with a little depression on one side to help you orient it, even in relative darkness.
I mark the “up” side of USB cables (regular/mini/micro) with a dab of yellow nail polish. Vertical USB ports on my desktop/monitor are marked as well. I mark USB-C cables (both sides) with pink nail polish.
I always figured it stood for “Up Side-down, Buddy”
Yellow Nail polish???
I thought about either marking or some sort of stick-on thing, but I figured any marking would eventually wear off and anything stuck on would eventually fall off! 
USB-C now makes it possible to be unable to insert the plug correctly, remove it, then reinsert it without having to turn it over.
That right there is funny!!
“Uttha Side, Brutha”
They make an amazing range of colors these days. I have informed DH I draw the line at hi-vis safety orange. 
As to the OP, my older son’s friend has a theory that USB-A plugs are actually four dimensional. That’s why it can take three tries to go in, even though to us they appear to only have two major sides.
Well, better to use it to mark USB plugs than to actually put it on one’s nails
Which works if you only plug into one device, or all your devices have implemented the USB standard correctly. I however have several devices where the socket is upside down. Or that have sideways slots and whether the “top” is to the right or left is random.
I recall reading some wit’s comment that when the guy who invented the USB drive finally dies, at his funeral his casket will be slowly lowered into the grave, then pulled back out, flipped over and relowered.