How do people grind gears?

That's what I do, I only use light pressure when shifting and let the next gear engage when its ready to. Perhaps that's the reason I have never managed to grind, even the times I didn't use the clutch properly. From my understanding if enough force is used it's possible to push your way past the synchros and force the gear to engage (or attempt to) even if the speeds aren't yet matched. Maybe that's how people manage to grind modern synchronized transmissions

That's part of it, but some have underperforming synchros aswell. But YES, offer the gear stick up to the gear you want and when it's good and ready the gear will fall in.
 
Also, exactly how bad is it when someone grinds while shifting? Obviously it's not good and should be avoided at all costs, but is the occasional light grind something transmissions were built to tolerate to some extent or is it severely damaging?
 
The only manual I drive regularly is my MG.

I'm now on the 3rd transmission that's been in it in my ownership.

The first of those, probably original to the car, had a cracked 3/4 synchro, something that's at least somewhat common on the 4 synchro boxes and I've driven others with it. It would always grind going into 3rd unless I double clutched, and usually would(lightly) in 4th. That was one of the reasons that transmission was replaced, as non-OD boxes are cheap enough that most don't bother fixing them(the second was removed to fit an OD transmission that's in there now).

These boxes, like a lot, don't have reverse sync and they also don't have a lock-out other than a stiff spring. Getting into reverse sometimes is a fun dance of shifting into 1st or second and then trying reverse again. With that said, I've inadvertently ground reverse before in "spirited" driving where I shot right past the 1-2 gate and into the reverse gate.

Prior to 68, those cars also had non-sync 1st(usually called a 3 sync box), and arrangement I know was decently common on a lot of older 3 and 4 speed boxes. Those can be fun to get moving from a stop, although usually shifting into second and then immediately into first(clutch still down) will get them the first time.
 
Also, exactly how bad is it when someone grinds while shifting? Obviously it's not good and should be avoided at all costs, but is the occasional light grind something transmissions were built to tolerate to some extent or is it severely damaging?
depends how hard you're pushing.
 
L
Also, exactly how bad is it when someone grinds while shifting? Obviously it's not good and should be avoided at all costs, but is the occasional light grind something transmissions were built to tolerate to some extent or is it severely damaging?
The synchronizers get damaged and chipped bits and particles floating around in the transmission will cause wear and potentially damage bearings.
 
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