The old Jacobs chuck on my lathe has been a bit of a hassle for the last few years. Yesterday I finally caved and bought a new chuck key.
What the heck was I waiting for? It was only $6 for a USA made version and its made the whole chuck feel like new again
Seriously, if you have to hold your chuck key at a specific angle to get it to engage or can only use it in one orientation it is likely worn out.
Treat yourself!