Should i put my current occupation even if i'm filing for a job that i no longer do? or should i put my old occupation. Do i need to also file these two w-2 separately?

You enter the W-2's separately but on the SAME tax return.  ALL of your income must go on the same tax return.  Do not file W-2's on different tax returns forms.

Put your current occupation into TurboTax.  This does not affect your tax return! 

You can enter multiple W-2's into TurboTax.  Some W-2s can be imported; OR, you can type them in yourself.

Click this link for instructions on  How to Enter More than One W-2 .

[Edited 03/20/2020 | 7:55 PM]