I may sound dumb

Just got the 1TB passport Essential SE USB 3.0 portable with a new pc puchase. I want to transfer a bunch of file and programs from my old pc to my new pc. How difficult is this to do, and can .exe programs be transferred?? Somebody please let me know. I know I sound dumb…but thanks in advance for your help.

executable programs can be transferred… but… installed programs cannot be transferred… well technically installed programs can be copied but… it will not run…(e.g. microsoft office, adobe, burning softwares) got the point?

so, exe files, installers, docs… you can transfer