Here wa my roadmap:
(1) I first learned assembly by learning computer architecture from Tanenbaum's book -- Structured Computer Organization -- and related course at the Vrije Universiteit Amsterdam. This taught me a toy architecture (Mic1) but it give me a rough idea of how assembly worked.
(2) Then, later I took a course in binary and malware analysis and all that we were required to do was to read x86 assembly in IDA and interact with it via GDB -- and using the command: layout asm, which gives a layout for all the register values and upcoming instructions.
And once I have a debugger available and understand it well enough, I can learn quite well since I can make little predictions and check if they are right or wrong, and so on.