I think the way to go about it is read some books gradually on history of computing & the various designs and rationale that evolved over time. Consider these sources:
1. The Annotated Turing.
2. A History of Modern Computing 3ed
3. The ACM Turing award lectures
4. Theory of computation - Dexter Kozen
5. Coders at Work
6. Hackers: Heroes of the computer revolution
Additionally, you could subscribe to Communications of ACM, which is a computing oriented monthly magazine.
1. The Annotated Turing.
2. A History of Modern Computing 3ed
3. The ACM Turing award lectures
4. Theory of computation - Dexter Kozen
5. Coders at Work
6. Hackers: Heroes of the computer revolution
Additionally, you could subscribe to Communications of ACM, which is a computing oriented monthly magazine.