First Try Skynet... How Can I improve?

[nilamo]

It's AN option, not the only option.  And, in my opinion, it's the worst option.  A better option would be to wrap all your code in a function, and then call it.  When you want to quit, just return instead.

def main():
    while True:
        keep_going = input("Keep going? ")
        if keep_going.lower() not in ("y", "yes", "1", "true"):
            return

if __name__ == "__main__":
    main()