Running a python program in order to log in to windows or mac operating systems

I have a little Python program that I wrote that prompts users to input a day of the week for a corresponding date that the computer randomly generates. It's a way for me to practice calculating the day of the week for any given date. The algorithm is essentially John Conway's "doomsday" method which he devised in 1970. I read that he is able to spit out an answer in under 2 secs. Apparently he programmed his computer to quiz him by having it prompt him to answer a few every time he logs in. How could I program my computer to do this? I have two computers, a windows and a Mac. I'm by no means a programmer, but I was able to program the doomsday method in python. I would now just like to have my computer run the program and give me 2 or three dates every time I log in that I would have to accurately calculate the day of the week in order to log in.