I wish that it was more obvious when you forgot to do some things that could lead to a game-over. For example, I forgot to pay Chris on a Friday, despite having gone to the club. I went to see him on Saturday, I went to see him on Sunday, neither time did it give me the option to offer payment to him. Come Monday, I was greeted with a Game Over screen, and not sufficient backlog to reverse my steps to get back to a point where I could fix my error. This lost me something like two and a half weeks of progress and an hour or more since my most recent save.
An example way to handle it would be that, upon leaving the club on Sunday without having paid, Chris grabs the player character, abuses her, and demands that she pay an additional 20% in interest (or $600) for not having proactively offered the money on Friday. Alternately, you could allow the payment to take place on any of the weekend days before it triggers a game over, or trigger the game-over after leaving the club on Friday, or some other idea that you can come up with (root is a far more creative and better writer than I am). The current mechanic only offers frustration and no real emergent challenge, especially when you reach the point at which you're trying to blitz through days to progress with one of the long event chains (such as trying to get information out of Tony at his home during the week).