Upside Investing treats investing in the stock market like playing the casino. When you are running the program in Upside Investing mode, you tell the program how much you currently have invested in stocks, how much you intend to add to your stock holdings through time, and when you expect to start and stop converting your stocks to safe assets.
The program then sets your living standard floor assuming that all your current and future investments in the stock market are entirely lost. But the program also runs simulations to show you the chances of different upsides -- different living standards above the floor -- once you start converting your stocks into safe assets.
This video uses are free (but limited) ESPlannerBASIC to illustrate this concept.
If the video does not appear below, you may view here: Upside Investing