If your brightness level is too high on your monitor, when you look at a file and go to tweak it you will adjust the brightness level in the file lower.How does the brightness level of the monitor affect the final image that goes out as a file to the web? It doesn't change it.
When the file goes out to the web, it will have a built in lower level of brightness.
So if someone opens up the file on their computer, with a monitor brightness set to a more standard level, the image will look quite dark.
That is what calibration is about - adjusting the response of the monitor (and video system) to look "normal", when the file is "normal".