When using digimodes you have to rely upon another amateur who can tell you if you signal is being over-modulated. Or, as per my previous blog entry, look at the ALC meter on the rig.
Another way of doing it is by using another computer in the shack (everybody has an old one!) and logging onto a Web SDR receiver somewhere on the internet.
There are many now and a quick search on Google reveals where they are.
Install Ham Radio Deluxe onto the old PC and set it in demo mode so you are only controlling a demo radio.
I found a piece of shareware software called Virtual Audio Cable that runs in demo mode.
Download it from here
Install it and launch the Audio Repeater part of it.
Set this to take the output of your audio card and feed it to the Virtual Audio Cable 1 as per this picture