A good way to understand the medium is the message is to to notice that many times the medium change is actually more important than the content. We often tell the same content over and over again while it the evolution of different media channels cause the greatest side effect.
One great example is the web. Prior to the popularization of the World Wide Web there was no mass media channel that was open to everyone. You did have lots of different mass media channels with TV, Radio and printed media being the most important ones but who could publish? who could broadcast? With the Web all of a sudden, everyone could and that changed the world. We still tell the same stories, take the same photos, the medium is more important than the message.
It helps to think of this in the context of the advent of radio. Before radio, getting information across vast distances was really tricky. If you were lucky, you'd have access to telegraph. Without it you needed the message to physically travel by mail, courier or someone. With radio, all of a sudden the world was quite smaller and this changed the world in a way that was unexpected. After that, we got TV, telecoms, internet, so we're used to drastic changes like that we seldon realize that medium change actually changes the whole thing as we're too deep living through these times.
Did it help?