So why is the initial user experience always rough in self-designed products?

A big problem with self design is that it doesn’t deal with things that you won’t do frequently with the design. One of those things is using the design for the first time, because, well, you can only do that once.

You see this in a lot of self-designed products: the initial user experience is rough, never explaining why you’d use any of the key functions, and hardly ever giving the user a great way to get started. Because self-designers rarely are working from a blank slate, the initial process of populating the application with data is not as smooth as the usage patterns once you get going. The entire getting-started process is really difficult.

Great Read. Also, read this: Actually, You Might Be Your User.