It's hard nowadays. Maybe it always was. But it seems that bringing up the possibility of becoming a Sister is met with so much disbelief and opposition ("Are you CRAZY?!?) that it is terrifying to think about talking about it. And of course, if you say something to a priest or a Sister, it makes it so real - like you have already decided to take the step - that that is even more frightening. When girls and women talk to me about it, it is almost like they are confessing to a crime. "I think I might have a vocation." It's on the level of terminal disease.
It does not have to be that way. And for those who are thinking about it as a possibility - and that is where it always starts - find someone to talk to. Preferably someone who knows what she (or he) is talking about. Many priests do not have a great deal of experience with religious life. They may know one or two communities, but most have not had extensive experience. If they are lucky, the have resources to which they can refer women.
Good options are vocation directors of communities. Of course, they tend to have a lot of experience with their own spiritual family, and limited knowledge of others, but there is a good deal of networking going on out there. Often too, the diocese will have someone on staff who has access to information about religious life.
There is the Internet. I thought that was a great resource, but as I meet with girls and women I find that the amount of information is overwhelming. There's too much to digest. "I think I might be called - how do I figure out which one of the three thousand congregations listed is 'for me?'"