My first week of studying Italian did not yield what I had expected. I amassed a lot of material but I didn’t bother to actually go through it and try to see how appropriate it was for me. What I found very quickly was that my normal go-to resources were holding me back and that after just a few days of figuring out some basic verbs, pronouns, and tenses I was able to understand about 90% of what I was hearing and reading. Of course, I still cannot produce language at this level, but I had seriously underestimated my advantage in already speaking two other Romance languages and having studied Latin.
Because of that, I have abandoned my initial plan and I am starting to work with resources that are in Italian only with no English at all. Users on the Italian Language Learner’s subreddit posted some resources that I have really been enjoying. One is an Italian language video course that is only in Italian, called One World Italiano, and an Interesting site called Italiano Automatico. The thing I enjoy about this is that it’s all about providing comprehensible input to learners so you will find YouTube videos with subtitles in Italian. The author creates two videos with the same content but one spoken at a slow pave and the other ate a normal pace. The idea is that you listen to them multiple times until you can understand about 70% or more of what is spoken and then you move to the fast video. By repeating this sort of study on a daily basis you should be able to really increase your listening comprehension as well as improve your output because of repeated exposure to conversational Italian.
In the end, I’m still working with Assimil but I have added those additional resources and dropped the Pimsleur material. I’ve also added a few workbooks from the Practice Makes Perfect series such as the Sentence Builder and the Pronouns and Prepositions book. At least on the surface level after one week, I feel like the main barrier for me to have successful output in Italian is knowing how to use the prepositions and the pronouns as there are some important differences from Italian and Portuguese. I’m able to pick up the grammar quite quickly from reading and listening. But those books really seem like they are going to a great help. I've also joined the iTalki language challenge and if you are working on learning a new language in 2015 there is still time for you to sign up. It's a great way to stay motivated and earn some extra iTalki credits for lessons.