Can we start a Google doc with potential questions for the quiz?
I think that this would be a great lead-in to the app that helps students stay on track for their college applications. So if after you completed this quiz, a list of potential schools was generated and students could select schools from their results to find information about. The selected schools, and any schools they want to add that were not on their list, could be added to their app so they start getting sent reminders about when application materials are due.
I think the program you're talking about is http://text4baby.org (I Googled it), and that's a great inspiration for the prototype! I think being able to personalize the app for each student's college application journey as well as providing general advice is an ideal combination. I like the idea of three messages per week (which is what http://text4baby.org does), it's not an overwhelming number so that you ignore it but it's enough that it keeps the application process on their radar. If one text was a general piece of advice, one was specific to their application, and one was a word of encouragement, I think that would work. There should also be access to further resources if students are interested. For example, if the advice text was related to how to write a good application essay, a follow-up link to articles related that topic or other resources, possibly even a live chat from college counselors.
I like the idea of a video game mindset (mentioned in the article Jenn posted), where students have the chance to try again if they don't accomplish their goal on the first try. It's is more encouraging and a concept that students are comfortable with based on their experience outside of the classroom. I'm not sure of where exactly, but I do know that this concept has been applied to classrooms before.
I also think it is incredibly important to educate the parents/guardians and faculty about the importance of letting their students make mistakes in a safe environment so that they learn how to recover from it before moving on to the "real world" where they could make even bigger mistakes. In the Cult of Pedagogy article about The Gift of Failure, she talked about a school making that book a reading assignment to families to help introduce them to the culture of failure.