I'm currently in a similar situation, I want to see how far and how quickly I can take my ideas, in my personal time, while keeping a comfortable day job. I th

I'm currently in a similar situation, I want to see how far and how quickly I can take my ideas, in my personal time, while keeping a comfortable day job. I think there are a lot of variables involved, such as how much you value your current job vs. your passion and belief in the product you're personally trying to develop, as well as how much technical expertise you already have in the problem domain. There may never come a time when I feel completely comfortable with the thought of losing the day job, but this makes the most sense to me right now. Good luck!