IMHO 1) Time to jump As long as you ask question "when should I do it", you are not ready. From my own experience,when you feel it, you know it is right time.

IMHO 1) Time to jump As long as you ask question "when should I do it", you are not ready. From my own experience,when you feel it, you know it is right time. That "feel" is a natural conclusion of a lot thinking, researching, preparing and prototyping. It is like you need to eat when you are hungry -- you will not ask "when should I eat" 2) Freelancing Start something takes a lot of time and effort. Freelancing may take your time and energy away. I did that trying to start something on the side, which I considered a mistake. BTW, are you hands on developer, or development manager? $300k for developer sounds high to me -- maybe you are super-star developer...