In as much as you want to prepare very well for every enterprise you want to step into, you really do not want to over analyse and fall into the state known as analysis paralysis.
Analysis paralysis is when we analyse a situation so much that we then fail to proceed because we are simply overwhelmed by the amount of information we have uncovered.
It is definitely terrible to venture into any enterprise without some research and preparation. However, it is also not productive or useful to do so much research that you finally never set out due to over analysis.
The truth of the matter is that: preparedness can only take you so far, you must be ready to take leaps of faith at every turn.