From my experience I would say you should always plan first. (I even plan my planning phase).
I assume you’re doing something like a GUI wired up via .aspx using the MVC model, maybe even the Entity Framework?
Web development like this can very easily get complicated once you start to build it up.
It is important that before you do anything you know exactly what it is that you are trying to do, this way you know when you are undershooting or overshooting your goals and whether or not the code you are writing actually fulfils the requirements.
There are many models which you can base your project development on, all of which loosely follow a sensible System Development Life Cycle in one way or another.
If you haven’t read up on the different development methodologies, here’s a site that will give you a good overview : http://www.itinfo.am/eng/software-development-methodologies/