I know that planning is of the utmost importance, but how and what do I plan? What are some ways you get around the initial hump of game development?
If the goal of starting your first project is to learn, then you shouldn't necessarily concern yourself with a lot of planning. Just create a high level outline of what you want to build and start working from there.
Think of your project as an onion. You start with the core and you add more layers on top of what already exists as you progress through the development. Since this is your first project, I'd recommend developing through trial and error. See what works and what doesn't and plan for new things when you move from one iteration to another.
In my opinion, planning "as you go", as opposed to planning everything to the tiniest detail before you start, is a much more flexible (and thus, usually better) approach.