how do I plan for a short film?

Understand that if this is intended to be a high end project, "planning a short film" is difficult. People go to school for this stuff. If you're just making some videos, write a script, plan your shots, and watch for continuity. A short film, on the other hand, there are multiple steps.

Your first step is to write a draft of a script. While this is for you, you're going to want to write within usual screen writing norms. There are programs out there that can help you format this. Your short film will flow better and be subliminally more engaging if you write in the convention of acts of Freitag's Triangle, as with any linear narrative.

Plan your shots. I know it can be tempting to set things up on the spot, but your production quality will improve drastically if you plan your shots (describe them as in depth, yet as simple as you can on paper) before shooting. This way, if a shot doesn't work, you have your planned description and you can tweak it and work with it to make it work. If you go in without a plan, and your improv plan fails, you're going to be left scrambling to get something pleasing.

Have a crew throughout. People to give feedback on scripts, assist on directing, manage continuity, etc. Finds actors. The whole deal.
 
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