What's My Purpose?

This is the first question I ask myself when starting a painting or drawing.  You can't make intelligent decisions on a painting until you've decided what you're trying to accomplish, and have some idea of how you're going to accomplish it.  That may sound simple, but there are several facets to this idea and you should be able to answer most of the questions below BEFORE you start drawing/painting:

Audience:  Who am I making this for?  Am I trying to make something that my audience feels more comfortable with, or something that feels more innovative and new?
Some audiences are inherently hard to please and have to be
won over.  Like hipsters, unless you're Wes Anderson.

Format:  How will the audience experience this image/character/environment/etc.?  Does the format affect the scope of what I can communicate?
Fringe's mad scientist is a great character that probably wouldn't work in a video game.
Or in a stand-alone illustration.  Internet images have a unique format problem also:
everybody sees them at a different size!

Purpose: What needs does this painting/character/environment need to fill?  Are there special or arbitrary parameters from the publisher/art director/marketing/writers/technicians/etc. that need to be included?
The house in UP had to function as an interior and exterior
environment, hold a storehouse of props, work as a vehicle,
and be something audiences came to care about as a symbol
for Carl's deceased wife.

Story (technically an extension of purpose): What role does this character/environment/etc. play in the property?  What emotional chord do I want to strike with the viewer?  Are there additional story/moodsetting things I could layer into the piece without distracting from the primary purpose/story?
Jack Sparrow's costume design is great---an iconic "first read," with lots of
suggested history in the details, yet all of it supports his personality
and the core idea of his character.  

Premise:  Which of the many ways of expressing the above purpose and story will feel most fresh and interesting to my audience?  Is there a way of integrating the publisher's/art director's/etc.'s parameters in a way that "feels right" or gives things an unexpected twist?

Let me reiterate what I said earlier but add something:  If you can't answer all of the above questions, DON'T START PAINTING UNTIL YOU CAN.  In fact, if you can't answer them in a way that makes you feel inspired about your illustration or whatever you're working on, I'd recommend that you either do some brainstorming or start over with a drawing that inspires some of these things!