1. In the situation where your results do not match your intended outcome, then you feed the learnings back into the cycle and have another kick at the can.
means: another opportunity. It's not a very good choice of words, however. Could have used: "another run at it."
2. Her desire to be happy is her real wanting.
Does this mean "her desire to be happy is what she really lacks, or what she really wants"?
Could be either meaning. The context could give you a clue.