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I think you need to pick things that you can deal with going wrong that wont destroy your life and have him do them and allow the consequences to happen. If he has no consequences that affect him he knows you will always swoop in and rescue him. What do you do for him that would make him uncomfortable or notice if it didnt get done that you could allow natural consequences take over?
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"I carried a watermelon?"
President of the no F's given society.
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