It's easier to get rid of things when you're giving them to someone who can use them, but don't let this kind intention become a source of clutter itself. I have a friend who has multiple piles all over her house, each lovingly destined for a particular recipient.
They say that people teach what they need to learn. By adopting the role of happiness teacher, if only for myself, I was trying to find the method to conquer my particular faults and limitations.
When we're trying to form and keep habits, we often search - even unconsciously - for loopholes. We look for justifications that will excuse us from keeping this particular habit in this particular situation.