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.
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.