When we begin to set boundaries with people we love, a really hard thing happens: they hurt. They may feel a hole where you used to plug up their aloneness, their disorganization, or their financial irresponsibility. Whatever it is, they will feel a loss. If you love them, this will be difficult for you to watch. But, when you are dealing with someone who is hurting, remember that your boundaries are both necessary for you and helpful for them. If you have been enabling them to be irresponsible, your limit setting may nudge them toward responsibility.