The document summarizes UNC-Chapel Hill's successful migration to the Sakai learning management system. Some key lessons learned included embracing the failure paradox, recognizing that change to software systems does not need to be as difficult as open heart surgery, carefully considering timing of announcements and rollouts, using data and reporting to show progress, and finding ways to delight users through small surprises. The migration was achieved through an emphasis on autonomy, humanity in interactions, evidence-based communication, flexibility, and making the change process enjoyable.