Given a rapidly changing labor market, advisors use parallel planning and alternative advising to teach students adaptability. Whereas parallel planning proactively prepares students for future transitions through considering multiple pathways, alternative advising occurs after students fail to make degree progress or secure admission and, consequently, must change their goals. This article integrates research that can help frame an advising curriculum, pedagogy, and learning outcomes as well as a case study that demonstrates such learning outcomes as coping with loss, managing anxiety, and restoring self-efficacy. Through the process described, students discover hope, resiliency, and a renewed focus on their goals.