In this article, the authors share the skills required to plan and execute a successful days-long backpacking trip, which they have discovered are also useful in advising student leaders. The authors' lessons were originally learned while backpacking with several friends. The six of them had planned and trained for months to do a six-day, 50-mile trip. Despite their best individual and collective efforts at preparation, one of their members suffered severe pain from an injury that predated the hike. Reticent to spoil their adventure, their friend chose to keep quiet about the discomfort. On the last day, when their friend's pain became too unbearable to keep secret, the final seven miles turned into a slow, challenging slog for everyone. As they redistributed gear to allow five to carry the load of six, their planned four-hour hike became an eight-hour crawl. What they had imagined to be a triumphant finish to a challenging journey turned into a stressful and exhausting end to their trip.