Four teachers share the challenges they faced when creating and running outdoor-focused secondary school integrated programs in British Columbia, Canada. The five most common challenges were funding constraints, insufficient support from administrators and colleagues, time constraints, liability and risk management, and inadequate skills and qualifications. The teachers also share their strategies for meeting these challenges. It is hoped that this article will help teachers who are interested in starting their own outdoor-related integrated program be better prepared and thus able to make their own professional dreams a reality.