Join Carl as he shares a story from his early days of backcountry skiing, reflecting on the blurred line between good decisions and fortunate outcomes in uncertain environments. Recounting a risky adventure down an avalanche-prone slope, Carl explores the concept of "wicked learning environments" where feedback is delayed, infrequent, or inaccurate, leading to a potentially dangerous reinforcement of erroneous behaviors. Drawing parallels to financial decision-making and personal experiments, Carl offers insights into navigating uncertain terrain and recognizing the true nature of the environments we operate in.