Adolescence is a time of great ferment and change. When messages abound that tell a young person they are not enough, they tend to concentrate their energies on being prettier, smarter, or more popular. What does this leave out? Kelly and Tom Shelstad offer wilderness programs and other activities that have proven to be of help to young people and their families as they traverse the treacherous waters from childhood to adulthood in a way that supports self-esteem and self-knowledge. Each wilderness experience includes a built-in “purposeful challenge” of alone time. This is a time without the “normal” distractions of our addiction to electronic input, friends, Facebook, Twitter, TV, or car. It is a time when the participant can start to feel bored. Tom describes this time: “When we start feeling bored we try to do something to distract ourselves, to not feel it. But, if we are willing to sit in those feelings, there’s much wisdom, personal understanding, and empowerment that arises from that level of self inquiry.” This conversation highlights the benefits of how the exploration of wilderness can shift the need for outside validation. It helps teens to be more confident in their own skin, recognizing their authentic selves from the inside out. They will have met the challenge and recognize themselves for who they actually are instead of who they put themselves up to be on their Facebook page, Instagram, or Twitter.