After a personal crisis shook his confidence in himself, Ben Pink Dandelion considered seriously the spiritual meaning of "confidence" (literally, to live and act "with faith"). His reflections led him to delve more deeply into early Friends' understandings about spiritual growth and religious development, and to apply those principles to the community of Friends as we practice our faith today. His insights are especially meaningful for liberal Friends, individually and as a society, as we look toward the future. This essay is based on Ben's 2009 FGC Gathering address and a subsequent presentation at Pendle Hill. Discussion questions included.