The folks at Tenderness Gathering Place reached out to us to hold a retreat at their gorgeous Lunenburg retreat space, and we couldn't say no. Attendees had the option of sleeping over and continuing to better know each other, or staying just long enough for the structured activity. We designed a series of activities based in psychology research to help attendees rationally question their self-doubts and better utilize their character strengths. Those who participated in the activity reported greater clarity and confidence in making difficult decisions; deeper understanding of themselves and why certain events trigger emotional responses in them; and significantly greater coping ability in response to emotions that arose on a day-to-day basis. We drew on research about cognitive behavioral theory, mindfulness, and positive psychology for this event.