This document provides an agenda and instructions for an expedition to Pearl Street in Boulder, Colorado to mimic the process used in the Houseless Project, which incorporates design thinking elements. It outlines the goals of conducting field work and observations, talking to people, keeping track of time, connecting with others, sharing stories, and trying new things before understanding them. Upon returning from the field work, it instructs participants to reflect on their observations and experiences. The document emphasizes reflecting on learning to cement it in one's mind. It provides prompts for participants to respond to and reflects upon with the goal of modeling behaviors to nurture in students.