This document summarizes the ideation phase of a design thinking process to redesign the school-to-work transition. The problem statement addresses that career advisors need new approaches to address 21st century career realities as traditional methods no longer meet student needs. Several ideas are proposed, including extending state employment agencies into colleges to expose students to real-life careers earlier. Another disruptive idea removes career advice from colleges, which could make staff redundant but remove funneling influences on students. The favorite idea has employers sponsor career advisor training to keep them informed on latest HR trends.