This research aimed to understand how today’s teachers, operating in an exploratory context, experience the teaching profession over time. The findings reveal that these three teachers' experiences highlight the ways in which they continue to use their instructional skills for the benefit of others. After leaving the classroom, all three of these former teachers found that a career transition out of education was not as seamless as anticipated. These teachers each found that their detours through the classroom had concrete professional, financial, and emotional costs in the form of delayed entry into new careers, tuition costs, and daily struggles. The author concludes that this study identifies concerns about the costs for the teachers themselves while also recognizing the transformative potential of former educators applying their skills throughout society in a myriad of ways.