Using a qualitative study, two teachers, Emily and Rebecca, who started their teaching careers in their forties were interviewed and followed for 3 years to document their experiences in the teaching profession. The tale of these two teachers includes their joys, frustrations, and problems that surround their lives as middle school math teachers. Discussing such topics as, college preparation, isolation, time required, extra duties, little respect for teachers, resistance to innovation, and the need for a mentorship program, Emily and Rebecca honestly paint a self-portrait that includes the influence of their past experiences before becoming a teacher and the reality of joining the profession of teaching. All administrators and educators should take note of Emily and Rebecca's tale in order for changes to be made that will create an environment that is encouraging and inviting for all teachers that will lead to teacher retention, and, in turn, focuses on the success for all students.