Despite research examining why teachers leave at such high rates, the intractable problem of attrition persists. Recently, teacher preparation programs have reported lower enrollment trends, and K-12 schools have reported higher attrition rates. Considering that one critical component of the problem is retention, more work is necessary to explore the nuances of the career trajectory to better retain teachers. Drawing upon my 10 years of teaching, this study uses autoethnography to engage in this work. The findings point to potential courses of action that might lend more insight into the complexities of the profession to better equip teachers, better structure resources throughout particular stages of teaching, and better educate others to support teachers in their work.