Am I crazy to consider leaving teaching?

Q: I’ve been an 8th-grade English teacher for 10 years in the same school. Some days I love what I do, but most days it feels stale, and I wish I were doing something different. While I’m sure that’s true for many people, I spend a ton of time mentally plotting my exit. In my fantasy, I land my dream job as a book editor in a more exciting city and get a total life do-over. In reality, I have family and financial responsibilities, and I’m not sure I could even get a job, let alone be successful. As it stands, I am a well-respected teacher with tenure, and I wonder if it’s crazy to even think about throwing it all away. Am I stuck?

A: I doubt you’re stuck, but I’m going to put on my counselor hat before I address your career question. You voice multiple concerns. You’d like to switch careers, but you also want to live in a more exciting city and get a life do-over. Since you’ll bring yourself wherever you go, it’s worth taking a closer look at your unhappiness. You won’t be any better off if you come up with the perfect solution for the wrong problem. What’s at the heart of your dissatisfaction, and can you incorporate any incremental changes before you leave the field altogether? It’s much more difficult to transition than to stay the course, so you want to make sure you carefully weigh all of your options.

Once you’ve addressed any noncareer-related issues, perhaps with the help of a therapist, consider the possibilities. Can you pursue professional development opportunities that would help you innovate in the classroom or mix things up by teaching a different grade level? Have you told your supervisors that you feel stuck? Since you’re a respected staff member, perhaps they could help you identify a leadership role that would stretch your skills and feed your need for change.

If you feel your current school is part of the problem, would you consider a transfer? You might like serving a different student population or working in a more urban school setting. By taking this step, you can determine whether you’re dissatisfied with teaching itself or with conditions in your current environment. A job is more than the work itself, and collaborating with new colleagues might be energizing on its own.

Don’t forget to address self-care. Do you exercise and get enough sleep? Are you in a rut in other areas? When was the last time you picked up a new hobby or traveled somewhere interesting or read a book for pleasure? Do you have satisfying relationships with friends and family? Are there any ways to satisfy your desire for adventure that have nothing to do with work?

Beyond your work and personal life, factor in your values. To address that third piece, I recommend the Personal Values Card Sort. The activity involves examining dozens of cards, each one labelled with a word such as achievement, adventure, autonomy, change, comfort, wealth, or stability. You first identify the values that hold the most meaning for you, then determine whether one decision more closely aligns with your ideology. This exercise can help guide your decision making.

At a practical level, you can test the waters without giving up your job security. Network and talk to editors to get a sense of their routine, the pressures they face, and whether you think the grass would actually be greener. You can take some baby steps, perhaps by signing up for a writing or editing course or by supplementing your teaching with freelance jobs. You may find that it doesn’t have to be an either/or proposition. This approach also will help you honestly appraise your skills, assess available opportunities, and determine whether you’d be able to meet your logistical and financial responsibilities if you switched fields.

After going through all of these motions, you may still want to leave teaching. I believe you can make the shift if you are patient, open-minded, and resourceful. You may find that you have more luck with book or magazine publishers that specialize in education and can capitalize on your teaching background. It also might help to cast a wide net and consider work at education-oriented organizations or publications. It may take some time to land your dream job, but you absolutely can take the scenic route and still reach your goal.

Have a question that you’d like Career Confidential to answer? Email to All names and schools will remain confidential. No identifying information will be included in the published questions and answers. 

PHYLLIS L. FAGELL (@Pfagell; is the school counselor at Sheridan School in Washington, D.C., a therapist at the Chrysalis Group in Bethesda, Md., and the author of the Career Confidential blog. She is also the author of Middle School Matters, available at

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