Q: “I’ve been in my school community for several years now, and I’m considering my next career steps. When I started here, my goals were aligned with what we were doing, but now I’m not so sure. When is the right time to leave a school community and seek a new job elsewhere?”
Signed, A teacher looking for a new challenge
A: My first teaching job helped me become the teacher I am, but after three years, I knew that I had learned what I could from that environment. So, despite feeling responsible for my students, I decided to head to a different kind of school on Long Island, outside of the city, to see if it would be better. I found that the environment there didn’t suit me either. I learned a lot, but ultimately, it was not my forever work home.
From there, I took a position at a small, themed school, and it really seemed like this was the one. Everything was different from the way they went about hiring me to what the school day looked like. I thrived in that school for almost a decade. It’s where I was able to innovate and grow as an educator — to dream of a future that was different for students. It was the school that gave me room to grow into who I am now as an educator. It was hard to move on from this school, but I knew there was still more to learn, so I took a job as an instructional coach at a school in another city. It felt like the right position, but it turned out to be the wrong time. I took a leadership position closer to home so I could be available when my family needed me.
As you can see from my story, there is no single “right” time to leave a school community. For many educators, deciding whether to stay or go is personal because schools are not just workplaces — they are communities where relationships, routines, and purpose are built over time. If you’ve spent several years in one place and are now wondering whether your goals still align with the school’s direction, that tension is worth paying attention to.
When you start a new job, it is natural to be energized by a shared mission. You may have joined because the school’s vision was exciting, the leadership was promising, or you believed strongly in the work being done. However, schools evolve over time. Leadership changes, priorities shift, and even the best-fitting role can begin to feel mismatched. That does not necessarily mean anything is wrong with you — or even with the school. It may simply mean that the fit has changed.
Listen to the Quiet Signals
Most people do not wake up one day and suddenly realize it is time to leave. More often, the decision builds slowly. You may notice that you feel drained more often than energized. You may stop feeling connected to the mission. You may find yourself saying yes out of loyalty, but feeling increasingly disconnected from the work.
Another sign is when your professional growth stalls. This is what happened to me. I started getting bored, and when I asked for new opportunities, they didn’t come as readily as I needed. Schools should challenge us in healthy ways and help us continue learning. If you have gone from feeling inspired to feeling stuck, that is worth reflecting on. Ask yourself whether the school still offers the kind of environment where you can grow, contribute meaningfully, and feel respected. If your answer is no, maybe it is time to start looking elsewhere.
Ask the Right Questions
Before making any big decision, it helps to ask yourself a few honest questions:
- Do I still believe in the school’s direction?
- Am I staying because I am committed, or because I am comfortable? (This one was a big one for me at the school I was at the longest — it was so hard to leave, even though it was the right time.)
- Have my values changed, or has the school’s culture shifted?
- Do I feel seen, supported, and professionally valued? (This was another big signal for me – my principal actually told me everyone was replaceable.)
- If nothing changed for the next two years, would I still want to be here?
These questions can help you separate temporary frustration from a deeper misalignment. Every school year has difficult seasons. A challenging group of students, a leadership transition, or a stressful initiative can make any job feel heavy for a time. But if the discomfort is persistent and connected to your sense of purpose, it may be telling you something important.
Loyalty Should Not Replace Alignment
Many educators stay longer than they should out of loyalty. They love their colleagues, care about their students, and do not want to disappoint anyone. That loyalty is admirable. But staying in a school community out of obligation alone can slowly wear you down. This was very much the case at the school I was at the longest. I felt responsible for my students and their families, and my colleagues, too. Plus, my leaders gave me so many opportunities, until they didn’t.
It is possible to appreciate what a school has given you and still recognize that your season there may be ending. Leaving does not mean you failed. It means you are being honest about what you need in your professional life. If the school community really cares about you, they will want you to grow and be happy.
Leave Thoughtfully, Not Impulsively
If you are considering leaving, you do not have to make an immediate decision. Start by gathering information. Reflect on what you want more of in your next role—more autonomy, more collaboration, stronger leadership, a different grade level, or a new kind of work altogether. Talk with trusted colleagues or mentors. Update your resume. Explore what else is available. Sometimes clarity comes not from forcing a decision, but from allowing yourself to look ahead with curiosity. I always suggest that folks create the job description they want to help gain clarity. I talk about this in my book, Making an Impact Outside the Classroom. It includes activities you can do to get clear on what you want, and some different pathways that are available as an educator.
The Right Time May Be Sooner Than You Think
The right time to leave is not when you are completely burned out. Ideally, it is when you can make the decision with perspective, professionalism, and hope for what comes next. If your values no longer align with the school’s direction, and you have given yourself time to reflect on that honestly, then it may be time to begin your next chapter.
A school community can be meaningful to you and still not be the place where you are meant to stay forever. Sometimes, the most professional, courageous thing you can do is recognize when your growth is leading you in a new direction.
If you have an issue that you would like me to address, please email me at ssackstein@educatorsrising.org or complete this form. You will be kept anonymous.
ABOUT THE AUTHOR
Starr Sackstein
Starr Sackstein is the Massachusetts state coordinator for PDK’s Educators Rising program, COO of Mastery Portfolio, an education consultant, instructional coach, and author. She was a high school English and journalism teacher and school district curriculum leader. She is the author of more than 15 educational books, including Hacking Assessment (Times 10, 2015), Making an Impact Outside of the Classroom (Routledge, 2024), and Actionable Assessment (Routledge, 2026).
Visit their website at: https://www.mssackstein.com/
