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40 Hour Workweek

Mindset & Motivation, Edupreneur Resources, Podcast Articles   |   May 5, 2019

How do you know when it’s time to quit teaching?

By Angela Watson

Founder and Writer

How do you know when it’s time to quit teaching?

By Angela Watson

I read a comment on a thread in the 40 Hour Teacher Workweek Club that I just can’t stop thinking about.

It’s from a teacher named Rosie. She wrote,

“My wife and I are planning on beginning the adoption process in the next year or so. I’ve implemented many of the strategies from this group for over a year, which has helped tremendously with being efficient and developing systems to decrease the number of hours I am working (at one point I was working 70 hours a week). However, I now know that in order to be the parent I want to be AND be satisfied with my professional life, I would need to make significant changes beyond the scope of this club.

After 11 years in the classroom, I have decided to leave the classroom once this school year is over. I’ll be pursuing a private practice in Educational Therapy. This will allow me to have the flexibility I will need to get to know (and raise) my child. This club helped me to implement many tools to improve my work/life balance and to really focus on priorities. It is bittersweet, but I feel confident and excited to be focusing on my priorities.”

I think the reason why that comment struck me in such a powerful way is that it illuminates something I don’t think I’ve said often enough on this podcast, or anywhere for that matter, and it’s this:

Teaching does not have to be a lifelong career. You are not a failure if you decide you want to use your gifts and talents in another way.

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I remember people asking me when I was little what I wanted to be when I grew up. And I always knew, I wanted to be a teacher. Now I’m about to turn 41, so I grew up during an era when folks tended to choose a profession when they were young, get the training or schooling needed for it, and then stick to that profession until retirement.

This was the path that the generation before me took: it wasn’t unusual for my parents’ friends to stick with the same company or organization for decades. They’d get a gold watch at retirement to thank them for their service. The generation who raised me thought that way and trained me to think in that way.

I assumed I’d get a job as a teacher and stay with the same district until retirement so I could collect a pension. I remember interviewing for my first job and the principal asking me about my career ambitions, and I was totally stumped. It seemed like the strangest question to ask: I’m here interviewing to teach kindergarten. I want to be a teacher. Why else would I be here? What else is there? And I basically told him that: I want to be in the classroom forever–it’s all I’ve ever wanted to do.

For some people, that will hold true. But for me, it didn’t. And because I had always thought of myself as a teacher and pictured myself teaching in the same place for decades, it created a bit of an identity crisis when I realized that wasn’t making me happy anymore.

I was getting restless and wanted new challenges. I changed grade levels, then relocated from Washington DC to Miami, then changed grade levels again and went to Fort Lauderdale.

I’ve done a whole podcast episode about my decisions to quit, so I won’t delve into that here. But I will tell you I was wracked with guilt when I decided after 11 years to leave the classroom. Part of me felt like a failure, like I couldn’t hack it as a teacher for any longer.

It made no sense, particularly since I was going to be doing instructional coaching, which was my dream job at the time. Moving away from classroom-based work has freed me up to make an impact in education in ways that would have been impossible if I was responsible for a classroom full of students. This podcast, my books, and so on would have continued to be a part-time hobby (if they’d even happened at all.) So it’s not like the next phase of my career wasn’t purposeful.

I just felt like teaching was something a person did for life. I suppose this fits in with the “teaching as a calling” narrative: you don’t quit a calling. Being a teacher was like a calling for me–it was part of my life’s purpose. What was wrong with me? Had I lost my way?

Not only did it feel like a personal failure to quit, but it also seemed like a disrespect to the profession. In my mind, teaching was not something you just dip in and out of: “Oh, I’ll teach for a few years and then do something else.” Either you’re a born educator who is committed to our students or you’re not.

So it was a shock when that belief no longer held true for me personally, and I don’t think I’m alone in that, particularly as the profession becomes more demanding. Many people feel like Rosie, the teacher I introduced you to at the start of the episode.  In order to be present in her family life the way she wanted to be, she needed a job that had more flexibility and less stress. The job she signed up for just wasn’t aligning with the rest of her life circumstances.

And this was something I don’t think those of us who started teaching years ago really could have predicted. Teaching was never an easy job, but the amount of paperwork, documentation, meetings, and overall pressure on educators has undoubtedly increased. Everything from the evaluation system to testing, demands from parents to the increased challenges students bring to our classrooms … it’s a lot more than some of us thought we were signing up for years ago.

I think there comes a time for a lot of educators to re-evaluate:

  • Is this what I want to continue doing until retirement?
  • Do I have another 10, 20, 30 years in me, and if not, at what point do I begin the transition into something else?
  • Is the quality of life I want possible in this field, or within this particular classroom-based assignment?
  • What are the trade-offs I’m making financially and in terms of time?
  • How could my life be different if I pursued another path?

I think these are really good questions to ask. And it’s something that I feel the millennial generation really gets: they are far less likely to enter a profession expecting to work in the same place for their entire lives. They may work in one field for a couple of years and discover that there’s a pivot they can make, and transfer those skills they’ve gained to something slightly or even completely different.

This is a healthy adaptive strategy that I think reflects how quickly the world is changing. There are professions now that didn’t exist when any of us were younger, and there will be new roles to play 5 or 10 years from now that none of us have yet envisioned. It’s crazy when you think about how many different ways people earn a living now, and the number of folks like myself who sort of make up our own jobs and create the position we want.

So, what if we thought of our careers as a portfolio of varied accomplishments, rather than one single thing we spent a lifetime building?

What if we aimed to look back on our lives and see a variety of ways we made an impact and made a living?

Wouldn’t that be healthier than telling ourselves we got a degree in education so we have to keep teaching forever even when it’s completely burning us out?

If you’re reading this post, my guess is that you’ve considered quitting teaching at some point, and I hope this perspective helps release you from any assumptions that just because you started off teaching, you now are obligated to keep teaching until your retirement. I think it’s perfectly respectable to choose to teach for a while and then choose something else.

People do this in other fields all the time: It’s assumed that they’re not going to keep doing the same type of work forever. It’s not a failure if an HR manager decides to move to the marketing team. And it’s not a failure if a teacher decides to become a speech therapist or interior decorator or real estate agent or anything else. The skills you develop as a teacher are so broadly useful in so many contexts that the time you spent teaching is almost certainly going to be valuable in another profession.

So as much as I’d love to tell amazing teachers, “Please stay — we need you in our classrooms,” I think that’s a message you’re going to hear basically everywhere else. I’d like to offer you a counterpoint, which is that we need you in the world, in general, and teaching is just one of an infinite number of ways you can contribute great things to the world. If it’s not THE way you make a difference for your entire lifetime, that’s absolutely fine.

Obviously, this has been my path and I’ve never regretted it. If you are itching to break free from the system and carve out a different path for yourself like I was, you can do that, too. I’ll never be the one to pressure you to stay because I remember how it felt when people did that to me.

They’d all say, “Oh you can’t quit, you’re sooo good at this! The school needs you! Your students love you! You can’t leave!”

But of course, I could quit. My replacement was hired within a week of me submitting my resignation. Other people wanted me to stay for their own reasons, but I was the only one who could really see a different vision for my life. I had to choose to act on it even when everyone said I was crazy to leave a secure job with a pension that I was really good at.

When it’s time to go, you’ll know it. That’s all I can really say about that. You’ll feel it deep in your bones. The idea of setting up your classroom in the fall and meeting a new group of students won’t bring that sense of anticipation and excitement, and will feel much more like a knot in your stomach.

You’ll know — it’s time for the next chapter in my life. Staying in your job will feel like a betrayal of yourself. Leaving will feel like a betrayal of your commitment to your students or your school, which is what makes it so hard — but staying will feel like a betrayal to you, and that’s something that is unbearable.

I realize that transitioning out of the classroom is not an easy thing to do. I’ll tell you something I haven’t ever shared publicly before: I’m in a bit of a transition myself. I know this episode is about you, but can I talk about me for a second here?

I would love to help more people beyond teachers. I feel my own sense of purpose shifting and expanding now. I hear teachers telling me that the things I’m writing would be useful to everyone, not just teachers. That’s something I’m thinking a lot about — who else I would want to serve, and how else I can make an impact.

Also, I have wanted, for years now, to create some sort of support or training to help teachers move into the next phase of their careers. I feel like I’ve created things to make teaching more enjoyable and also simpler and less stressful, but I don’t have anything to give the teachers like Rosie who say, “Thank you, your books and courses and podcast were helpful, but now it’s time for me to move on to something else.”

Once you leave the teaching world, you’re leaving my world. I have nothing for you, and that’s pretty ironic given that I, too, left the classroom. I feel like I should have something to help the teachers who want to do something else but they don’t know what that something else could be or how to get hired outside of a school system.

This isn’t a new product announcement, by the way. I’m not sure what I could even offer. I’m hopeful about partnering up with an organization or group who guides teachers through this process. I’m sure there have to be folks who are skilled in the technical aspects of this stuff, like resume writing and interviewing and career transitioning, and the piece I’d want to offer is the mindset: giving yourself permission to do something else, to chase another dream or use other skills, to have the confidence to step into a career that lets you prioritize your own well-being and financial security. It takes a lot of courage to leave a good teaching job and believe that there are other ways you can make an impact in the world, and that’s where I feel like I could offer more support.

So I’m just putting that out there to you all. I have no plan at this point. If you want support in this area, tell me in the comments here. Introduce me to folks doing this kind of work, tell me what kind of resources you wish I had created or support you wish you had available to you. 

Seth Godin once said, “Winners quit all the time, they just quit the right things at the right time.” So, if and when you reach the point when it’s time to move on, I want you to feel good about the years of your life you dedicated to teaching.

You are not giving up … you are opening yourself up to new opportunities. You can use your gifts and talents in many, many other ways and continue to make a positive impact in the world even when you are not in the classroom.


After careful consideration, I’ve decided to partner with Daphne Williams as an affiliate for her Teacher Career Coach courseDaphne is deeply passionate about helping teachers transition into their next career, and as I’ve watched her work over the past year and a half, I’ve been super impressed with her integrity and the quality of her resources.

I brought Daphne on my podcast to talk about how to transition out of teaching. Check out that episode as a follow-up to this one for tips on updating your resume, finding industries that like to hire former teachers, and more.

Daphne has her own podcast now and frequently interviews teachers who have found new career paths. She also writes excellent blog posts, such as The pros and cons of leaving teaching during the pandemic.

If you’re considering leaving teaching right now, I truly believe Daphne’s resources are the best available to support you, and I hope you’ll check them out!

One last resource: I recently compiled some more info about Daphne and other resources to help you make a decision about leaving teaching here: Is it real burnout or pandemic fatigure? How to decide if you should quit teaching in 2021.

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Angela Watson

Founder and Writer

Angela is a National Board Certified educator with 11 years of teaching experience and more than a decade of experience as an instructional coach. She started this website in 2003, and now serves as Editor-in-Chief of the Truth for Teachers...
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  1. Do you know yet of a group (or groups) who can help teachers transition to a new career? If so, I’d love some information about them and who they are!

  2. I cannot tell you how perfectly timed this is! Just last week I sent in my letter of resignation. And just like you, people told me I shouldn’t quit because I was so good at what I do. I know the Lord has something for me, but for the first time, I literally don’t have a plan. I’m just being obedient to what I believe He is telling me. I have taken several responsibilities in addition to teaching having to deal with leading, mentoring, and planning. I really enjoy that. I’d like to incorporate them into my future position.
    Thank you so much for sharing this. It feels good to know I’m not alone!

    Your teacher fan,
    Lindsay Kinsey

    1. I got so fed up with the “you can’t quit–you’re so good” guilt trip that I started saying, “I’m also really good at scrubbing toilets, but that doesn’t mean my lifelong calling is supposed to be professional house cleaning. I have lots of different skills and they can be used in lots of different careers.” It sounds like you’re feeling the same way–your next phase of life may involve capitalizing on your mentoring, planning, and leadership skills. I’m excited for you!

    2. Hi Lindsay K.,
      I am feeling the same tug, but am not sure about the direction God is guiding.
      I was wondering how you are doing and if you have seen God provide you direction this summer.
      Debbie Loudermilk

    3. I feel late responding to this message since it’s now over a year but HOW’S it going? How do you feel about your decision now since it’s been over a year since this message was posted.

      Thank you, Lindsay

  3. Definitely interested in working with someone to figure out a career change. Teaching was not my calling, but I was lucky that I found I enjoyed it, until recently. There’s a lot out of my control in my district, and the stress levels are at an all time high. Problem is, like you said, I have no idea what I’d want to do next. If you ever pursue this kind of coaching I would be ecstatic!

  4. Just when I was starting to have fear and anxiety about my decision, I heard my name and my story on your podcast. This is Rosie, the teacher mentioned. Your words were timely, as I begin to close out the school year and start my new journey.

    Angela, I have some ideas about resources for teachers wanting to transition based on my own experience. I created my own thorough process for this transition after gathering resources, reading, learning, reaching out to folks in different fields and accessing community resources. I’d be happy to share my process and the resources.

    1. I would love to hear how you transitioned to something new! I don’t even know where to look!

    2. Rosie! I would love you for you to tell me more. Please shoot me an email so we can connect!

    3. I am also very interested in some guidance. I have been looking up other career paths I could take. I have many other interests but I’m not so sure of what I should focus on. Other than teaching and retail during college I have no idea what another career path would feel like!

          1. It’s coming out March 1st! It’s with Daphne Williams from Teacher Career Coach. She has some free helpful resources here for podcast listeners, and a paid program as well: TeacherCareerCoach.com/TruthforTeachers.

    4. Yes, please! I’m interested and eager to learn how to transition out and on to a new path.

    5. Hi Rosie,
      I know this reply is over 2 years old and I am not Angela, but I find myself in the same place you and Angela were in– I want out of education but don’t know where to start. I’ve followed Teacher Career Coach but I am trying to search every avenue and pick every brain that I can. If you’re open to it I would love to hear about your process and the resources you used.
      I hope you’ve found joy and quality of life in your new profession.

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