Leaving Teaching Monica Sherwood Leaving Teaching Monica Sherwood

Thinking of Quitting Teaching? Here's What to Do Next

Recent research shows that low pay and lack of support from administrators are two of the biggest factors driving teachers out of the classroom, which I don’t think anyone is surprised to hear.

In my unfortunate experience, being a teacher in many schools today is not about teaching — it’s about acting. 

Acting like you have the perfect reaction to each and every behavioral issue you come across; acting like your administrator is an all-knowing genius: like you don’t have your own thoughts or opinions, like parents are always right, like students are never out of bounds.  

That’s without even mentioning the responsibilities that teachers need to pretend are totally within the realm of their job title. Dealing with disruptive students, piles of paperwork, pressure to meet standardized testing goals, documenting each and every student incident just in case — the demands on teachers just keep growing.

Recent research shows that low pay and lack of support from administrators are two of the biggest factors driving teachers out of the classroom, which I don’t think anyone is surprised to hear.

You’re also probably not surprised to hear these frequent responses: “People don’t go into teaching for the money.” “At least you get summers off.”

Right. I went into teaching because I wanted to make a difference. I did have the summers off.  Some districts do pay teachers decently. 

But something that the general public doesn’t seem to really register or fully understand unless they see it first hand is how demoralizing it can be.  

When you couple that with increasing class sizes, lack of resources, and constant curriculum changes, it's a recipe for burnout.

Teachers are expected to be counselors, parents, and disciplinarians on top of actually teaching. But when they speak up about issues, their voices often fall on deaf ears. No wonder they feel under appreciated and overwhelmed. Until we start truly valuing educators and giving them the support they need, the teacher shortage crisis will only get worse.


P.S. I created my FREE downloadable guide Your Strategic Career Transition Toolkit just for you. It includes:

  • Your Skill Translation Cheat Sheet

  • Networking Quick-Start Guide

  • Industry and Career Ideas for Teachers

  • Methods for transforming classroom skills into corporate language for resumes and interview


Taking the First Step: Deciding if Quitting Teaching is the Right Choice for You

We all know the pros and cons: the ridiculous pressure teachers are placed under, the generally discouraging atmosphere surrounding so many schools today. When it comes down to it though, you need to decide what’s right for you.  

As someone who did leave, I can’t recommend it enough. But it was also very difficult, and it was pre-covid, so it was in a different job market. And even though it did work out, I wouldn’t want to go through it all again.

This is definitely not meant to discourage you — it’s to be realistic.

If there’s any part of you that can see yourself staying in teaching and not being miserable, I would probably recommend exploring that further before changing course. Are you interested in trying a different school setting? A different grade level? A different role? I say this because it’ll be easier than starting from scratch, and you may actually find your passion for teaching reignited after changing things up. I recommend checking out this post where I outline some tips on how to decide if you should quit teaching while you think things through.

But if you know that you are done with teaching, it’s time to take the next step.

I wrote a post here that outlines the steps unhappy teachers can take now to get clear on their goals. In this post, though, I want to talk about how to leave teaching.

Preparing for Your Transition Out of the Classroom

Whether you're burnt out, looking for a change, or just ready for something new, transitioning out of teaching can be a daunting prospect.

Start by doing a little soul-searching - what are your passions, your strengths, the things that get you fired up? Jot them down, because those are the clues to your next move.

To get you started brainstorming, take a look at this post I have on the 4 essential transferable skills for teachers and consider how they align with potential interests of yours.

Next, start networking and exploring your options.

You may have to start by looking for a bridge role — something that gets you out of teaching and positions you well for the industry you eventually want to develop a career in, even if it’s not where you start off.

This question is key:

Is it crucial for you to quit teaching, even if it means starting in a job that isn't your ideal choice?

If you're truly ready to say yes, you can begin taking steps towards a new career. You'll need to support and believe in yourself on this journey. You'll be in charge of where your career goes. Although it’s scary, it really is a great feeling to know that you’ve been your own biggest champion.

Exploring Alternative Careers for Former Teachers

If you're a former teacher looking to make a change, there are plenty of options that can put your skills to good use.

Many of the abilities you developed as an educator - like communication, organization, and patience - are highly valued in all sorts of industries. You could leverage your teaching experience into roles like training and development, HR, or even sales. You could put your expertise to work as an educational consultant, a curriculum designer, or even a freelance writer.

The transition from teaching to a non-teaching job might seem daunting, but with the right mindset and a little creativity, you can find a fulfilling new career path that aligns with your interests and skills.

I’m working on an in-depth guide on alternative careers for teachers with first-hand accounts and advice from former teachers who’ve successfully transitioned to other professions. You can sign up for my email list here to be notified when it’s posted.

It’s natural to be afraid when you start exploring a career outside classroom - but remember your teaching days have prepared you for all kinds of opportunities!

Maintaining Your Sanity and Finding Purpose During the Transition

It's totally normal to feel a little lost or unsure at first. The important thing is to be patient with yourself and focus on taking care of your mental health.

Sure, it might feel like you're stepping into the unknown, but that can also be exciting. Take some time to reflect on what really brings you joy and purpose. Maybe there's a new career path you've been curious about or a hobby you've been wanting to explore.

The key is to not put too much pressure on yourself. This transition is all about finding what works best for you. Lean on your support system, try new things, and most of all, be kind to yourself along the way. You've got this!

If you found this advice helpful and want more in-depth advice and support on transitioning out of teaching and so much more, subscribe to my substack newsletter here!


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Leaving Teaching Monica Sherwood Leaving Teaching Monica Sherwood

I Want to Leave Teaching: 5 Steps Unhappy Teachers Looking to Leave Teaching Can Take Now

Discover the 5 essential steps unhappy teachers can take now to prepare for a new career at the end of the school year. Stop dreading Mondays and start pursuing your passion.

 

I Want to Leave Teaching: 5 Steps Unhappy Teachers Looking to Leave Teaching Can Take Now


The other night I received a message out of the blue from a teacher who’d just wrapped her first week back in the classroom.

I should have figured something else out over the summer, but I was avoiding it, and now I’m miserable with a whole school year ahead of me. I feel trapped, and all I know is I want to leave teaching - now! What can I do?”

I think it’s easy to beat ourselves up when we’ve avoided taking action toward our goals. It’s harder to acknowledge that we’ve put off making a big decision because we know that making a directional change, especially about something as important as our career, is risky.

I felt this unhappy teacher’s pain. While the start of a new school year can be exciting and filled with potential, it can also be intimidating. And if it’s becoming clearer to you that your heart isn’t in teaching anymore, a new school year can be even more daunting. It’s easy to become overwhelmed and pessimistic.

I’d argue that this desperate, trapped teacher is actually at an advantage right now. She’s realized that she’s ready to make moves and leave the classroom with a whole school year ahead of her to plan and execute the switch.

If you’re in the same boat — a teacher wondering how to know when to quit teaching, or trying to get a handle on the transferrable skills teachers can bring into their next career — take a deep breath and relax. We’re going to talk about five steps you can put into motion right now so that when this school year ends, you’re able to successfully move on to your next opportunity confidently and at peace with your decision.

 

P.S. I created my FREE downloadable guide Your Strategic Career Transition Toolkit just for you. It includes:

  • Your Skill Translation Cheat Sheet

  • Networking Quick-Start Guide

  • Industry and Career Ideas for Teachers

  • Methods for transforming classroom skills into corporate language for resumes and interview

 

1. Reevaluate your goals

Take the time to reflect on your current situation and think about what you really want out of your career. Ask yourself why you're feeling unhappy and what you can do to make yourself happier. I wrote a while back about exercises I’ve used in the past to get clear on what I really want for myself and my life. I’ve actually returned to these exercises at different points in my own career and they do help provide clarity.

Take some time for self-reflection to identify the specific reasons for your unhappiness in teaching. Is it related to workload, classroom management, or other, personal factors? Maybe you’re sick of the administrative work, or you’re feeling endlessly exhausted. It could be a new curriculum being introduced, or a new admin who just doesn’t get what it’s like to be a teacher. Or, it could be that you’re ready to start making changes in your personal life but it seems impossible to find balance when teaching is taking every last ounce of your energy.

Think about why you became a teacher in the first place. Have there been positive moments that felt like you’d thought they would when you were training for your role in the classroom? Be honest with yourself. Try to think of the positive moments over your career and the impact you've had on students' lives. This might remind you of the difference you can make and might help reframe some of the struggles you’re facing now. Maybe teaching really is worth it to you, and you want to stay in the classroom – maybe it’s a different setting or environment you need.


Once you've pinpointed some of the identifiable pain points, it’s time to set some goals. These goals could be related to teaching specifically: adjusting classroom management strategies, trying to collaborate more with your grade team to balance planning, or finding someone at your school with a similar mindset to brainstorm how to approach admin specific challenges.

But this dedicated reflection time can also serve as a reality check.

2. Get clear on your values

Maybe you can’t remember why you decided to become a teacher at all. Or, maybe you didn’t have as much of a role as you would have liked in shaping your career, and it’s never been your passion. If that’s the case, then it may actually be an easier decision for you — you’ll have less attachment to the notions you had about teaching, and you can move right into brainstorming what’s next for you.

Or, you might realize that no matter how much you care about your students and their well being, and as much as you once felt you could make an impact in the classroom, you’re done. I think it’s really important to stress that this is not something to feel guilt or shame about.

It’s actually you getting clearer on what you value when it comes to work. I’ve actually taken values quizzes specifically about career goals, and it’s helped a great deal in helping to determine the facets of a position that have the biggest impact on my overall job satisfaction. For example, my highest value when it comes to work is freedom/independence. Knowing this, teaching was never going to work for me — for the majority of teachers, you are rarely free to make independent choices about how and you approach your teaching practice. if I’d identified these values earlier, maybe I wouldn’t have gone into teaching at all.

3. Define your boundaries

It's crucial to develop boundaries around your time and begin enforcing these boundaries NOW, as early into the new school year as possible. Why? Because you are going to need time this year you can dedicate to planning what’s next for you, and if you aren’t strict about your boundaries now, it won’t get any easier to start enforcing them.

Ask yourself: what amount of time are you willing to offer to your school community versus your own well being and your future planning?

I know this is especially difficult when it comes to teaching. The amount of pressure, side-eye, and judgment around how late you stay after school, your level of volunteerism for after school responsibilities, and your time spent prepping can be overwhelming.

If you find yourself second guessing your boundaries when it comes to coworker reactions, try to reframe your situation. Of course, you have to define what you’re comfortable with, but I’d recommend asking people outside of education their opinions about your time commitment to work. Let me tell you, their reaction to the amount of unpaid labor you provide might be enough of a reality check of how above and beyond you’re going for your school to help come up with some stronger boundaries.

And why are we so worried about implementing strong work boundaries? Because we are going to move onto Step 4.


4. Concrete career planning

After you’ve identified your career values and carved out regularly scheduled time dedicated to figuring out what’s next for you, you’re ready to get introspective. I have some specific exercises that can help you get specific about what you’re looking for in your next career here. What are your strengths? When do you find yourself in a flow state, where everything you’re accomplishing is happening almost automatically? Are there aspects of teaching that you do actually like? Write it all down and see if patterns begin emerging.

Based on your strengths and what you want your next career to look like, start researching. At first, cast a wide net. Look into the industries that seem most interesting to you. Look up companies or organizations that feel like they’d be a good fit, and find out a bit about their hiring process. Find out what you can about their current employees, a typical path to getting hired there, and identify what interests you about each of these companies.


Sometimes you can reach out for informational interviews via LinkedIn with a current employee that appears to be fairly junior. Asking for some advice based on your current situation respectfully can’t hurt. Important though, don’t get discouraged if someone doesn’t respond — not everyone on LinkedIn uses it regularly, or checks their inbox, etc, etc.

Be honest with yourself during this research process. What would a position in this new career demand of you? What skills would you’d need further training in to get hired? If you’d need additional training before getting a full time job, what would that look like? Consider each potential career shift with the big picture of your life in mind. Like with any life changing decision, there will be trade offs. You have to decide if you’re willing to take the risk and the action that this new career will require of you.

5. Develop a timeline

The reason that the beginning of the school year is a great time to begin taking action is because if gives you until next summer to get your ducks in a row. Is it realistic given everything you have on your plate at work and in your personal life for you to be ready to make this change by then?

If training is required in order for you to make the shift, is there a way you can do it virtually? For example, I completed Springboard’s UX Bootcamp while I was still teaching. It was definitely difficult, and might not be feasible for everyone, but it gave me a chance to develop the skills I needed for an entry level UX job while still getting a regular paycheck.

Can you come up with your own curriculum comprised of online learning resources? Depending on what you are looking to learn more about, there might be online courses offered from different universities virtually, or relevant Skillshare or Coursera courses.

Create goals and set realistic timelines for them. Check in with yourself as time progresses — are you on track to hit each milestone? If not, you have to shift how you’re spending your time or extend your timeline.

I can’t lie — it isn’t easy to face another school year when you’re not happy about teaching. But I’m here to tell you to have hope!

You can start moving toward a more fulfilling career now so that you have plans in place to make a change. Sometimes just being aware that you’re taking action and making progress toward a goal is enough to change your attitude and perspective. You have options — they just might not be clear enough to you yet. That’s why you’re starting now — so you have time to get clear and take actionable steps to build the career you want!


 

Hey, friend! Guess What?

I’m about to open up more spots for one-on-one coaching for teachers planning to leave the classroom!

Sign up for my waitlist below to be the first to be notified about availability!

 
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Leaving Teaching Monica Sherwood Leaving Teaching Monica Sherwood

4 Transferable Skills to Help Teachers Transition to a New Career

 

Breaking the Mold: How Teachers Can Turn Transferable Skills into Competitive Advantages

Thanks so much for reading the first two posts in my series, I Quit Teaching, Now What - I've loved hearing your feedback and your questions.  I plan to continue this series to dedicate time to helping you think further about how to best evaluate your teaching experience and skill set. 

If you've landed on the decision that you are ready to explore leaving the education space and taking on a new career path, congrats! Acknowledging this is the first brave step toward shaping the next phase of your life. 

Maybe, now that you've landed here, you feel unsure if you'll be able to utilize your skills in a different industry or role. If so, rest assured that as a teacher, you have so many transferable skills that you can apply to your next career. 

 

P.S. I created my FREE downloadable guide Your Strategic Career Transition Toolkit just for you. It includes:

  • Your Skill Translation Cheat Sheet

  • Networking Quick-Start Guide

  • Industry and Career Ideas for Teachers

  • Methods for transforming classroom skills into corporate language for resumes and interview

 


The summer I quit teaching, I spent at ton of time applying to jobs. Even though I'd decided I wanted to be a UX Designer, was in a UX training program, and was working on my first freelance projects, I applied to any and every job that seemed remotely open to me. Looking back I can see I just wanted some confirmation that I wasn't unemployable outside the education realm and hadn't ruined my life by quitting.

During interviews, I felt like an imposter speaking with any sort of authority about the soft skills I'd gained teaching and how I would use them to benefit a new employer.

Eventually, mostly out of desperation, I decided to employ the fake it till you make it approach to interviews; I had nothing to lose.

How? In order to boost my self belief and sell my claims, I developed tangible examples from the classroom that explained how I would be able to use my skill set in the role I was applying for. 

Developing these real life examples not only helped the interviewer to visualize how useful my skillset could be, but also empowered me to believe in myself and what I was saying as an interviewee. I realized that my background in education had afforded me with problem-solving skills that addressed a wide range of situations.  I had an almost endless supply of anecdotes that illustrated my social skills, organizational skills, and collaboration skills that I could apply to so many alternative careers. 

I'm sharing my own experience here as evidence of someone who successfully transitioned out of a teaching job and created a career in UX design.   There are so many relevant skills you can bring to any range of careers outside the education sector.  A big piece of marketing your transferable teaching skills successfully is determining what your career goals are for this next phase of your life. 

At this point in my UX career, I've had the pleasure of interviewing many former classroom teachers for design roles.  I see patterns in these candidates: strong public speaking skills, a high level of emotional intelligence, and effective communication skills.

I have a working theory that after you've run a classroom for a few years and handled all of the responsibility that goes with being a teacher, you can handle any career. 

When I've felt overwhelmed in my post-teaching career, I like to remind myself of the unique stress that comes with transporting 30 first graders on the subway through Times Square. Nothing I've faced as a designer, researcher, or writer has come close to that level of overwhelm and responsibility.

Reflect on that for a second.  In what other situation would you ever have to successfully monitor the well being of thirty or more children, employ strong time management skills to ensure a smooth field trip, utilize emotionally intelligent interpersonal skills to navigate talks with parent chaperones, navigate directions, manage your own stress levels, all while providing your students with a solid educational experience? 

No other career expects its professionals to juggle so many nuanced responsibilities all at once. 

With that in mind, let's get ready for some career exploration and skill reflection as I outline some of the top transferable skills teachers can bring with them to their future careers and how these valuable skills will empower you as you explore paths outside the classroom.

 

4 Essential Transferable Skills for Teachers, Explained and Reimagined

Transferable Teacher Skill #1: Communication

Communication skills are obviously crucial in every aspect of our lives, but are especially important in teaching. When you start to develop your own teaching style, you generally realize that your relationships with students have a real impact on student progress. This might also mean shifting your communication approach many times throughout the day as you interact with different students, colleagues, and parents.

The ability to communicate effectively with others is actually much more involved than it may seem at first, and when you're describing your soft skills, it's important to draw these nuances out.

Effective communication requires you to read others and adapt to their needs. This is a key skill that comes in handy in many roles, but is specifically useful in client-facing positions. Knowing how to approach a client or stakeholder, present work or deliverables to those stakeholders, and ensure that they feel heard when they provide feedback is not natural to many people. Chances are, it's something you've learned to do based on the number of people in different positions you interact with on a daily basis.

Few positions outside of teaching require such consistent face-to-face interaction with so many people in order to cultivate a successful career in a school community. Speak to this in interviews! Explain how this will benefit their team if they hire you, because believe me, it will! 

 

Transferable Teacher Skill #2: Leadership Qualities

Being a leader is inherent in teaching. You have to command attention in order to present lessons to students. You have 20-30 eyes focused on you most of the day. Let's face it, if you don't develop leadership qualities, your students will probably learn to walk all over you.

As a teacher, you use your leadership skills to motivate students, cultivate a positive classroom culture, and promote academic success. You delegate resources and manage classroom supplies to ensure your students can have enriching, hands-on experience in their classroom environment. 

Take a look at some job descriptions in job listings for positions in some of the alternative career paths you've been considering.  Some people work their entire careers to gain technical skills required to become a manager.  You've been prac

These are all outcomes that any workplace in any industry would strive for. Motivating colleagues, sharing your knowledge to benefit others, cultivating a positive team culture, and encouraging your coworkers to keep the end goal in mind are some tangible examples of how you can use these qualities to benefit your new role, whatever it might be.

 

Transferable Teacher Skill #3: Negotiation and Conflict Resolution

Knowing how to navigate conflicts and negotiate successfully can make you a valuable asset in any workplace. Of course, you've honed these skills under some of the trickiest conditions. Kids that are arguing, colleagues that can't see eye-to-eye, your own issues with administration. How do you communicate this specific set of skills in an interview? Being able to keep calm under pressure, focus on an ideal outcome, and reason with the unreasonable.

I'm sure it isn't hard for you to think of a few examples of conflict resolution if you reflect on the past day or two, but I would challenge you to come up with some examples that involve complicated politics or personality management. How have you negotiated what you think is best for your students and the requirements you are facing due to state standards or school mandated initiatives? When have you managed to be a voice of reason when your grade team wasn't seeing eye-to-eye on approaching a unit or breaking down work responsibilities? What have these moments taught you about how to interact with others moving forward, especially when you know that your ultimate goal is the same, though your approaches may be different?

 

Transferable Teacher Skill #4: Organization and Planning

Good organization and planning skills are transferable to virtually any career path, and you've probably been operating in a highly planned environment for as long as you've been teaching. Even if you don't feel like a particularly organized teacher (join the club!), chances are you rely on systems and routines to ensure student success on a daily basis. You've adhered to lesson plans while managing to accommodate a wide range of learning styles.

In interviews, you can outline how you've developed systems to align your classes toward achieving common goals.  You've leveraged classroom management to ensure high-quality student learning while also handling classroom dynamics, curriculum requirements, and effective time management.  These are huge accomplishments, and you should own them! 


 

Unlocking Career Opportunities: How Transferable Skills for Teachers Can Open Doors

As a teacher, it's easy to believe that our work experience isn’t applicable to careers in other fields. Don't sell yourself short or limit your potential at finding a more fulfilling career. Your experiences have equipped you with versatile skills that will help you thrive on any career path you choose. Embrace your strengths and focus on finding a job that excites you.

Remember, it’s all about how you frame and present your experiences! Highlight how what you’ve learned and accomplished as an educator has equipped you to be a valuable team player in your next position.

What questions do you have about transferable teacher skills? Drop them in the comments below!

And as always thanks for reading — it means so much!

 
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