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The Classroom Exit Strategies Podcast
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The Classroom Exit Strategies Podcast

Author: Jennifer Holt

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A podcast for teachers who are thinking about leaving the classroom to pursue a different career path or are simply curious about starting a teacher side hustle. Discover what you need to have in place BEFORE you resign from your teaching job including how to best replace your teaching salary outside of the classroom, the best jobs for teachers who don't want to teach, what you need to know about your teacher retirement, and how to find appropriate health insurance. We'll also dive into topics like how your mindset is holding you back, how to get more done in the small amount of time you have outside of the classroom, whether you need to create a teacher LLC, and how to cultivate a self-sustaining business that you love OUTSIDE of the classroom! Find amazing guest interviews with some of the biggest names in education who have left the classroom and have thriving businesses, teachers who are still in the classroom and have booming teacher side businesses, as well as experts in the fields of law, business, and accounting so that you are prepared to take the next step successfully. 

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With increasing learning deficits observed in students since 2020 and increasing demand for personalized education, teachers have become a vital resource for students seeking extra academic support. In fact, tutoring has become a relevant source of income for many teachers. But that begs the question, How much do teachers charge for tutoring?Well that's a great question, but to figure out what your private tutor rates would be, we need to pull back the curtain on what other factors need to be considered.  While we know tutoring is an excellent way for students to gain more in-depth knowledge of a subject, strengthen their academic skills, and improve their academic performance, it is also a lucrative option for teachers who want to supplement their income or take the first step in their exit strategy from the classroom. 📝  Click here for a transcript of this episode.Links mentioned in this episode:Website Design ServicesOne-on-One CoachingFollow me on IG @classroom_exit_strategies
If you have a TpT shop or have considered starting one, you’ve probably heard talk about some of the issues that have arisen on the TpT platform regarding search issues, security concerns, and the acquisition of TpT by the IXL platform.And each of those can be super-terrifying, which is why many teachers are running scared.  They are fearful…their income is going to tank, andall of their work will be for nothingTherefore, many have decided to add an e-commerce shop to their own websites in order to sell their resources.  And if you've been listening to any of these conversations, one e-commerce solution is garnering a lot of attention in the teacher entrepreneur space…and that is WooCommerce.I personally have a WooCommerce shop, but that is getting ready to change.Why, you might ask?Well, I reached out to my "go to" tech guy, Grayson Bell founder and CEO of iMark Interactive, with a couple of questions about setting up a WooCommerce shop for a client...And he dropped a bomb on me when he said, "To be honest, Woo is such a terrible e-com system. I wouldn't recommend it for anyone anymore."To say I was shocked would be a gross understatement. After recovering from that startling revelation, I knew I had to ask if he would be willing to come on the podcast and share his insight, reasoning, and suggestions for teacher entrepreneurs.And trust me when I tell you that if the tech side of starting a blog or website scares you, then this is the guy you want in your corner.So he is here today to share all of his insight regarding Woo Commerce and which e-commerce solution is going to be the best for teacher entrepreneurs.📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
Making a career change can be a scary prospect! The reality is most of us choose a career path and plan to stay the course until we retire. But if you’re feeling more and more convinced that you need to pursue other options, then this podcast is for you.Today we are going to explore the best career changes for teachers who want out of the traditional classroom and are actively seeking other alternatives.Now I know we’ve spent time touching on the topic of seeking a new career path before, but today we’re going to look at...15 of the best jobs for teachers that capitalize on your transferable skills and your experience in the education field,why they are each considered the best career change for teachers,and how to determine which one you should pursue.So if you’re ready, let’s do it!📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
There are as many different types of teachers in the world as there are grains of sand on the beach. We are all unique individuals with specialized skill sets, which is why we are the most enticing candidates for any position.But have you ever considered the idea that the type of teacher you are might actually be providing you with clues as to what job you should pursue outside of the classroom?Interesting thought, amiright?While we’ve established that we’re all great teachers, there are certain characteristics and traits that tend to surface within different groups of teachers that make them ideally suited for certain careers.So we’re going to take this wealth of information and filter it three different ways in order to help you narrow down your prospective options including…Age group taught,Content knowledge and subject area, andTeaching stylesIf you’re ready to dive in, let’s do it!📝  Click here for a transcript of this episode.Links mentioned in the episode:Fresh April FloursBunsen Burner BakeryFollow me on IG @classroom_exit_strategies
The best way to be able to leave the classroom is to be more efficient while in the classroom. This will allow you to spend more time focused on your exit strategy and/or your side hustle.In order to do that, we need to determine how you can accomplish everything you need to in less time so you are able to leave as soon as your contracted hours are complete.And of course, this means we need to narrow down the absolute best time management tips for teachers because good time management skills don’t just happen by accident.But you're in luck because that is exactly what today’s blog post is all about. We are going to discuss how to…determine your most important tasks (even when everything feels equally important),set boundaries so your professional life doesn’t bleed over into your personal life, andsuccessfully and consistently apply these tips in order to leave the classroom📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
Whether you want to be hired for your first teaching job or simply find a different teaching position outside of your current school, in a different district, or another grade level, it's essential that you understand the common weaknesses of teachers. I know this sounds ridiculous, but as you seek employment even as an experienced teacher, you be required to be interviewed. And with that interview you will be forced to answer the two trickiest questions in the world...What is your greatest strength? and What is your biggest weakness?The truth is...your answers to these two questions could be the deal-makers or the deal-breakers. And while many articles you read (or podcasts you listen to) focus on how to answer the strength part of the question, I want to dig into the weakness question because I want to help you...honestly answer these questions without sounding totally arrogant or completely spineless,strengthen some of these weak areas (before you interview), know how to prepare exactly what you will say ahead of time (with sample answers), andincrease your confidence before you step foot into the interview.📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
We spend a lot of time discussing how to make money outside of the classroom, how to start a website, how to find jobs in other fields, how to set goals for yourself, and the list goes on.But today I want to talk about something I've never talked about before...teacher leave.  Understanding what types of leave you can take (and when you can take those times of leave) could actually be the first step in your exit process.However, for that to be the case, we need to dig into questions like...How long do teachers get for maternity leave?How does FMLA work for teachers?Can I use FMLA even if I plan to leave the classroom permanently?How much of a role do school districts play in personal leave, sick leave, and /or annual leave?What does this information have to do with my exit strategy?And what about the teacher with a chronic illness?  What about the teacher who is ready to leave the classroom, can that teacher use leave?Well, that's exactly what we're going to explore in this episode!!📝  Click here for a transcript of this episode.Articles and Info Mentioned in this Episode: Comparison of Different Types of Leave PDFFrequently Asked Questions About FMLAAnalysis of Sabbatical Leave Clause (NJ Teachers)Follow me on IG @classroom_exit_strategies
Let's face it, we all have things we want to accomplish in our lives. But it seems like we get so distracted from the big things because of all the little fires we have to put out each day. We have great intentions, but rarely do those intentions actually come to fruition because we're so busy just doing the day to day stuff. Then we look back a few years down the road wondering why we never accomplished that 5 year plan we had for ourselves.We know what goals are, and we may have even participated in a few goal setting sessions during our life. But for whatever reason, we just didn't make those goals a priority in our lives and now we're once again at a crossroads trying to determine whether to give up on our dreams and just continue aimlessly walking through our lives or finally work toward achieving those big dreams.So today, we're going to finally take the first step toward creating meaningful goals and look at individual goals examples you need to address in your own life. And just to be clear, yes, it's going to mean...setting aside time to think through the good things you want for your life,facing some of our bad habits head on,acknowledging that we are aren't necessarily where we thought we would be at this point,realizing that we can change our path, andputting in the hard work needed.This isn't going to just be a quick thing you do in between phone calls so you can check it off your to do list. This is going to require you to get out of your comfort zone, put forth a concerted effort in order to dig into some uncomfortable things, and learn some new skills. But aren't your biggest dreams worth mucking through some discomfort?If you said yes, then let's do it!📝  Click here for a transcript of this episode.Articles Mentioned in this Episode: 11 Effects of Sleep Deprivation on Your Body10 Surprising Effects of Lack of SleepExtent and Health Consequences of Chronic Sleep Loss and Sleep DisordersJust One Night of Sleep Loss Harms Your Well-Being, New Study FindsFollow me on IG @classroom_exit_strategies
As classroom teachers, we're constantly learning and setting goals for ourselves. Unfortunately, just setting a few superficial goals isn't enough to take us from where we currently are to the level of effective teachers we might want to be.Goal setting requires you to dig deep into what you hope to accomplish, why you want to achieve it, and how you plan to make it happen.Maybe you're a brand new teacher just beginning your teaching career and you want to set yourself up for success or maybe you're one of the many experienced teachers with a lot of years in the classroom and you want to make an even bigger impact on the kids in your class.Either way it's essential to reflect on the direction you're headed because the truth is, the amount of time you've been in the classroom is irrelevant to the career goals you set for yourself.But that brings us to a series of interesting questions as we think about setting professional goals for teachers... What if you don't intend to continue teaching until you retire?Do you still need to create professional goals for yourself? What if you are on the fence about leaving the classroom?Here's the truth; teaching is hard. Discussions about how difficult teaching has become flood social media daily, and teachers everywhere are questioning whether or not they want to continue down this path.But whether you intend to leave the classroom at the end of this school year, five years from now, or never, you need to take a step back and determine new ways to connect with the students who are currently in your classroom.So, we're going to look at a professional growth plan that will help you make strides in setting and crushing your professional goals inside the classroom, apply this same approach to your personal goals outside of the classroom, and how to move forward from this point.📝  Click here for a transcript of this episode.Product Links Mentioned in this Episode:  (affiliate)Cube timerThe Five Love LanguagesFind Your PeopleHow to Win Friends and Influence PeopleFollow me on IG @classroom_exit_strategies
Goals and objectives are words we hear frequently as teachers.   But do you actually know the difference between the two?Without blinking an eye, most of us would yes.  However, if we were asked to explain the specific distinguishing factors, we might be a bit stumped.Now, you might be thinking, "Does it really matter?"  And the answer is yes!!So in this podcast episode, I want to...define goals and objectives, discuss the 5 major differences between the two, determine how you can create a clear action plan that will set you up for success, discern whether or not you're progressing at the appropriate pace (and in the right direction),describe how all of this relates to leaving teaching, opening a TpT shop, and becoming an entrepreneur.📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
If you're a teacher, you know that the income generated from a teaching salary is typically far below that of other professionals with college degrees.  Because of this income discrepancy, many of us want to know how to make money in education. Well, going back to school and getting a Master’s degree, or another advanced degree is one option, but the increase in your salary is usually minimal for the amount of time required, and truthfully, it's only helpful if you know you plan to stay in the classroom.You could spend your summers teaching summer school, but then you severely limit your "recharge" time and the pay isn't always as good as it could be.But another option is starting a side hustle or getting a second job in order to help increase your yearly income. This would obviously require a time investment, but what if you were able to find something that... allowed you to stay in the education field, was super-flexible and wouldn’t interfere with your brick and mortar teaching job, was able to be done remotely from home, and was interesting enough to force you outside your comfort zone and potentially into a different career altogetherWould you want to learn a bit more?Well, I'm 100% confident that you said yes, so I’ve put together a list of some of the greatest work from home jobs for teachers.  They are ideal for weekends, school breaks, summer months, and as though that wasn't enough, they are also uniquely suited for teachers who are thinking about leaving the classroom to become an entrepreneur or pursue other careers outside the classroom.  And they are things you can start doing now in order to save up the money you need to leave and get you the experience you need to take them full-time.  Yep, you heard that right...every single one of these options has the potential to become your full-time job. 📝  Click here for a transcript of this episode.--> Selling on Teachers Pay TeachersInterviews mentioned in this episode:Joey Udovich Michelle Griffo from Apples and ABCsTanya G. Marshall from The Butterfly TeacherNicki Dingraudo from The Sprinkle-Topped TeacherFollow me on IG @classroom_exit_strategies
Teacher shortages are showing up in school districts everywhere with many school systems finding themselves in the unenviable position of having to hire individuals without teaching degrees just to fill vacancies.But what has caused this record number of teachers to leave?  Was the great resignation of the 2021-2022 school year just a fluke?  And are teachers going to continue leaving in the middle of the school year?Well, if you want to understand why so many teachers are thinking of quitting (and actually following through with it) we need to face some hard truths.But before we dig into those, I want to share some good news.If you’re an administrator, policy maker, or state leader, who genuinely wants to see qualified and effective teachers filling up schools again, there is hope!It is possible, but it starts with listening carefully to what teachers are saying, understanding what is happening, and being willing to work together to create solutions.And if you’re a teacher, you need to pinpoint exactly what’s causing you to question your career choice, so that you can be a conduit of change and fall back in love with teaching. In this episode, we are going to look at the most common reasons teachers are leaving in droves and what can be done at every level to change the outcome.📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
By now, every teacher on the planet is familiar with the Teachers Pay Teachers online marketplace. With millions of great free resources from amazing TpT sellers, there are just so many original educational resources for teachers to use in their own classrooms. But you might be thinking, "Ok, but what about teachers who want to earn an income by selling TpT products?"Well, I am so glad you asked because this entire episode is all about how to make money on Teachers Pay Teachers...even in 2022!!And don't think this is just for those who want to start selling on TpT.  I also have several suggestions for veteran sellers on how to increase your sales.  So we're going to spend time talking about...Where to begin,What type of membership is best for you,How much time you need to devote to your TpT store to make it work,What teacher resources you should sell,How to market your shop,Ways to increase your sales and trafficOne thing I want to make clear from the beginning.Yes, making extra money on TpT is absolutely possible, but many new sellers drop out when they have to put in the hard work of creating resources and don't see an instant turnaround on their investment of time.I will be honest and tell you that opening Teachers Pay Teachers shop is more involved that just creating a cute product.But don't let the fear of hard work deter you from your goal because opening up a shop can be an excellent side hustle that provides passive income until it eventually turns into your full-time job.So if you are willing to apply what I share, I can walk you through how to make money on Teachers Pay Teachers. 📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
It’s no secret that over the last several months and years teachers have been leaving teaching in droves.  But what exactly are these teachers doing now that they are no longer in the classroom?  Well, some have left to pursue careers in different fields, but many have embarked on an entirely new journey as entrepreneurs.  Now you might think that’s great for them but you don’t see that as an option for you.  Maybe you’ve just resigned yourself to the fact that you’re going to be stuck in the classroom for the rest of your life because you’re just not cut out to be an entrepreneur.Well, I hope this episode changes your mind because whether you feel like you were born with an entrepreneurial spirit or not, I’m going to tell you why teachers make the best entrepreneurs.  And yes, that even includes you!📝  Click here for a transcript of this episode.Links Mentioned in this Episode: Free Coaching Meeting with JenniferFollow me on IG @classroom_exit_strategies
Today we're going to be jumping down into the rabbit hole of WordPress with the ten best free WordPress plugins for a teacher blog.  However, don’t let the title of this particular episode scare you or potentially cause you to quit listening because it is going to be immensely helpful...even if you are just in the consideration stage of creating a website or blog.As I’ve said many times, this world is becoming increasingly technology-based, and that means just about every business has at least a few components of the business based online. Whether it's specific programs, products, content, or a website, learning about WordPress websites will increase your depth of knowledge about the online space and it may also give you the confidence boost you need to realize this is something you CAN do!📝  Click here for a transcript of this episode.Links Mentioned in this Episode: Jennifer Holt Designs - Custom WebsitesFollow me on IG @classroom_exit_strategies
Before I share why quitting teaching was the best thing I ever did as well as the ten things I’ve learned after quitting teaching twice, I want to share my heart.This podcast episode is not intended to knock teaching or anyone who chooses to continue teaching.  I absolutely loved teaching; in fact, (spoiler alert) I am working with kids this school year. Working with children, guiding them to success, and helping them grow their self-confidence is what I used to believe I was created to do.  Now you might be thinking, “Wait a second…if that’s what God designed you to do, shouldn’t you be doing that?”  Well, that is a very astute point.  And here’s what I’ve learned.While I was comfortable teaching early childhood and elementary-aged children and staying in my comfort zone, it became clear that the path I had mapped out for myself was NOT the best path for my life.Sometimes I think the Lord has a sense of humor because those things that I always said I wouldn't do are those exact things He seems to have waiting in the wings for me.But looking back now, I am soooooo grateful for the swift kick in the pants I needed to make  tough decisions like quitting teaching because it’s a whole lot easier to stay stuck than to muster up the courage to venture out onto an unknown path.But if I can do it, you can too and that is what today’s episode is all about. 📝  Click here for a transcript of this episode.Links Mentioned in this Episode: Jennifer Holt Designs - Custom WebsitesJob opportunities for teachersFollow me on IG @classroom_exit_strategies
Once you decide it's time to leave the classroom, your obvious next step is creating an amazing resume. But did you know that there are some resume myths you need to avoid in order to get the interview (and position) to which you are applying?You may think this sounds crazy, but it has probably been a few years (or maybe even MANY years) since you've designed a resume. And I want to spare you the agony of unnecessary rejection letters by sharing 5 resume myths that you may not realize are faux pas in the realm of resume creation. 📝  Click here for a transcript of this episode.Links mentioned in this episode:Research on professional email addressesResearch on typos in your resumeWant help updating your resume?  Click here to find out how I can help!!  :)Follow me on IG @classroom_exit_strategies
If you're interested in starting a blog, you will find so much information on the Internet.  Everyone claims to be an expert in helping others find success blogging.  However, you should be mindful of who you listen to because you want their results to be your desired outcome.If you know blogging is something you would like to pursue, starting a website is going to be a vital piece of the puzzle.  But where should you begin?  Well, the first thing you want to do is listen to episode #37 and make sure you are familiar with the basics of starting a website.  Whether you hire someone to create your website for you or you choose to DIY your way to an amazing website, there are some essential components you need to include, and that's what today's episode is all about.So let's dive head first into the 6 core essentials necessary for your website to be a successful platform.   📝  Click here for a transcript of this episode.Links mentioned in this episode:Jennifer Holt DesignsThe 6 Essential Components GuideFollow me on IG @classroom_exit_strategies
I’m going to be completely honest...knowing how to start a successful website with no prior knowledge of the “techy” lingo is tough.  I found that out the hard way when I decided to start my blog back in 2016.  I literally just woke up one day with this hair-brained idea that I would start a blog.  I figured it wouldn’t be that hard; I would just write some pretty words, maybe mention some interesting stuff, and people would love it.   Ahhhh, gotta love 2016 Jennifer…she was just so clueless.What I discovered was a seemingly insurmountable learning curve that I almost quit on at least 50 times.  Every single task was new.  The language was new, the platforms were new, and I knew absolutely zero about any of it.I spent hours every day trying to figure out what I was doing, and those hours turned into days, weeks, and eventually months of learning.Now, you might be wondering why after all that struggle I would suggest that anyone else dive into the deep end.  Well, I am so glad you asked because even though you are jumping into the deep end, I am going to teach you everything you need to know to stay afloat!Today we are going to talk about the 10 things you need to know to start a successful website from scratch.  There is a lot to it, but I promise, it’s totally doable once you know the language and understand the central focus.📝  Click here for a transcript of this episode.Affiliate Links Mentioned in this Episode: MailerLite - Email Service ProviderSiteGround - Website HostingJennifer Holt Designs - Custom WebsitesRestored316 - Website ThemesFollow me on IG @classroom_exit_strategies
Starting a TPT shop is an amazing endeavor!  But for it to be sustainable, you to know how to grow your TPT business. The truth is, it can be an exercise in futility if you find yourself constantly stuck answering the same questions through email and the feedback section of your TPT store.  So what’s a TPT seller to do?Well, why not increase your TPT sales and grow your TPT business with a teacher blog?  Now before you run away screaming, “Awesome, another thing to add to my overflowing plate,” let me explain and quantify exactly what I mean by a blog in this particular context.  I’m not talking about a day in your life, a lifestyle blog, or anything outside of what you create and sell within your TPT shop.  You need to grow your TPT business with a teacher blog that is focused on content related to your products and helps solve the problems of your readers because this will ultimately lead to more eyes on your products and more sales. Unfortunately, this is where many blogs break down.  Bloggers who are uncertain about who they serve or unclear on the problems of their readers and customers will struggle to create content that lots of people want to read.So in today's episode, I'm sharing some of those painstakingly slow realizations in the form of the 5 most underrated benefits creating a blog will do for you..and ultimately your TPT shop.📝  Click here for a transcript of this episode.Follow me on IG @classroom_exit_strategies
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