PODCAST · business
Pretty Rich Teacher
by Dr. Jazmyne Dionne
Welcome to the Pretty Rich Teacher podcast (formerly known as the Exit Plan) where Jazmyne shares exclusive tips to help women in education turn their teaching experience into six figure careers and beyond with confidence.
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090: Putting Herself First: From Assistant Principal to Customer Success
If you're a teacher who feels like you've spent so much time taking care of everyone else that you've forgotten what you want, this episode is for you.In this episode, Jazmyne talks with Amber, a former assistant principal who left education for a fully remote Customer Success Manager role. Amber shares what led her to make the leap, how she navigated the transition while raising a family, and the mindset shifts that helped her stop putting herself last.When you listen to this episode, you'll walk away with:Insight into what the transition from education to corporate really looks like.Encouragement to embrace being a beginner and keep learning.The confidence to believe it's never too late to make a career change.Your teaching experience has value. Sometimes the hardest part is giving yourself permission to believe it belongs somewhere new.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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089: How Lauren Got Six Figures, Lost 15 Pounds, and Started a Business in 90 Days
If you're a teacher who has been watching from the sidelines, consuming every piece of content, trying to DIY your way out of the classroom, and still stuck in the first round of interviews going nowhere — this episode is going to show you exactly what happens when you finally stop waiting and go all in.This is a real conversation with a former middle school teacher who went from not knowing who she was outside of the classroom to landing a six figure sales role, losing 15 pounds, and mapping out her first business — all in less than 90 days.When you listen to this episode, you'll walk away with:Why DIYing your transition will get you interviews but not job offers — and what the missing piece actually isWhat it means to truly sell yourself in a corporate interview versus an education oneWhy teachers are overqualified for the roles they are afraid to apply forWhat to say to the people in your life who are going to speak fear into your decisionEvery day in that classroom is not just a bad day. It is a day you are not living your life.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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088: How to be Swimming in Interviews + Job Offers this Summer
If you're a teacher who keeps applying for jobs, getting silence back, and genuinely has no idea why, this episode is going to change that.In this episode, Jazmyne breaks down exactly what it takes to go from confused and stuck to landing interviews consistently, and what you need to stop doing immediately.When you listen to this episode, you'll walk away with:Why applying for any job and every job is the exact reason you are not getting interviewsWhat your resume is actually supposed to do — and why yours is probably not doing itHow to think about no's so they stop breaking your momentumThe exact number of jobs to apply to in 30 days if you want interviews this summerAre you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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087: Teacher to Corporate: The Story Behind My Six-Figure Career Pivot
If you're a teacher who has been quietly wondering if your years in the classroom could actually translate into a six figure corporate career, then this episode is your answer.In this episode, Jazmyne sits down with Adele, host of the Five for Two podcast, for a raw and honest conversation about what the transition from teaching to corporate actually looks like from the inside. From crying in her office with a student sitting across from her, to landing $85K in her first corporate role and crossing six figures in less than six months — this is the full story, unfiltered.When you listen to this episode, you'll walk away with:The moment Jazmyne knew teaching was no longer the plan — and what she did nextWhy teachers are walking into corporate roles and immediately outperforming everyone else in the roomThe number one resume mistake teachers make when applying for corporate jobsWhy the mind makes the money — and what to do when you believe it but don't fully trust it yetWhat it means to burn the ships and actually commit to your new life instead of just talking about itThis is the episode you send to every teacher in your circle who says they want more but keeps choosing the life they already have.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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086: The 5 Real Reasons Teachers Quit Their Transition Journey into Corporate
If you're a teacher who started your transition journey, got excited, and then slowly stopped without ever saying the words "I quit" — this episode is going to hit close to home.Because most teachers who give up don't call it giving up. They just stop doing the things that would have gotten them out, build a story around the stopping, and convince themselves they never really wanted to leave in the first place.In this episode, I break down the five real reasons teachers quit their transition journey — not the surface level excuses, but what is actually happening underneath.When you listen to this episode, you'll walk away with:Why burnout is the number one reason teachers never make it out — and why so many of them don't even know they have itThe difference between praying for a job and doing the work required to get oneWhat LinkedIn is actually doing to your mindset and how to stop letting it take you outWhy your ego might be the thing standing between you and a six figure job offerHow to recognize when you are quitting without admitting you are quitting — and what to do insteadThis is not tough love for the sake of it. This is the episode that keeps you in the game long enough to win.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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085: How to Leave a Career or Relationship That No Longer Serves You
If you're a teacher who knows something in your life is no longer working, but you can't seem to make yourself leave, this episode is for you.Whether it's a career, a relationship, or a situation you've outgrown, leaving is rarely about logistics. Most of the time, it's about fear, identity, familiarity, and the stories we tell ourselves about what we're capable of handling.In this episode, I share my own experience of leaving both a marriage and a career that no longer aligned with the life I wanted. We talk about why people stay longer than they should, why your brain confuses familiarity with safety, and how to move through the emotional process of choosing yourself.This is not about making impulsive decisions. It's about becoming aware of what is no longer serving you and having the courage to believe there is another door waiting for you.When you listen to this episode, you'll walk away with:Why your brain is keeping you stuck even when you know you want to goThe stages you will go through when you finally decide to leave — and why resistance is part of the process, not a sign to stopA journaling exercise to help you get out of your head and into your next chapterWhy you don't have to have it all figured out before you close the doorThe truth about what happens to women who finally choose themselvesThis is not a career strategy episode. This is the one that gets you ready for one. Because leaving is rarely easy. But staying somewhere that no longer serves you has a cost, too.You are allowed to choose a different future.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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084: Teacher Girlies, it's Time for a Pep Talk
In this episode, Jazmyne gets into the real reason teachers who want to leave… aren't leaving. Not the job market. Not the timing. Not the money. You.She breaks down the five stories teachers tell themselves that are quietly keeping them stuck, and why the "how" has never actually been the problem.When you listen to this episode, you'll walk away with the following knowledge:The difference between consuming the solution and actually doing the workWhy "I don't have time" and "I don't have money" are stories, not factsWhat fake progress actually looks like — and how to stop mistaking it for momentumA journal exercise to get honest about what is really making this feel hardThe only four things that actually matter when it comes to leaving the classroomIf you have been listening to every episode, following every tip, and still don't have a job offer — this episode is specifically for you.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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083: How Cassi Transitioned out of the Classroom and into EdTech Corporate
Fifteen years in the classroom. And one day, it just wasn't enough anymore.In Episode 83, Jazmyne sits down with Cassi, a former elementary educator who walked away from a 15-year teaching career and landed an EdTech corporate role. Not because it was easy. Because she stopped waiting for permission to want more.This isn't a feel-good story about following your passion. It's a real conversation about the fears that keep teachers stuck — retirement, benefits, identity, feeling "not qualified enough" — and what it actually takes to move through them.Jazmyne and Cassi breaks down:Why teachers struggle in corporate interviews (and how she fixed it)How she stopped selling herself as a teacher and started positioning as a professionalWhat life actually looks like without the Sunday scaries, the late-night lesson plans, and the emotional weight she didn't realize she was carryingIf you've been quietly thinking "I can't do this forever", then this episode is your answer.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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082: Why You're Getting Interviews (and NOT Job Offers) Part TWO
If you're a teacher who keeps getting interviews but still can’t seem to land the actual job offer, this episode is going to challenge the way you’re approaching your transition.In Part Two of this conversation, Jazmyne breaks down the deeper reasons teachers stay stuck in the interview cycle. Not because they aren’t qualified. But because they’re still showing up with the mindset, habits, and expectations that worked in education.This episode is about identity, discomfort, pressure, and the real skills required to successfully transition into corporate.When you listen to this episode, you’ll walk away with:Clarity on why interviews do not automatically equal job offersA deeper understanding of the mindset shifts required to transition successfullyEncouragement to stop avoiding discomfort and start building new skillsA reminder that rejection does not mean you are incapableAnd if you’re willing to become the version of yourself who can handle the pressure, receive feedback, and keep going anyway, your results will eventually catch up.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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081: Three Reasons to DIY your Career Transition vs Paying for Support
If you're a teacher who keeps going back and forth between figuring it out alone or getting help with your career transition, this episode is going to give you clarity.In this episode, Jazmyne Dionne breaks down the real reasons why some teachers successfully DIY their transition out of the classroom and why others stay stuck for months or years trying to do everything alone.Jazmyne shares her own transition story, what changed when she finally asked for help, and the mindset shifts teachers need if they want to move into EdTech, sales, customer success, or higher-paying careers outside the classroom.When you listen to this episode, you’ll walk away with:Insight into the difference between getting interviews and actually getting job offersA more honest view of what support, mentorship, and community can accelerateConfidence to stop seeing investing in yourself as something only other people can doA reminder that your teaching skills are valuable outside the classroomEncouragement to make decisions from possibility instead of fearYou do not have to stay stuck trying to prove you can do everything alone.Sometimes the fastest way forward is getting in the room with people who already know the path.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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080: Pretty, Paid, and in Tech: Customer Success Panel with Former Educators
If you've ever wondered what life actually looks like after the classroom — not the highlight reel, the real version — this episode is it.For the second time ever, you get to witness former teachers who left the classroom for higher paying corporate roles, all in one setting. This time? It's Customer Success.This is a real, unfiltered conversation with women who made the leap into EdTtech Customer Success roles and are now living lives they genuinely didn't think were possible while they were still teaching.You'll hear what a day in Customer Success actually looks like, why teachers are already built for it, and what happens when your nervous system finally gets to rest.When you listen to this episode, you'll walk away with:The realization that Customer Success is not a starting over — it's a transfer of everything you've already masteredA clear picture of what your day-to-day life could look like: no more 6am practices, no more sub plans, no more eating lunch in 12 minutesPermission to protect your peace, your process, and who you tell about your next moveThe truth that the hardest part of this transition isn't learning the job — it's believing you deserve a life outside of oneThis isn't about abandoning your purpose. It's about finding out what happens when you finally stop pouring everything into a system that was never designed to sustain you.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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079: Pretty, Paid, and in Tech: From Teaching to Six-Figure EdTech Sales Careers Panel
If you're a teacher who feels like your entire identity is wrapped up in your job… this episode is going to hit home.For the first time EVER, you will get to witness teachers who left the classroom for higher paying roles in one setting!This is a real conversation with former teachers who made the leap into EdTech Sales corporate roles and are now living lives they didn’t think were possible while they were in the classroom. They talk honestly about the fear, the grief, the doubt, and what actually changed on the other side.You’ll hear what it really looks like to leave, what they thought they would lose, and what they actually gained.When you listen to this episode, you’ll walk away with:The realization that you can miss teaching and still know it’s not where you belong anymoreA clear shift from “this is all I know” to “I have more options than I’ve been told”Permission to want a life that has energy, space, and time for you againThe truth that your skills were never the problem… you just haven’t been shown where they fitThis isn’t about hating teaching. It’s about being honest about what you want your life to look like now.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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078: How to Invest Thousands in your New Career on a Teacher Salary
If you're a teacher who keeps saying “I don’t have the money” but still wants a higher paying career, this episode is going to challenge you in a real way.We’re talking about what it actually looks like to invest in your next chapter on a teacher salary. Not from pressure, but from truth. Because the real barrier is not always your bank account. It is how you think about money, risk, and your future.This episode breaks down the mindset shifts that separate teachers who stay stuck from teachers who increase their income, along with real ways to approach investing when money feels tight.When you listen to this episode, you’ll walk away with:A clear understanding of why “I don’t have the money” keeps you stuckA new way to think about investing in yourself versus just spendingThe truth about what staying underpaid is actually costing youA perspective shift on becoming the version of you who earns moreConfidence to make decisions from your future, not your current situationYou don’t need everything figured out. You need to decide if you’re staying where you are or moving differently.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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077: The 7 Truths Transitioning Teachers Need to Hear to Leave the Classroom by August
If you're a teacher who keeps saying you want to leave the classroom but nothing is actually changing, this episode is going to hit.In Episode 77, Jazmyne Dionne breaks down seven uncomfortable truths about why teachers stay stuck even when they know they want more. This is not a step-by-step episode. This is the real conversation about identity, fear, safety, and the patterns that keep you choosing the same life.You’ll hear exactly why wanting to leave isn’t enough and what’s actually required if you plan to leave by August.When you listen to this episode, you’ll walk away with:The truth about the “teacher career pipeline” and where it actually leads if you stayWhy tying your identity only to teaching makes leaving feel almost impossibleHow your sense of safety is keeping you in a situation you say you’ve outgrownThe real reason you keep believing things that justify stayingWhy not believing in yourself is showing up in your actions, not just your thoughtsThis episode is direct for a reason.If you’ve been waiting for the right time, this is the moment you start telling yourself the truth.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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076: How to Know If You Would Be a Good Fit for EdTech Customer Success or Sales as a Transitioning Teacher
If you're a teacher who knows you want to leave the classroom but feels stuck choosing between EdTech customer success or sales, this episode will help you get clear.In this episode, we break down the real difference between these two career paths so you can decide which one actually fits you. Not just what sounds good, but what aligns with how you like to work, communicate, and solve problems.You’ll hear what each role looks like day to day, how they overlap, and what kind of person tends to thrive in each.When you listen to this episode, you’ll walk away with:Clarity on whether customer success or sales is the better fit for youA deeper understanding of how each role actually functionsConfidence in choosing a direction instead of staying stuck between bothInsight into how your personality and preferences impact your successRelief from feeling like you have to pick blindlyA clearer sense of what your next step should beYou shouldn't guess your way into your next career. You need to understand it well enough to choose it.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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075: What Roles You’re Actually Qualified for as a Teacher & How to Use Your Education Degree in Corporate
If you're a teacher who is wondering whether you would actually be a good fit to transition into corporate roles using your teaching background, this episode is for you.This episode is not about convincing you to leave. It is about helping you understand if this path makes sense for you and what it actually takes to succeed once you get there.When you listen to this episode, you’ll walk away with:A grounded understanding that your degree already qualifies you for corporate opportunitiesA shift from random job applying to a strategic career transition planA deeper belief that you are capable of succeeding outside the classroomA more honest way to approach burnout without ignoring it or rushing decisionsThe perspective that investing in yourself is part of building a different futureThis is about making a decision from clarity, not exhaustion.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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074: 5 Reasons to not Feel Bad About Leaving your Teaching Career
If you're a teacher who feels guilty even thinking about leaving the classroom, this episode is going to challenge that belief in a real and honest way.In this episode, Jazmyne Dionne breaks down why so many teachers feel stuck between burnout and guilt. She reframes what it actually means to leave teaching and why it is not something you need to apologize for. Through a powerful comparison and grounded truth, you will start to see your situation with more clarity and less shame.When you listen to this episode, you’ll walk away with:A sense of relief around wanting something different for your lifePermission to stop over-explaining your desire to leaveClarity that your impact does not end when you leave the classroomConfidence that choosing yourself is not selfishA shift in how you view your career and your optionsYou have already given so much. This episode will help you see what it looks like to give something back to yourself.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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073: How to Decide if you Should RENEW your Teaching Contract
If you're a teacher who is staring at your contract and feeling stuck between fear and possibility, this episode is for you.In this episode, Jazmyne Dionne walks you through how to actually make the decision to renew your teaching contract or not. Not from panic. Not from pressure. But from strategy, clarity, and self-trust. This is about understanding what the decision really means, and how to move in a way that protects your future.When you listen to this episode, you’ll walk away with:A grounded way to think about your contract decision without spiralingA mindset shift that helps you stop making decisions from fearA simple way to build belief in your ability to transition out of teachingA deeper understanding of why support and accountability change everythingConfidence to move at your own pace instead of rushing or forcing a timelineYou do not need to have everything figured out today. You just need to make your next decision from a place of clarity instead of fear. This episode will help you do exactly that.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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072: How to ACE your Corporate Interviews in 2026 as a Transitioning Teacher
If you're a teacher who is getting corporate interviews but not getting the offer, this episode is for you.The truth is simple. Most teachers are not struggling with getting interviews. They are struggling with how they interview.In this episode, Jazmyne Dionne breaks down the exact strategy she teaches her clients to help them confidently land corporate roles. From understanding the job deeply to communicating your value clearly, this episode focuses on the skills that actually move you from interview to offer.When you listen to this episode, you’ll walk away with:A clearer understanding of what companies are actually looking for in an interviewWhy knowing the job deeply is the foundation of a strong interviewJazmyne’s ACE method for answering interview questions clearly and confidentlyA mindset shift that helps you stop treating interviews like high-stakes pressure momentsHow to stand out from other candidates using individuality, contribution, and excellenceSimple ways to build rapport and break the ice with interviewersA practical approach to practicing interviews so you show up prepared, not nervousInterviewing is a skill. And when you learn how to communicate your value clearly, landing the job becomes a lot more possible.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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071: 7 Reasons Why You Haven't Landed the Interviews or Job Offers you Want as a Transitioning Teacher
If you're a teacher who keeps applying for jobs and wondering why you are not getting interviews or offers, this episode is for you.There are specific reasons you have not gotten the results you want yet. And most of them are fixable.In this episode, I walk through the 7 real reasons teachers struggle when transitioning into corporate roles. When you listen to this episode, you’ll walk away with:Clarity on what might actually be blocking your interviewsA shift from feeling rejected to feeling responsible and empoweredA better understanding of what hiring managers are really looking forA more strategic way to approach applications and interviewsPermission to invest in yourself instead of waiting to feel “ready”You are not stuck because you are incapable. You are stuck because something in your strategy or belief system needs to shift.Let’s fix that.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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070: How to NOT Burn Bridges as an Educator Leaving Education for Corporate
If you're a teacher who knows you are ready to leave the classroom but you are worried about damaging relationships on your way out, this episode is for you.Transitioning from education into corporate can feel complicated because you care about your students, you respect your colleagues, and you do not want your decision to be misunderstood. At the same time, you know that staying in a role that no longer fits you is not the answer.In this episode, I am walking you through how to leave education without burning bridges. I share my personal experience navigating this transition, what it looks like to plan your exit thoughtfully, and how to communicate your decision in a way that protects your reputation.When you listen to this episode, you’ll walk away with:Confidence that you can leave education professionally and respectfullyClarity on how preparation makes your exit smoother and less emotionalPeace knowing you can ensure your students are supported during the transitionPermission to prioritize your income and long term career growthA healthier mindset around maintaining relationships after you leaveLeaving does not have to mean conflict. It can mean growth handled well.This episode will help you think about your next move with maturity, strategy, and self respect.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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069: How to Transition into a New Career As a Teacher by Next School Year
If you're a teacher who keeps saying, “I need to be out by next school year,” but secretly has no idea how to make that happen… this episode is for you.In this episode of the Pretty Rich Teacher Podcast, I’m breaking down what it actually takes to transition into a new career by next school year. Not the fantasy version. The real version.We’re talking about what most teachers get wrong when they set exit timelines. Why skill development matters more than urgency. And why healing your burnout is not optional if you want to succeed outside the classroom.If you’re looking at EdTech or any corporate path and wondering where to start, this episode will ground you.When you listen to this episode, you’ll walk away with:Clarity on what it really takes to transition by next school yearPermission to be a beginner without feeling behindA reminder that asking for help is strategy, not weaknessThe belief that you can build a new career at any stageYou need a plan that builds capacity, not anxiety. Let’s get you transitioned the right way!Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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068: How to ask for what you deserve in your dating life and your career with Torah Cents
If you're a teacher who keeps over-giving in your career and your relationships and wondering why you still feel unseen, this episode is for you.In this conversation, I sit down with dating coach Torah Cents to unpack the quiet ways teachers settle. At work. In dating. In how we advocate for ourselves. We talk about burnout, good girl conditioning, and why so many teachers struggle to ask for more even when they have earned it.This episode is not about dating tips or career hacks. It is about self-trust, preparation, and building the courage to ask for what you actually want instead of accepting what shows up.When you listen to this episode, you’ll walk away with:A clearer understanding of how your dating patterns and career patterns mirror each otherPermission to stop settling just because something feels familiar or safeA new way to think about preparation instead of perfectionLanguage to ask for more without guilt or over-explainingA reminder that discomfort is not a red flag. It is often the doorwayValidation that wanting more does not make you ungrateful or unrealisticYou are allowed to want a career and relationships that meet you where you are now. This episode will help you start acting like it.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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067: What to Do If Your Career Transition Is Taking Longer Than Planned
If you're a teacher who thought you would already be out of the classroom by now, this episode is for you.In this episode of the Pretty Rich Teacher Podcast, I’m talking about what it really means when your career transition is taking longer than planned. Not in a motivational way. In a real, grounded way that acknowledges the emotional, financial, and mental weight of staying longer than you expected.We talk about timelines, persistence, fear, and the pressure teachers quietly carry when their exit plan doesn’t go as fast as they hoped. This episode is about learning how to keep moving without turning delays into self-doubt.When you listen to this episode, you’ll walk away with:Relief that you are not behind or brokenClarity around why timelines often create more pressure than progressPermission to stop making delays mean failureA grounded way to think about investing in yourself without guiltA reminder that belief and emotional regulation matter as much as strategyA stronger connection to your why when motivation feels shakyYour transition is not late. It’s unfolding. This episode will help you stay steady while it does.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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066: How Carla DIY'd her Transition into corporate as a transitioned teacher
If you're a teacher who knows you cannot stay in the classroom forever but also does not want to gamble your future, this episode is for you.In Episode 66, I sit down with Carla C. Whyte, a transitioned teacher who did not wait for permission, luck, or a perfect roadmap. She made a clear decision and built her corporate transition step by step. Carla shares what it actually looked like to leave education, how she reframed her experience, and the internal shifts required to show up confidently in a completely new world.This conversation is honest about the work. The mindset shifts. The patience. And the strategy it takes to move from teaching into corporate without losing yourself along the way.When you listen to this episode, you’ll walk away with:Belief that teachers really do belong in corporate rolesClarity on why strategy matters more than motivationA grounded understanding of how confidence shows up in interviewsPermission to stop underselling your experienceA realistic picture of what the job search process requiresReassurance that taking your time does not mean you are behindValidation that your skills translate, even if the language is differentA calmer, more intentional way to think about your next moveThis is not about rushing your exit. It is about making a smart one.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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065: What Actually happens your first 90 days as a transitioned teacher working in corporate
If you're a teacher who is thinking about leaving the classroom but secretly wondering what actually happens after you land the corporate job, this episode is for you.In Episode 65, I walk you through the real first 90 days as a transitioned teacher working in corporate. Not the highlight reel. Not the fear stories. The emotional reset, the culture shock, the peace, and the moments that make you realize how much you were carrying for so long.We talk about the PTSD many teachers don’t realize they’re operating with. We talk about learning how to feel safe at work again. We talk about time freedom, quiet calendars, and the discomfort that comes with peace when you’ve been in survival mode for years.This episode is about normalizing what you feel after the transition and helping you stop questioning whether you made the right decision.When you listen to this episode, you’ll walk away with:Relief that what you’re feeling is normalPermission to slow down and rebuild your sense of safetyA clearer understanding of how corporate work actually operatesConfidence navigating politics without losing yourselfAwareness of how to document your value without overworkingReassurance that your teacher skills absolutely transferA deeper trust that you are already successfulThis episode will help you settle into the freedom you worked so hard to create.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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064: What EdTech Hiring Managers are ACTUALLY looking for in transitioning teachers
If you're a teacher who keeps hearing that EdTech is a “natural next step” but you are not getting interviews or offers, this episode is for you.In this episode, I break down what EdTech hiring managers are actually looking for when they hire transitioning teachers. Not what we assume they want. Not what career coaches vaguely suggest. What they are truly screening for when they read your resume, review your portfolio, and sit across from you in an interview.We unpack how many teachers unintentionally block their own success by over explaining their classroom experience instead of positioning their transferable skills in a way EdTech understands.When you listen to this episode, you’ll walk away with:A clear understanding of what EdTech hiring managers are actually evaluating when they interview transitioning teachers.Confidence in how to position your teaching experience as relevant, hireable skills instead of over explaining your classroom background.Clarity on what you still need to learn or prove so you can stop guessing and start showing up as a strong EdTech candidate.This episode is not about motivation. It is about clarity. And clarity changes everything.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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063: The Top 10 Reasons Teacher Career Transitions FAIL and How to Succeed in 2026
If you’re a teacher who’s terrified of failing after leaving the classroom—or secretly worried that trying and not succeeding would be worse than staying—this episode is for you.In this episode, I’m talking honestly about failure what it actually looks like during a teacher career transition, why it’s unavoidable, and why avoiding failure is the fastest way to stay stuck. This is a real conversation about disappointment, shame, resilience, and choosing to keep going anyway.When you listen to this episode, you’ll walk away with:A shift in how you think about failure and what it really meansA sense of relief knowing you’re not “behind” or brokenPermission to stop waiting for confidence before you moveA deeper trust in yourself to figure things out as you goThe feeling of being grounded, steadied, and ready to keep goingIf you’re ready to stop making fear the decision-maker—and start moving forward even when it’s uncomfortable—this episode will meet you right where you are.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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062: Five Ways to GUARANTEE a Successful Transition Into Corporate as a Teacher
If you’re a teacher who knows you want out of the classroom but feels stuck in uncertainty, fear, or overthinking—this episode is for you. If you keep saying “I want to leave” but haven’t fully committed to the process yet, you need this conversation.In this episode of the Pretty Rich Teacher Podcast, I’m breaking down the five non-negotiable ways to guarantee a successful transition into corporate. This episode is about taking ownership, getting honest, and deciding that your next career move is not optional.When You Listen to This Episode, You’ll Walk Away With:A clearer sense of what really determines success in a career transitionA mindset shift that helps you stop waiting for certainty and start movingA stronger sense of personal responsibility and ownership over your next moveMore confidence navigating uncertainty without spiralingA renewed commitment to treating your transition as non-negotiableThere is nothing wrong with you for wanting more. But wanting more isn’t enough.When you’re ready to stop hoping it works out—and start moving like it will—this episode will meet you exactly where you are.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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061: How to Create Your Exit Plan Into Corporate as a Teacher in Less Than 30 Days
If you’re a teacher who knows you can’t keep doing this but you also don’t know where to start this episode is for you.In this episode of The Pretty Rich Teacher Podcast, I break down exactly how to create a realistic, strategic exit plan into corporate in less than 30 days—without panic-applying, guessing, or starting another degree.In This Episode, You’ll Learn:✨ How to build corporate knowledge so interviews stop feeling intimidating✨ The difference between wanting out and having an actual exit plan✨ How understanding career paths changes your resume and your confidence✨ Why burnout must be addressed before you transition—not after✨ How your teaching skills translate into corporate value (even if it doesn’t feel obvious yet)✨ What “doing the work” really looks like during a career pivot✨ Why clarity beats speed—and how to get bothAre you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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060: The Truth About Corporate Layoffs, Job Safety, and the Government Shutdown — What Transitioning Teachers Really Need to Know
In this episode of the Pretty Rich Teacher Podcast, we’re getting real about corporate layoffs, job safety, and the government shutdown — and what all of this actually means for transitioning teachers.If you’ve been scared to leave teaching because you think corporate isn’t “stable,” this is the episode you needed yesterday.You’ll walk away with:The truth about layoffs in BOTH education and corporate (and why neither path is as “safe” as teachers think).Why transitioning educators are more employable than they realize when they learn how to articulate their value.How to build six-figure skills that make you career-proof, layoff-proof, and recession-proof.The mindset shift that instantly reduces fear around job stability and replaces it with strategy.How to think about promotions, growth, and advancement from Day 1 in your corporate role.The power of continuous learning, reinvention, and believing in your ability to pivot at any time.This episode will help you stop waiting for job safety to be “given” to you — and instead learn how to create it for yourself.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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059: Why You’re Getting Interviews (But Not Job Offers) And How to Fix It
In this episode of the Pretty Rich Teacher podcast, Jazmyne Dionne breaks down one of the biggest misunderstandings educators have when they’re transitioning into corporate or EdTech roles: interviews and job offers are NOT the same thing — and they require two completely different skill sets.Inside this episode, Jazmyne explains the real difference between “interview ready” and “offer ready,” the mindset shifts that actually lead to job offers, and the exact mistakes that keep educators stuck in the classroom longer than they planned.In this episode you will learn:Why interviews don’t automatically turn into offersThe mindset gap most transitioning teachers don’t even realize they haveThe real reason so many educators feel “stuck” even when they’re applyingWhy confidence, identity, and self-belief matter just as much as your resumeWhy setbacks don’t mean you’re unqualified — they mean you need a new strategyIf you’re a teacher who knows you’re meant for more, this episode will help you think differently, prepare differently, and show up as the version of you who actually gets the job.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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058: How Jada became a standout EdTech CSM candidate with only 4 years of teaching experience
In this week's episode, I’m sharing how Jada became a standout EdTech CSM candidate with only four years of teaching experience. Her story is a reminder that when you know how to package your experience, you become undeniable. Her approach made her confident, clear, and prepared in ways most transitioning teachers never are.When you listen to this episode, you’ll walk away with:The mindset shift that helped Jada stop taking redirection personallyHow her CSM portfolio became her biggest advantage in interviewsThe simple structures she used to avoid burnout during her job searchWhat she did to stay grounded, positive, and focused through her transitionAnd the proof that you already have the skills — you just need the right strategy to make them stand outThis is a story that will make you feel capable, prepared, and ready to take your next step with confidence.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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057: Rich Teacher, P.O.U.R Teacher: The Mindset difference between being underpaid or paid well
In this episode, Jazmyne breaks down the REAL mindset keeping teachers underpaid, overlooked, and overwhelmed — and introduces P.O.U.R, the framework behind the P.o.u.r. Teacher Mindset.You’ll learn how these four patterns silently drain teachers financially, emotionally, and professionally — and how to step into the Rich Teacher Mindset, the identity that unlocks more money, more confidence, and more career options.If you’ve ever felt stuck, burnt out, or guilty for wanting more than teaching, this episode gives you both the language and the liberation.You will learn:✨ The emotional and financial cost of being a “P.O.U.R Teacher”✨ How burnout leads to desperate job decisions✨ The identity shift every Rich Teacher must make✨ How to rewire your thoughts about money, success, and worth✨ The mindset required to build a six-figure career beyond the classroomThis episode is your permission slip to stop shrinking and start receiving.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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056: How to Stop Being Ghosted by Recruiters as a Transitioning Teacher
If you’ve ever walked out of an interview feeling hopeful… only to hear nothing for days, weeks, or forever? This episode is going to change how you see your entire job search.Today we’re talking about “ghosting” — what it actually is, why it feels so personal for educators, and how to shift out of discouragement and into strategy, self-awareness, and emotional regulation so you can start getting actual job offers, not “great conversations.”In this episode, you’ll walk away with:A new perspective on “ghosting” that puts you back in controlThe real interviewing skills you need to developHow to stop personalizing recruiter silenceThe mindset + emotional regulation needed to stay consistent in your job searchPractical next steps to increase your job offersIf you enjoyed this episode, you’ll love: ✨ Episode 55: “Rejection Sensitivity” ✨ Episode 45: “How to Choose Freedom Over Fear”Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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055: Rejection Sensitivity: What It Really Means for High-Achieving Teachers in Transition
In this episode, Jazmyne gets real about rejection sensitivity especially for high-achieving women navigating their career transition. If you’ve ever felt that familiar gut punch after a “thank-you-for-applying” email, this one’s for you. Jazmyne unpacks why rejection hits harder for those used to excelling, and how to turn those moments into data, direction, and deeper belief.What You’ll Learn when you listen:Why rejection sensitivity shows up more for high-achieversHow to view redirection emails as part of your success dataThe role of belief and emotional regulation in your job searchHow tracking applications turns emotion into evidenceThe mindset shift to stop fearing “no” and start expecting “next”Whether you’re applying for EdTech, corporate learning, or customer success roles, this episode will help you regulate your emotions, track your progress with confidence, and reframe every rejection as proof that you’re still in the game.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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054: The Scary Truth About Staying ‘One More Year’ (Why It Gets Harder, Not Easier)
In this episode, Jazmyne exposes the hard truth behind the phrase every burned-out teacher says: “I’ll just stay one more year.” She breaks down why staying stuck only deepens exhaustion, delays growth, and costs you opportunities — both emotional and financial. ✨ You’ll learn:Why staying “one more year” makes burnout worse, not betterHow to stop future-faking your happiness and start taking real actionThe hidden cost of contracts and misplaced loyaltyHow to separate your identity from your job titleSteps to start marketing your skills while you’re still teachingWhy leaving a toxic environment is an act of self-respect and serviceAfter listening to this episode, you’ll finally understand why waiting for “next year” only keeps you stuck — and how to choose courage, clarity, and freedom this year instead.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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053: How to Heal the Sunday Scaries (for Good)
In this episode, Jazmyne dives into one of the most common — and painful — experiences teachers face: the Sunday Scaries. She unpacks what’s really happening beneath the anxiety, exhaustion, and dread that hit before a new week, and shares how to begin healing it for good. ✨ You’ll learn:What the Sunday Scaries actually are and why they hit so hardHow to journal through your Sunday thoughts to release anxietyWhy normalizing burnout keeps you stuckThe truth about your power to choose a peaceful careerHow to shift from “trapped” to “in control” through mindset workSimple ways to set boundaries and protect your peaceWhy your future self will thank you for choosing rest over worryAfter listening to this episode, you’ll finally stop dreading Sundays — and start believing that peace is possible, even before Monday begins.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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052: How to Choose Freedom over Fear as a Veteran Teacher thinking about Transitioning out of the classroom
In this episode, Jazmyne speaks directly to veteran teachers who feel torn between loyalty and liberation. She opens up about her own journey, the burnout cycle that keeps seasoned educators stuck, and what it really means to choose freedom over fear. You’ll also learn her powerful H.E.A.L. framework to help you release guilt, rebuild identity, and rediscover who you are beyond the classroom.✨ You’ll learn:Why veteran teachers often feel trapped by a system that no longer serves themHow burnout can quietly become a lifestyle — and how to break the cycleWhat it means to honor your teaching experience without clinging to itThe four steps of the HEAL framework for moving forward with peaceHow to rebuild confidence and trust yourself againWhy choosing freedom doesn’t mean abandoning your callingAfter listening to this episode you will also walk away knowing that freedom isn’t selfish. It’s the most powerful act of self-trust you can make!Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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051: The Truth About Fear: Why Leaving Teaching Feels So Scary
In this episode, Jazmyne breaks down why leaving teaching feels so scary — even when you know it’s time. She dives into the fears of starting over, financial uncertainty, and the emotional guilt that keeps teachers stuck, showing you how to reframe fear as growth and build trust in your next chapter.✨ You’ll learn:What fear is really trying to tell youHow to release guilt about leaving your studentsWhy fear doesn’t mean stop — it means you’re growingThe truth about corporate life (it’s not as scary as it seems)How to trust yourself through uncertaintyA simple mindset shift to turn fear into forward motionAfter listenting you will learn that fear isn’t the enemy — it’s your invitation to grow.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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050: The 5 Core Skills That Will Get You Hired Fast as a Transitioning Teacher
In this episode of the Pretty Rich Teacher podcast, I’m revealing the five core skills that helped me — and my clients — land interviews and offers fast.If you’ve been stuck waiting for your “big break,” this is your wake-up call. Career transitions aren’t about luck — they’re about skills. And when you master these five, you’ll stand out instantly in the same job market that people claim to be "impossible to land a job in".You’ll learn how to:Develop career skills that make you an obvious hire — even without prior corporate experienceMarket yourself like a pro so your resume and LinkedIn actually get noticedSell your skills with confidence in interviews (no more underselling your experience)Network the right way — with genuine connections, not copy-paste DMsBuild the discipline and consistency that separate dreamers from doersI also walk you through how the Six-Figure Educator Certification + Mentorship gives you the roadmap to put these skills into action, so you can land your dream EdTech Customer Success, or Sales role without guessing what to do next.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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049: Why I Hired a Career Coach (Even After DIY’ing My Transition)
In this episode of the Pretty Rich Teacher podcast, I’m getting real about something I don’t think enough educators talk about — the moment I realized I couldn’t DIY my career transition anymore.If you’ve been grinding on applications, rewriting your resume 15 times, or feeling like “maybe it’s just not my time yet,” this one’s for you. I’m pulling back the curtain on why I decided to hire a career coach even after I thought I could do it all myself — and how that single decision changed everything about how I show up, sell my skills, and get paid what I’m worth.You’ll learn how to:Recognize when doing it alone is keeping you stuck in circlesShift from “I can figure it out” to “I deserve expert support”Understand what career coaches actually do — and how to spot the real ones from the scamsMarket your transferable skills like a pro, even if you’ve never worked outside of educationReframe investing in a coach as the smartest (and fastest) way to make more moneyThis episode is for the high achiever who’s tired of playing small, overthinking every move, and wondering why “hard work” still isn’t translating into job offers. Sometimes, the smartest move isn’t working harder — it’s hiring help.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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048: How to Actually Use LinkedIn to Land a 6-Figure Role
In this episode of the Pretty Rich Teacher podcast, we’re talking about one of the biggest mistakes I see teachers make when trying to pivot into EdTech or corporate...If you’ve been posting your job search struggles, over-sharing about burnout, or thinking you HAVE to post on LinkedIn every week to get hired, this episode is for you. I’m breaking down the difference between being an influencer and being a career seeker, and why mastering that difference could be the exact thing that helps you land a six-figure offer faster.You’ll learn how to:Position yourself as a career-ready professional — not a teacher trying to escape the classroomShift your mindset from “posting for validation” to “showing up for opportunities”Craft a LinkedIn profile that actually attracts recruiters (and makes them message you)Network intentionally and build genuine relationships with hiring managersAvoid the rookie mistakes that silently disqualify amazing educators every dayBy the end, you’ll know exactly how to use LinkedIn as your six-figure launchpad, not your diary.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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047: Resume Writer vs. Career Coach vs. DIY: What You Actually Need to Land the Job
I’m breaking down one of the biggest questions teachers ask when they’re ready to leave the classroom — “Should I hire a resume writer, work with a career coach, or just figure it out myself?”If you’ve been stuck updating your resume for weeks, scrolling job boards at midnight, or wondering what’s actually worth investing in — this episode is for you. I walk you through the real difference between DIY, resume writers, and career coaches, and how to know which one fits your stage of transition.You’ll learn how to:Define what you actually want in your next role (before you waste time applying to everything)Understand the job market and why EdTech and corporate roles are ideal for former educatorsMaster the mindset needed to make a real career pivot — not just another job searchSpot the difference between polished documents and a real job strategyDecide when it’s time to stop guessing and start getting professional guidancePlus, I share what’s worked for me and my clients — including how investing strategically in your career transition can literally be the move that gets you paid more, faster.This isn’t just about resumes or coaching — it’s about building a plan that gets you interviews, confidence, and clarity.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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046: How Ashley ( A Guidance Counselor) Let Go of Her Timeline and Landed Her Dream EdTech Role
In this episode, Jazmyne sits down with her client Ashley, who shares her journey of transitioning from a 16-year career in education to landing her dream EdTech sales role.Ashley opens up about ending her contract without a job lined up and the moment she stopped obsessing over her timeline and started building the skills that would make her irresistible to hiring managers. Her story proves that even when the path gets messy, focusing on skills over timelines is what collapses the gap between where you are and where you want to be.✨ Here's what you'll walk away with when you listen:Why letting go of your timeline is the breakthrough you needThe power of lifetime access and coaching support in landing your offerNetworking and interviewing strategies that work for educatorsWhat to do when you hear "no" and why it doesn't mean stopHow to become the role before you land itWhether you've been teaching 2 years or 20, Ashley's story will show you that it's never too late—even if you've already tried once.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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045: How To Make Six Figures as an Educator with a Victory Mindset
In this episode, Jazmyne discusses the importance of shifting into a victory mindset, particularly for women in education seeking to transition into six-figure careers.She introduces a powerful framework that reveals three roles we unconsciously play that keep us stuck—and how recognizing these patterns is the key to breaking free.✨ Here's what you'll walk away with when you listen:A transformational framework that reveals exactly how you're showing up in your transitionWhy "waiting for the right opportunity" is actually keeping you comfortable (not ready)How to step into a victory mindset through self-observation and awarenessThe power of radical ownership in accelerating your career transitionWhy embracing your power and privilege is the secret to your six-figure journeyIf you've been applying but not landing interviews—or you're afraid you'll be stuck in education forever—this episode will show you exactly what needs to shift.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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044: From Fear to Freedom: Funké’s Journey from Veteran Teacher to New EdTech Career in less than 60 Days
In this week’s episode Funké shares how resilience, mentorship, and self-belief helped her navigate the messy middle of her career transition and step into a whole new chapter of life.As a veteran teacher, she could have told herself it was too late. She could have let interview fears and self-doubt keep her stuck. But instead, she chose to stay open—open to therapy, open to mentorship, and open to believing she was stronger than her fears.✨ Here’s what you’ll walk away with when you listen:Why showing up for yourself matters more than being “perfect”How resilience and therapy can move you through seasons of doubtWhy mentorship is a shortcut to confidence and clarityHow self-worth shifts everything about the way you interview and applyProof that it’s never too late to rewrite your storyFunké’s journey is more than a career change, it’s a reminder that your strength grows every time you choose to show up, even when it’s uncomfortable.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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043: How to become Classroom Optional
What does it actually mean to be classroom optional—and how do you get there for good?In this episode Jazmyne unpacks the two real reasons educators go back to the classroom after landing a corporate role: because they want to, or because they feel they have no other choice. While both are valid, Jazmyne reveals why the true goal is freedom—and that comes from being classroom optional.By the end of this episode, you’ll know exactly how to:Reframe the classroom as a choice rather than a fallback planBuild the skills that give you long-term security in corporate spacesLeverage your teaching experience as a superpower in interviews and rolesCreate career options beyond education so you’ll never feel trapped again✨ This isn’t just about leaving teaching it’s about stepping into a life where you’ll always have options, and teaching is one of them, not your only one.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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042: Two Years In: Jasmine’s Pivot from the Classroom to Career Freedom
In this episode, Dr. Jazmyne sits down with Jasmine, a young teacher who chose to pivot after just two years in the classroom. Together, they explore what it means to walk away from teaching early in your career, how to navigate the fear of the unknown, and why mindset is the foundation for any big life change.Jasmine shares her journey of embracing discomfort, reframing negative thoughts through thought scripts, and learning to see feedback as a gift instead of criticism. She opens up about the duality of independence — how you can be strong and self-sufficient while also receiving help — and why gratitude has been key in softening the pressures of building a new career.By the end of this conversation, you’ll walk away with:A new perspective on fear and how to use it as fuel for growthThought scripts to reframe negative beliefs and boost confidenceA mindset shift that positions sales as an extension of teaching and connectionA reminder that asking for help is strength, not weaknessA practical way to use feedback and gratitude to accelerate personal growthThis episode is a must-listen for any teacher — whether you’re two years in or twenty — who’s ready to explore what’s possible beyond the classroom!Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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041: How to Heal Timeline Heartbreak
In this episode of the Pretty Rich Teacher podcast, Dr. Jazmyne Dionne opens up about something so many high-achieving women feel but rarely say out loud: timeline heartbreak.If you’ve ever whispered to yourself, “I should be further along by now,” this episode is for you. If you’ve circled birthdays, school years, or New Year’s deadlines on your calendar and felt crushed when life didn’t match the plan — this episode is for you. If you’ve ever scrolled past someone else’s success and thought, “Why not me, yet?” this episode is for you.Jazmyne shares her own stories of chasing deadlines that didn’t pan out and the heartbreak that comes with it. But she also gives you the reframes you need:Why missing your “timeline” isn’t failure — it’s redirection.How to focus on building skills, not just chasing dates.Simple mindset shifts that will help you breathe easier when the clock doesn’t match your calling.Permission to stop hustling for someone else’s version of “on time” and start owning your own pace.Press play and let this conversation remind you: you are not behind. You’re right on time.Are you a burnt out educator looking to leave the classroom but don't know where to start? Click here to enroll in my DIY Exit Plan Course.Are you a burnt out women in education ready for 1:1 mentorship, a custom 100K Career Plan + an additional stream of income? click here book a free 1:1 sales call to learn how to use your teaching experience to make 100k and beyond! On our call will personally map out how to make your 6K back in less than six months!Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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ABOUT THIS SHOW
Welcome to the Pretty Rich Teacher podcast (formerly known as the Exit Plan) where Jazmyne shares exclusive tips to help women in education turn their teaching experience into six figure careers and beyond with confidence.
HOSTED BY
Dr. Jazmyne Dionne
CATEGORIES
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