Pretty Rich Teacher

Episoade

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  094: You Don’t Have to Wait for Life to Get Easier to Leave the Classroom | Keysha’s 4 Month Edtech Transition Story 14.08.2026 1h 48min

  If you're a teacher who keeps telling yourself, “I’ll leave when life calms down,” this episode is for you.In this episode, Keysha is sharing her incredible 4-month transition from the classroom into an EdTech role. What makes her story so powerful is not that everything was easy. It’s that she decided to move forward before life felt perfectly organized, perfectly certain, or perfectly timed.This episode is a reminder that waiting for the “right time” can quietly keep you stuck far longer than you realize.When you listen to this episode, you’ll walk away with:The confidence to stop waiting for perfect timing before pursuing a new career.A new perspective on what is actually required to transition out of teaching.Permission to move forward even when life still feels busy, uncertain, or messy.Hope that a corporate transition can happen faster than you think.If you’ve been wondering whether your circumstances are “good enough” to start, let Keysha’s story show you what’s possible.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  093: The 4 Reasons Teachers Aren’t Using Their Experience to Make $100K 07.08.2026 31min

  If you're a teacher who knows you're capable of more but can't figure out what's keeping you stuck, this episode is for you.You may think you need a better resume or more experience. But what if that's not the real reason you haven't landed the career you want?In this episode, I'm sharing the four biggest blockers I see keeping teachers from turning their experience into six figure opportunities.In this episode, you'll walk away with:Clarity on what's really holding you back.A new way to think about your career transition.More confidence to move forward.The motivation to take your next step.Sometimes the biggest obstacle isn't your experience. It's what you believe about it.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  092: How to beat the back to school blues 4 steps to creating a pretty rich exit plan that actually works 31.07.2026 50min

  If you're a teacher walking back into the classroom wondering why you're still there, this one's for you.Back-to-school season makes you question yourself — maybe you promised this would be your last August, maybe you feel guilty for not having a corporate offer yet, or maybe you're excited to meet your students but still know you don't want another year in education. Both can be true.In this episode, I share the four-step framework I use with teachers to stop the self-judgment, pinpoint what's actually keeping them stuck, and build an exit plan they can follow with confidence instead of guilt. I'll also introduce a new resource to help you identify the biggest blocker between you and your next career.You'll walk away with:A healthier way to view your transition, without treating your current situation as failure.A simple process to find what's really stalling your exit plan.A new lens on letting your emotions guide your next move instead of controlling it.More confidence that the right support can still get you there.The classroom may be where your school year starts. It doesn't have to be where your story ends.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  091: How Caylin DIY-ed Her Teacher Exit Into EdTech in Less Than 4 Months as a Single Mom 24.07.2026 48min

  If you're a teacher who feels like you're missing the moments that matter most because your career is taking everything you've got, this episode is for you.This week, I'm joined by Caylin, a former middle school science teacher and single mom who transitioned into EdTech in less than four months using the DIY Exit Plan.Caylin shares the mindset shifts that changed everything, how she navigated burnout, why she chose Customer Success, and what it looked like to confidently interview her way into an EdTech role while still finishing the school year strong.When you listen to this episode, you'll walk away with:Clarity on what the teacher to corporate transition can actually look like.A new perspective on investing in your own future.Clarity on what the teacher to corporate transition can actually look like.A reminder that the biggest obstacle to your next chapter may simply be believing you're capable of it.Your exit doesn't start with the perfect resume. It starts with believing your life can look different.Tune in and let Caylin's story remind you what's possible.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  090: Putting Herself First: From Assistant Principal to Customer Success 16.07.2026 57min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  089: How Lauren Got Six Figures, Lost 15 Pounds, and Started a Business in 90 Days 10.07.2026 44min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  088: How to be Swimming in Interviews + Job Offers this Summer 03.07.2026 39min

  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 summerWant to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  087: Teacher to Corporate: The Story Behind My Six-Figure Career Pivot 26.06.2026 1h 1min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  086: The 5 Real Reasons Teachers Quit Their Transition Journey into Corporate 19.06.2026 29min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  085: How to Leave a Career or Relationship That No Longer Serves You 12.06.2026 38min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  084: Teacher Girlies, it's Time for a Pep Talk 05.06.2026 49min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  083: How Cassi Transitioned out of the Classroom and into EdTech Corporate 29.05.2026 40min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  082: Why You're Getting Interviews (and NOT Job Offers) Part TWO 22.05.2026 47min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  081: Three Reasons to DIY your Career Transition vs Paying for Support 15.05.2026 35min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  080: Pretty, Paid, and in Tech: Customer Success Panel with Former Educators 08.05.2026 1h 35min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  079: Pretty, Paid, and in Tech: From Teaching to Six-Figure EdTech Sales Careers Panel 01.05.2026 1h 25min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  078: How to Invest Thousands in your New Career on a Teacher Salary 24.04.2026 46min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  077: The 7 Truths Transitioning Teachers Need to Hear to Leave the Classroom by August 17.04.2026 1h 1min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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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 10.04.2026 40min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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  075: What Roles You’re Actually Qualified for as a Teacher & How to Use Your Education Degree in Corporate 03.04.2026 58min

  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.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? click here book a free 1:1 sales call to learn how to enroll in my Teachers in Tech mentorship + certification program.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.