
Advertise on podcast: Pretty Rich Teacher
Rating
5from
This podcast has
104 episodes
Language
EnglishPublisher
Dr. Jazmyne DionneExplicit
No
Date created
2024/12/14
Latest episode
2026/10/23
Average duration
50 min.
Release period
8 days
Description
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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Check latest episodes from Pretty Rich Teacher podcast
104: What is edtech and how do I standout to get hired as a teacher?
2026/10/23
If you're a teacher who wants to leave the classroom, earn more money, and explore a corporate career without throwing away the experience you've spent years building, this episode is for you.
EdTech, short for educational technology, could be a way to continue supporting education while building a career outside the classroom.
But how do you break into the industry, and what does it actually take to get hired?
In Episode 104 of the Pretty Rich Teacher Podcast, Dr. Jazmyne Dionne breaks down what EdTech is, why it can be a promising career path for educators, and two roles worth exploring: EdTech Customer Success and EdTech Sales Consulting.
She also explains why having years of teaching experience isn't always enough to stand out in a competitive job market. The difference is learning what employers need, understanding the role you're pursuing, and showing them how your experience can solve real business problems.
When you listen to this episode, you'll walk away with:
A clearer picture of how your teaching experience can translate into a career in EdTech.A new perspective on Customer Success and Sales Consulting as potential paths beyond the classroom.A better understanding of what separates a qualified candidate from someone an employer feels confident hiring.The confidence to see your existing skills as a foundation for a new career, not something you have to leave behind.
You have already proven that you can learn, lead, communicate, and solve problems. Now it's time to learn how to use those strengths in a different environment.
Your next career chapter doesn't have to erase your teaching experience. It can build on it.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
103: She did it scared: how support helped Jae (a new mom) land a new role in less than two months
2026/10/16
If you're a teacher who wants to leave the classroom but feels scared to start over, this episode is your reminder that you don't have to have it all figured out to take the next step.
In Episode 103 of the Pretty Rich Teacher Podcast, Jazmyne sits down with Jae, a former classroom teacher and new mom who landed her first EdTech account manager role in less than two months.
Jae shares how she approached her career transition, navigated multiple rounds of corporate interviews, and leaned on the support and resources available to her while learning a completely different hiring process. She also opens up about the mindset that helped her keep moving forward, even when she didn't know what would happen next.
Her story is a reminder that you don't have to wait until you're completely burned out to choose something different. You can love parts of teaching and still want more flexibility, more time with your family, and a career that better fits the life you're building.
When you listen to this episode, you’ll walk away with:
A reminder that you can take action even when you're scared or uncertain about what comes next.A renewed appreciation for the skills and experience you already bring to a new career.The confidence to approach your career transition as a learning process instead of a test of your worth.Encouragement to build a career that gives you more room to be present for yourself and the people you love.
You don't have to feel completely ready before you begin. Sometimes, you just need the right support, a willingness to learn, and the courage to take the 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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
102: Scared to leave your students? Yaya shares the truth about life one year after teaching
2026/10/09
If you're a teacher who loves your students but knows you can't keep sacrificing your health, energy, time, and life for the classroom, this episode is for you.
In Episode 102, I sit down with Yaya, a former teacher and Pretty Rich Teacher alumni who made the transition from teaching into a fully remote ed tech career.
One year after starting her transition, Yaya's life looks completely different. But getting there wasn't instant or easy. She had to work through guilt, rejection, fear, uncomfortable feedback, and the grief that came with closing one chapter of her life.
More importantly, she had to learn that choosing herself didn't mean she stopped caring about her students.
When you listen to this episode, you'll walk away with:
A deeper belief that there can be a full, beautiful life waiting for you outside the classroom.Permission to care about your students without making their needs more important than your own.A reminder that rejection, uncertainty, and uncomfortable emotions don't mean you're on the wrong path.The confidence to see your teaching experience as something you can carry into an entirely new career.
Your students don't disappear just because you leave the classroom.
And neither should you.
Sometimes choosing yourself is the thing that allows you to finally become the version of yourself you've been trying to get back to.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
101: How a Private School Teacher Became an EdTech Customer Success Manager & Made Back $4K in 30 Days
2026/10/02
If you're a teacher who knows you want more but keeps telling yourself that leaving the classroom is too risky, this episode is for you.
In Episode 101, I’m sitting down with my client Deyaneira to talk about what it really looked like for her to leave private school teaching and transition into an EdTech Customer Success Manager role.
Her story is about more than landing a new job. It’s about learning to trust yourself, getting comfortable with being uncomfortable, and realizing that the career you have does not have to be the career you keep.
Deyaneira shares what changed when she stopped waiting to feel ready, invested in learning a new career, and decided that rejection would not be the reason she stopped moving forward.
When you listen to this episode, you’ll walk away with:
A renewed belief that you are capable of creating a different career path.The courage to stop confusing comfort with fulfillment.A reminder that rejection does not determine your value or your future.Permission to bet on yourself and build a life that gives you more time, freedom, and peace.
You don't have to have your entire future figured out before you move.
Sometimes you just have to decide that the life you're living is no longer the life you're willing to settle for.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
100: 10 Lessons From Making 100K as a Transitioned Teacher
2026/09/25
If you're a teacher who knows you're meant for more but still finds yourself questioning whether you can actually leave the classroom, this episode is for you.
Episode 100 is a celebration, but it is also a reflection on what it really took to build a six-figure life after transitioning out of the classroom.
In this episode, Jazmyne shares 10 lessons she learned from making $100K+ as a transitioned teacher.
From learning to trust yourself and being intentional about whose advice you listen to, to accepting that the next chapter may be hard and choosing to do it anyway, these lessons are about more than money.
They're about becoming the woman who no longer waits for permission to create a different life.
When you listen to this episode, you’ll walk away with:
A deeper belief that your life can look different from what you were taught to expect.More clarity around the mindset shifts that can help you move beyond good girl teacher conditioning.Permission to stop needing everyone around you to understand your next move.A stronger reminder that you are capable of becoming the person you have been waiting for.
Leaving the classroom may not be easy. But neither is staying somewhere that no longer fits who you are becoming.
You don't have to have everything figured out. You just have to be willing to trust yourself enough to take the next step.
And remember, you're really pretty.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
099: How to Get the Support You Need to Transition Into a Six Figure Career for Real This Time
2026/09/18
If you're a teacher who has been saying, "I want to leave the classroom," for months or even years, but somehow you keep finding yourself back in the same place, this episode is for you.
In Episode 99, Jazmyne gets real about what it actually takes to transition into a six-figure EdTech career for real this time. She also challenges the beliefs that can keep teachers stuck, including feeling like you need another degree, worrying about leaving your retirement or students, or believing you should be able to figure it all out yourself.
Sometimes the problem isn't that you don't want it badly enough. You may simply be trying to figure out too much on your own.
When you listen to this episode, you'll walk away with:
A clearer picture of what becomes possible when you stop trying to make the transition aloneMore confidence in your ability to take your teaching experience into a six-figure careerA new perspective on the time and emotional cost of staying stuckA reminder that getting support isn't a weakness. It can be the thing that finally helps you move
Your next chapter can be different. You need to give yourself the support to actually make the transition.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
098: How Angelica Turned Less Than Four Years of Teaching Into a Six-Figure Career
2026/09/11
If you're a teacher who loves your students but knows deep down that you want more from your life, Angelica's story is one you need to hear.
After just four years in the classroom, Angelica made the decision to explore what was possible outside of teaching. She was burnt out, but she was also comfortable. She had questions about whether her teaching experience was enough to build a new career, and she had plenty of fears about making the transition.
Today, Angelica is working in ed tech sales, earning six figures, with more flexibility, more time freedom, and a completely different relationship with work.
In this episode, Angelica shares what it really looked like to go from a first grade classroom to a six-figure corporate career.
When you listen to this episode, you’ll walk away with:
A reminder that you are not as limited by your teaching experience as you may think.More confidence in what could be possible on the other side of the classroom.Perspective on why a slower transition does not mean you're failing.Encouragement to stop ignoring the part of you that knows you want something different.
Sometimes the first step is simply being honest with yourself about what you want next.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
097: From Music Teacher to Customer Success: Proof You Can Pivot Into Edtech No Matter What You Teach
2026/09/04
If you're a teacher who has no problem spending money on your classroom, your students, or another degree, but suddenly freeze when it comes to investing in yourself, this episode is for you.
In Episode 97 of the Pretty Rich Teacher Podcast, Jazmyne sits down with Tammy, a former music educator of 15 years who made multiple career pivots before landing in the corporate world.
Tammy shares what changed when she stopped thinking about leaving education as simply finding another job and started approaching it as a career change. They talk about the discomfort of investing in yourself, why teachers are conditioned to sacrifice, and what it looks like to believe that a different life is actually possible.
Most importantly, this conversation is about more than getting a new job. It is about learning to see yourself differently.
When you listen to this episode, you’ll walk away with:
A deeper belief that you are capable of creating a career and life that actually fit who you are now.Permission to stop measuring your worth by how much you sacrifice for everyone else.A new perspective on investing in yourself as a way to close the gap between where you are and where you want to be.The reminder that change is possible, even when you don't know exactly how you're going to get there yet.
You don't have to know every step before you give yourself permission to want something different.
Sometimes the first step is simply believing, "Why not me?"
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
096: 7 Thoughts Making It Hard to Break Into Edtech as a Teacher
2026/08/28
If you're a teacher who wants to leave the classroom but keeps finding yourself stuck in the same place, it may not be your experience, your resume, or even the job market holding you back. Sometimes, it is the thoughts you have about what it takes to make the transition.
In this episode, Jazmyne breaks down 7 thoughts that can make breaking into Edtech feel harder than it actually is.
You’ll also hear a powerful reminder that leaving the classroom does not mean starting from zero. Your experience as an educator can become an advantage in a new career.
When you listen to this episode, you’ll walk away with:
A new perspective on the beliefs that may be keeping you stuckMore confidence in the value of your experience outside the classroomClarity around why your career transition may feel harder than it needs toA renewed belief that a six-figure career in edtech can be possible for you
You do not have to keep repeating the same thoughts and expecting a different result.
Sometimes the first step toward a different career is simply being willing to think differently about what is possible for you.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
095: Teachers, Let’s Talk About Money: The Money Conversation ALL Educators Need to Hear.
2026/08/21
If you're a teacher who wants to make $100K beyond the classroom but feels like money is something you were never taught to understand, this episode is for you.
In Episode 95, Jazmyne sits down with her money coach, Aqura, for the conversation every teacher needs to hear about money, income, and what it actually takes to create more financial options.
This is not just about making more money. It's about understanding why you may feel stuck, why another degree isn't always the answer, and what happens when you start feeling safe enough to make different decisions with your money.
When you listen to this episode, you’ll walk away with:
A new perspective on what may actually be keeping you from your next income level.More clarity around the difference between feeling financially safe and simply staying with what feels familiar.Permission to consider investing in yourself and your earning potential differently.A stronger belief that you can learn how to create more money, even if you were never taught how.
You don't have to have every answer today. But you do get to start having a different conversation with yourself about money.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
094: You Don’t Have to Wait for Life to Get Easier to Leave the Classroom | Keysha’s 4 Month Edtech Transition Story
2026/08/14
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.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
093: The 4 Reasons Teachers Aren’t Using Their Experience to Make $100K
2026/08/07
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.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
092: How to beat the back to school blues 4 steps to creating a pretty rich exit plan that actually works
2026/07/31
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.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
091: How Caylin DIY-ed Her Teacher Exit Into EdTech in Less Than 4 Months as a Single Mom
2026/07/24
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.
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?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
090: Putting Herself First: From Assistant Principal to Customer Success
2026/07/16
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 women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days?
Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.
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.
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.
Podcast reviews
Read Pretty Rich Teacher podcast reviews
J-Doll 2025/12/23
Strategies and Confidence Found
I have begun my journey into EdTech and this podcast is helping me feel prepared. It is the confidence booster and point in the right direction needed...
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