Pretty Rich Teacher

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 professional
• What life actually looks like without the Sunday scaries, the late-night lesson plans, and the emotional weight she didn't realize she was carrying

If you've been quietly thinking "I can't do this forever", then this episode is your answer.

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.

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 offers
• A deeper understanding of the mindset shifts required to transition successfully
• Encouragement to stop avoiding discomfort and start building new skills
• A reminder that rejection does not mean you are incapable

And 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 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.

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 offers
• A more honest view of what support, mentorship, and community can accelerate
• Confidence to stop seeing investing in yourself as something only other people can do
• A reminder that your teaching skills are valuable outside the classroom
• Encouragement to make decisions from possibility instead of fear

You 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 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.

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 mastered
• A 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 minutes
• Permission to protect your peace, your process, and who you tell about your next move
• The truth that the hardest part of this transition isn't learning the job — it's believing you deserve a life outside of one

This 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 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.

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 anymore
• A 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 again
• The truth that your skills were never the problem… you just haven’t been shown where they fit

This 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 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.

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 stuck
• A new way to think about investing in yourself versus just spending
• The truth about what staying underpaid is actually costing you
• A perspective shift on becoming the version of you who earns more
• Confidence to make decisions from your future, not your current situation

You 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 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.

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 stay
• Why tying your identity only to teaching makes leaving feel almost impossible
• How your sense of safety is keeping you in a situation you say you’ve outgrown
• The real reason you keep believing things that justify staying
• Why not believing in yourself is showing up in your actions, not just your thoughts

This 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 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.

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 you
• A deeper understanding of how each role actually functions
• Confidence in choosing a direction instead of staying stuck between both
• Insight into how your personality and preferences impact your success
• Relief from feeling like you have to pick blindly
• A clearer sense of what your next step should be

You shouldn't guess your way into your next career. You need to understand it well enough to choose 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.

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 opportunities
• A shift from random job applying to a strategic career transition plan
• A deeper belief that you are capable of succeeding outside the classroom
• A more honest way to approach burnout without ignoring it or rushing decisions
• The perspective that investing in yourself is part of building a different future

This is about making a decision from clarity, not exhaustion.

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.

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 life
• Permission to stop over-explaining your desire to leave
• Clarity that your impact does not end when you leave the classroom
• Confidence that choosing yourself is not selfish
• A shift in how you view your career and your options

You 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 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.