Pretty Rich Teacher

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...

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...

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...

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 t...

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 sh...

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 betw...

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...

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 ex...

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 o...

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 Custom...

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 whi...

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 fut...

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 choos...

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. Y...

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 wit...

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 g...

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 m...

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...

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...

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...

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...

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 mor...

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 exp...

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 e...

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...