Pretty Rich Teacher

If you're a teacher who keeps hearing that EdTech is a “natural next step” but you are not getting interviews or offers, this episode is for you. In this episode, I break down what EdTech hiring managers are actually looking for when they hire transitioning teachers. Not what we assume they want. Not what career coaches vaguely suggest. What they are truly screening for when they read your resume,...

If you’re a teacher who’s terrified of failing after leaving the classroom—or secretly worried that trying and not succeeding would be worse than staying—this episode is for you. In this episode, I’m talking honestly about failure what it actually looks like during a teacher career transition, why it’s unavoidable, and why avoiding failure is the fastest way to stay stuck. This is a real conversat...

If you’re a teacher who knows you want out of the classroom but feels stuck in uncertainty, fear, or overthinking—this episode is for you. If you keep saying “I want to leave” but haven’t fully committed to the process yet, you need this conversation. In this episode of the Pretty Rich Teacher Podcast, I’m breaking down the five non-negotiable ways to guarantee a successful transition into corpora...

If you’re a teacher who knows you can’t keep doing this but you also don’t know where to start this episode is for you. In this episode of The Pretty Rich Teacher Podcast, I break down exactly how to create a realistic, strategic exit plan into corporate in less than 30 days—without panic-applying, guessing, or starting another degree. In This Episode, You’ll Learn: ✨ How to build corporate knowl...

In this episode of the Pretty Rich Teacher Podcast, we’re getting real about corporate layoffs, job safety, and the government shutdown — and what all of this actually means for transitioning teachers. If you’ve been scared to leave teaching because you think corporate isn’t “stable,” this is the episode you needed yesterday. You’ll walk away with: The truth about layoffs in BOTH education and cor...

In this episode of the Pretty Rich Teacher podcast, Jazmyne Dionne breaks down one of the biggest misunderstandings educators have when they’re transitioning into corporate or EdTech roles: interviews and job offers are NOT the same thing — and they require two completely different skill sets. Inside this episode, Jazmyne explains the real difference between “interview ready” and “offer ready,” th...

In this week's episode, I’m sharing how Jada became a standout EdTech CSM candidate with only four years of teaching experience. Her story is a reminder that when you know how to package your experience, you become undeniable. Her approach made her confident, clear, and prepared in ways most transitioning teachers never are. When you listen to this episode, you’ll walk away with: The mindset shift...

In this episode, Jazmyne breaks down the REAL mindset keeping teachers underpaid, overlooked, and overwhelmed — and introduces P.O.U.R , the framework behind the P.o.u.r. Teacher Mindset . You’ll learn how these four patterns silently drain teachers financially, emotionally, and professionally — and how to step into the Rich Teacher Mindset , the identity that unlocks more money, more confidence,...

If you’ve ever walked out of an interview feeling hopeful… only to hear nothing for days, weeks, or forever? This episode is going to change how you see your entire job search. Today we’re talking about “ghosting” — what it actually is, why it feels so personal for educators, and how to shift out of discouragement and into strategy, self-awareness, and emotional regulation so you can start getting...

In this episode, Jazmyne gets real about rejection sensitivity especially for high-achieving women navigating their career transition. If you’ve ever felt that familiar gut punch after a “thank-you-for-applying” email, this one’s for you. Jazmyne unpacks why rejection hits harder for those used to excelling, and how to turn those moments into data, direction, and deeper belief. What You’ll Learn w...

In this episode, Jazmyne exposes the hard truth behind the phrase every burned-out teacher says: “I’ll just stay one more year.” She breaks down why staying stuck only deepens exhaustion, delays growth, and costs you opportunities — both emotional and financial. ✨ You’ll learn: Why staying “one more year” makes burnout worse, not better How to stop future-faking your happiness and start taking re...

In this episode, Jazmyne dives into one of the most common — and painful — experiences teachers face: the Sunday Scaries . She unpacks what’s really happening beneath the anxiety, exhaustion, and dread that hit before a new week, and shares how to begin healing it for good. ✨ You’ll learn: What the Sunday Scaries actually are and why they hit so hard How to journal through your Sunday thoughts to...

In this episode, Jazmyne speaks directly to veteran teachers who feel torn between loyalty and liberation. She opens up about her own journey, the burnout cycle that keeps seasoned educators stuck, and what it really means to choose freedom over fear. You’ll also learn her powerful H.E.A.L. framework to help you release guilt, rebuild identity, and rediscover who you are beyond the classroom. ✨ Y...

In this episode, Jazmyne breaks down why leaving teaching feels so scary — even when you know it’s time. She dives into the fears of starting over, financial uncertainty, and the emotional guilt that keeps teachers stuck, showing you how to reframe fear as growth and build trust in your next chapter. ✨ You’ll learn: What fear is really trying to tell you How to release guilt about leaving your st...

In this episode of the Pretty Rich Teacher podcast, I’m revealing the five core skills that helped me — and my clients — land interviews and offers fast. If you’ve been stuck waiting for your “big break,” this is your wake-up call. Career transitions aren’t about luck — they’re about skills. And when you master these five, you’ll stand out instantly in the same job market that people claim to be "...

In this episode of the Pretty Rich Teacher podcast, I’m getting real about something I don’t think enough educators talk about — the moment I realized I couldn’t DIY my career transition anymore. If you’ve been grinding on applications, rewriting your resume 15 times, or feeling like “maybe it’s just not my time yet,” this one’s for you. I’m pulling back the curtain on why I decided to hire a care...

In this episode of the Pretty Rich Teacher podcast, we’re talking about one of the biggest mistakes I see teachers make when trying to pivot into EdTech or corporate... If you’ve been posting your job search struggles, over-sharing about burnout, or thinking you HAVE to post on LinkedIn every week to get hired, this episode is for you. I’m breaking down the difference between being an influencer a...

I’m breaking down one of the biggest questions teachers ask when they’re ready to leave the classroom — “Should I hire a resume writer, work with a career coach, or just figure it out myself?” If you’ve been stuck updating your resume for weeks, scrolling job boards at midnight, or wondering what’s actually worth investing in — this episode is for you. I walk you through the real difference betwee...

In this episode, Jazmyne sits down with her client Ashley, who shares her journey of transitioning from a 16-year career in education to landing her dream EdTech sales role. Ashley opens up about ending her contract without a job lined up and the moment she stopped obsessing over her timeline and started building the skills that would make her irresistible to hiring managers. Her story proves that...

In this episode, Jazmyne discusses the importance of shifting into a victory mindset, particularly for women in education seeking to transition into six-figure careers. She introduces a powerful framework that reveals three roles we unconsciously play that keep us stuck—and how recognizing these patterns is the key to breaking free. ✨ Here's what you'll walk away with when you listen: A transform...

In this week’s episode Funké shares how resilience, mentorship, and self-belief helped her navigate the messy middle of her career transition and step into a whole new chapter of life. As a veteran teacher, she could have told herself it was too late. She could have let interview fears and self-doubt keep her stuck. But instead, she chose to stay open—open to therapy, open to mentorship, and open...

What does it actually mean to be classroom optional—and how do you get there for good? In this episode Jazmyne unpacks the two real reasons educators go back to the classroom after landing a corporate role: because they want to, or because they feel they have no other choice. While both are valid, Jazmyne reveals why the true goal is freedom—and that comes from being classroom optional. By the end...

In this episode, Dr. Jazmyne sits down with Jasmine, a young teacher who chose to pivot after just two years in the classroom. Together, they explore what it means to walk away from teaching early in your career, how to navigate the fear of the unknown, and why mindset is the foundation for any big life change. Jasmine shares her journey of embracing discomfort, reframing negative thoughts through...

In this episode of the Pretty Rich Teacher podcast, Dr. Jazmyne Dionne opens up about something so many high-achieving women feel but rarely say out loud: timeline heartbreak. If you’ve ever whispered to yourself, “I should be further along by now,” this episode is for you. If you’ve circled birthdays, school years, or New Year’s deadlines on your calendar and felt crushed when life didn’t match t...

If you’ve ever thought about leaving the classroom, chances are this question has kept you up at night: “What happens to my retirement if I walk away?” You’re not alone—this is one of the most common (and confusing) fears teachers have when they’re ready to transition. And in this episode of the Pretty Rich Teacher podcast, I’m sitting down with my money coach, Aqura Nicholson, to break it all dow...