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 conversation about disappointment, shame, resilience, and choosing to keep going anyway.
When you listen to this episode, you’ll walk away with:
If you’re ready to stop making fear the decision-maker—and start moving forward even when it’s uncomfortable—this episode will meet you right where you are.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 corporate. This episode is about taking ownership, getting honest, and deciding that your next career move is not optional.
When You Listen to This Episode, You’ll Walk Away With:
There is nothing wrong with you for wanting more. But wanting more isn’t enough.
When you’re ready to stop hoping it works out—and start moving like it will—this episode will meet you exactly where you are.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 knowledge so interviews stop feeling intimidating
✨ The difference between wanting out and having an actual exit plan
✨ How understanding career paths changes your resume and your confidence
✨ Why burnout must be addressed before you transition—not after
✨ How your teaching skills translate into corporate value (even if it doesn’t feel obvious yet)
✨ What “doing the work” really looks like during a career pivot
✨ Why clarity beats speed—and how to get both
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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:
This episode will help you stop waiting for job safety to be “given” to you — and instead learn how to create it for yourself.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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,” the mindset shifts that actually lead to job offers, and the exact mistakes that keep educators stuck in the classroom longer than they planned.
In this episode you will learn:
If you’re a teacher who knows you’re meant for more, this episode will help you think differently, prepare differently, and show up as the version of you who actually gets the job.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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:
This is a story that will make you feel capable, prepared, and ready to take your next step with confidence.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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, and more career options.
If you’ve ever felt stuck, burnt out, or guilty for wanting more than teaching, this episode gives you both the language and the liberation.
You will learn:
✨ The emotional and financial cost of being a “P.O.U.R Teacher”
✨ How burnout leads to desperate job decisions
✨ The identity shift every Rich Teacher must make
✨ How to rewire your thoughts about money, success, and worth
✨ The mindset required to build a six-figure career beyond the classroom
This episode is your permission slip to stop shrinking and start receiving.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 actual job offers, not “great conversations.”
In this episode, you’ll walk away with:
If you enjoyed this episode, you’ll love:
✨ Episode 55: “Rejection Sensitivity”
✨ Episode 45: “How to Choose Freedom Over Fear”
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 when you listen:
Whether you’re applying for EdTech, corporate learning, or customer success roles, this episode will help you regulate your emotions, track your progress with confidence, and reframe every rejection as proof that you’re still in the game.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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:
After listening to this episode, you’ll finally understand why waiting for “next year” only keeps you stuck — and how to choose courage, clarity, and freedom this year instead.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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:
After listening to this episode, you’ll finally stop dreading Sundays — and start believing that peace is possible, even before Monday begins.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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.
✨ You’ll learn:
After listening to this episode you will also walk away knowing that freedom isn’t selfish. It’s the most powerful act of self-trust you can make!
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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:
After listenting you will learn that fear isn’t the enemy — it’s your invitation to grow.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 "impossible to land a job in".
You’ll learn how to:
I also walk you through how the Six-Figure Educator Certification + Mentorship gives you the roadmap to put these skills into action, so you can land your dream EdTech Customer Success, or Sales role without guessing what to do next.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 career coach even after I thought I could do it all myself — and how that single decision changed everything about how I show up, sell my skills, and get paid what I’m worth.
You’ll learn how to:
This episode is for the high achiever who’s tired of playing small, overthinking every move, and wondering why “hard work” still isn’t translating into job offers. Sometimes, the smartest move isn’t working harder — it’s hiring help.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 and being a career seeker, and why mastering that difference could be the exact thing that helps you land a six-figure offer faster.
You’ll learn how to:
By the end, you’ll know exactly how to use LinkedIn as your six-figure launchpad, not your diary.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 between DIY, resume writers, and career coaches, and how to know which one fits your stage of transition.
You’ll learn how to:
Plus, I share what’s worked for me and my clients — including how investing strategically in your career transition can literally be the move that gets you paid more, faster.
This isn’t just about resumes or coaching — it’s about building a plan that gets you interviews, confidence, and clarity.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 even when the path gets messy, focusing on skills over timelines is what collapses the gap between where you are and where you want to be.
✨ Here's what you'll walk away with when you listen:
Whether you've been teaching 2 years or 20, Ashley's story will show you that it's never too late—even if you've already tried once.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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:
If you've been applying but not landing interviews—or you're afraid you'll be stuck in education forever—this episode will show you exactly what needs to shift.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)
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 to believing she was stronger than her fears.
✨ Here’s what you’ll walk away with when you listen:
Funké’s journey is more than a career change, it’s a reminder that your strength grows every time you choose to show up, even when it’s uncomfortable.
Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)