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:

• Recognize when doing it alone is keeping you stuck in circles
• Shift from “I can figure it out” to “I deserve expert support”
• Understand what career coaches actually do — and how to spot the real ones from the scams
• Market your transferable skills like a pro, even if you’ve never worked outside of education
• Reframe investing in a coach as the smartest (and fastest) way to make more money

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.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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:

• Position yourself as a career-ready professional — not a teacher trying to escape the classroom
• Shift your mindset from “posting for validation” to “showing up for opportunities”
• Craft a LinkedIn profile that actually attracts recruiters (and makes them message you)
• Network intentionally and build genuine relationships with hiring managers
• Avoid the rookie mistakes that silently disqualify amazing educators every day

By the end, you’ll know exactly how to use LinkedIn as your six-figure launchpad, not your diary.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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:

• Define what you actually want in your next role (before you waste time applying to everything)
• Understand the job market and why EdTech and corporate roles are ideal for former educators
• Master the mindset needed to make a real career pivot — not just another job search
• Spot the difference between polished documents and a real job strategy
• Decide when it’s time to stop guessing and start getting professional guidance

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.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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:

• Why letting go of your timeline is the breakthrough you need
• The power of lifetime access and coaching support in landing your offer
• Networking and interviewing strategies that work for educators
• What to do when you hear "no" and why it doesn't mean stop
• How to become the role before you land it

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.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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:

• A transformational framework that reveals exactly how you're showing up in your transition
• Why "waiting for the right opportunity" is actually keeping you comfortable (not ready)
• How to step into a victory mindset through self-observation and awareness
• The power of radical ownership in accelerating your career transition
• Why embracing your power and privilege is the secret to your six-figure journey

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.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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:

• Why showing up for yourself matters more than being “perfect”
• How resilience and therapy can move you through seasons of doubt
• Why mentorship is a shortcut to confidence and clarity
• How self-worth shifts everything about the way you interview and apply
• Proof that it’s never too late to rewrite your story

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.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)

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 of this episode, you’ll know exactly how to:

• Reframe the classroom as a choice rather than a fallback plan
• Build the skills that give you long-term security in corporate spaces
• Leverage your teaching experience as a superpower in interviews and roles
• Create career options beyond education so you’ll never feel trapped again

✨ This isn’t just about leaving teaching it’s about stepping into a life where you’ll always have options, and teaching is one of them, not your only one.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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, 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 thought scripts, and learning to see feedback as a gift instead of criticism. She opens up about the duality of independence — how you can be strong and self-sufficient while also receiving help — and why gratitude has been key in softening the pressures of building a new career.

By the end of this conversation, you’ll walk away with:

• A new perspective on fear and how to use it as fuel for growth
• Thought scripts to reframe negative beliefs and boost confidence
• A mindset shift that positions sales as an extension of teaching and connection
• A reminder that asking for help is strength, not weakness
• A practical way to use feedback and gratitude to accelerate personal growth

This episode is a must-listen for any teacher — whether you’re two years in or twenty — who’s ready to explore what’s possible beyond the classroom!

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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, 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 the plan — this episode is for you. If you’ve ever scrolled past someone else’s success and thought, “Why not me, yet?” this episode is for you.

Jazmyne shares her own stories of chasing deadlines that didn’t pan out and the heartbreak that comes with it. But she also gives you the reframes you need:

• Why missing your “timeline” isn’t failure — it’s redirection.
• How to focus on building skills, not just chasing dates.
• Simple mindset shifts that will help you breathe easier when the clock doesn’t match your calling.
• Permission to stop hustling for someone else’s version of “on time” and start owning your own pace.

Press play and let this conversation remind you: you are not behind. You’re right on time.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

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 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 down.

Whether you’re just a few years in or you’ve been teaching for over a decade, you’ll finally get straight answers to questions like:

• Do I lose my retirement if I leave teaching early?
• What does it really mean to be vested?
• How many years do I need before I keep my retirement benefits?
• Can I roll my teacher retirement account into something else?
• How do I make sure I don’t leave money on the table?

💡 In this conversation, you’ll learn:

• ✔️ The truth about vesting and eligibility (hint: it’s not “30 years or nothing”).
• ✔️ Step-by-step options for reviewing your retirement account.
• ✔️ What a rollover looks like and why it might benefit you.
• ✔️ How to make smart, confident financial decisions when leaving education.

And I’ll share exactly what I did with my teacher retirement when I left the classroom, so you can see what’s possible for you, too.

By the end of this episode, you’ll walk away with clarity, confidence, and a plan to protect your money—so you can build the career (and life) you actually want.

• Want free weekly exclusive free tips + trainings ? (that I do not share anywhere else) ➡️ Join the Pretty Rich Weekly Email list!
• Ready to create your exit plan into corporate in less than 30 days? ➡️ Enroll in the Exit Plan Course for Transitioning Teachers for exclusive bonuses including a free resume review!
• Are you a woman in education ready for mentorship into a six-figure EdTech career in less than 6 months? ➡️ book your free 1:1 mentorship sales call. Together, we’ll create a plan to help you make an extra $10K–$40K every year in a new career and learn the skills required to become classroom optional for good!

Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs)