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 more even when they have earned it.

This episode is not about dating tips or career hacks. It is about self-trust, preparation, and building the courage to ask for what you actually want instead of accepting what shows up.

When you listen to this episode, you’ll walk away with:

• A clearer understanding of how your dating patterns and career patterns mirror each other
• Permission to stop settling just because something feels familiar or safe
• A new way to think about preparation instead of perfection
• Language to ask for more without guilt or over-explaining
• A reminder that discomfort is not a red flag. It is often the doorway
• Validation that wanting more does not make you ungrateful or unrealistic

You are allowed to want a career and relationships that meet you where you are now. This episode will help you start acting like it.

• 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'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 expected.

We talk about timelines, persistence, fear, and the pressure teachers quietly carry when their exit plan doesn’t go as fast as they hoped. This episode is about learning how to keep moving without turning delays into self-doubt.

When you listen to this episode, you’ll walk away with:

• Relief that you are not behind or broken
• Clarity around why timelines often create more pressure than progress
• Permission to stop making delays mean failure
• A grounded way to think about investing in yourself without guilt
• A reminder that belief and emotional regulation matter as much as strategy
• A stronger connection to your why when motivation feels shaky

Your transition is not late. It’s unfolding. This episode will help you stay steady while it does.

• 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'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 education, how she reframed her experience, and the internal shifts required to show up confidently in a completely new world.

This conversation is honest about the work. The mindset shifts. The patience. And the strategy it takes to move from teaching into corporate without losing yourself along the way.

When you listen to this episode, you’ll walk away with:

• Belief that teachers really do belong in corporate roles
• Clarity on why strategy matters more than motivation
• A grounded understanding of how confidence shows up in interviews
• Permission to stop underselling your experience
• A realistic picture of what the job search process requires
• Reassurance that taking your time does not mean you are behind
• Validation that your skills translate, even if the language is different
• A calmer, more intentional way to think about your next move

This is not about rushing your exit. It is about making a smart 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)

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 realize how much you were carrying for so long.

We talk about the PTSD many teachers don’t realize they’re operating with. We talk about learning how to feel safe at work again. We talk about time freedom, quiet calendars, and the discomfort that comes with peace when you’ve been in survival mode for years.

This episode is about normalizing what you feel after the transition and helping you stop questioning whether you made the right decision.

When you listen to this episode, you’ll walk away with:

• Relief that what you’re feeling is normal
• Permission to slow down and rebuild your sense of safety
• A clearer understanding of how corporate work actually operates
• Confidence navigating politics without losing yourself
• Awareness of how to document your value without overworking
• Reassurance that your teacher skills absolutely transfer
• A deeper trust that you are already successful

This episode will help you settle into the freedom you worked so hard to create.

• 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'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, review your portfolio, and sit across from you in an interview.

We unpack how many teachers unintentionally block their own success by over explaining their classroom experience instead of positioning their transferable skills in a way EdTech understands.

When you listen to this episode, you’ll walk away with:

• A clear understanding of what EdTech hiring managers are actually evaluating when they interview transitioning teachers.
• Confidence in how to position your teaching experience as relevant, hireable skills instead of over explaining your classroom background.
• Clarity on what you still need to learn or prove so you can stop guessing and start showing up as a strong EdTech candidate.

This episode is not about motivation. It is about clarity. And clarity changes everything.

• 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’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:

• A shift in how you think about failure and what it really means
• A sense of relief knowing you’re not “behind” or broken
• Permission to stop waiting for confidence before you move
• A deeper trust in yourself to figure things out as you go
• The feeling of being grounded, steadied, and ready to keep going

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.

• 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’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:

• A clearer sense of what really determines success in a career transition
• A mindset shift that helps you stop waiting for certainty and start moving
• A stronger sense of personal responsibility and ownership over your next move
• More confidence navigating uncertainty without spiraling
• A renewed commitment to treating your transition as non-negotiable

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.

• 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’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

• 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 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 corporate (and why neither path is as “safe” as teachers think).
• Why transitioning educators are more employable than they realize when they learn how to articulate their value.
• How to build six-figure skills that make you career-proof, layoff-proof, and recession-proof.
• The mindset shift that instantly reduces fear around job stability and replaces it with strategy.
• How to think about promotions, growth, and advancement from Day 1 in your corporate role.
• The power of continuous learning, reinvention, and believing in your ability to pivot at any time.

This episode will help you stop waiting for job safety to be “given” to you — and instead learn how to create it for yourself.

• 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, 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:

• Why interviews don’t automatically turn into offers
• The mindset gap most transitioning teachers don’t even realize they have
• The real reason so many educators feel “stuck” even when they’re applying
• Why confidence, identity, and self-belief matter just as much as your resume
• Why setbacks don’t mean you’re unqualified — they mean you need a new strategy

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.

• 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)