Pretty Rich Teacher
Pretty Rich Teacher
Dr. Jazmyne Dionne
063: The Top 10 Reasons Teacher Career Transitions FAIL and How to Succeed in 2026
1 hour 3 minutes Posted Jan 9, 2026 at 5:00 am.
mentorship into a six figure edtech career? Book a free sales call here to get started.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.
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Show notes
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 meansA sense of relief knowing you’re not “behind” or brokenPermission to stop waiting for confidence before you moveA deeper trust in yourself to figure things out as you goThe feeling of being grounded, steadied, and ready to keep goingIf 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.Are you a burnt out women in education ready for direct coaching that actually gets you hired into an 100k EdTech Career in less than 90 days? Ready for 1:1 mentorship into a six figure edtech career? Book a free sales call here to get started.Want to find out what’s blocking you from making 100k outside the classroom? Take the free quiz here and find out. You will then get access to a free personalized training to help you take action on your next step.Make sure to follow @prettyrichteacher on IG +TikTok and Linkedin (I go live weekly on Tuesdays!) + Youtube (Weekly Video Podcasts + Transitioned Teacher Vlogs) click here to access podcast listening guide.