063: The Top 10 Reasons Teacher Career Transitions FAIL and How to Succeed in 2026
Pretty Rich Teacher · Jazmyne Dionne
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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 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.
Are you a burnt out women in education looking to leave the classroom but don't know where to start? Register for my Free Training: How to Leave the Classroom by August and Land a Six Figure EdTech Job in 90 Days - May 7th at 6:15PM EST
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