063: The Top 10 Reasons Teacher Career Transitions FAIL and How to Succeed in 2026
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063: The Top 10 Reasons Teacher Career Transitions FAIL and How to Succeed in 2026

1:03:11 Jan 9, 2026
About this episode
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.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)
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