067: What to Do If Your Career Transition Is Taking Longer Than Planned
Fri Feb 06 2026
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 brokenClarity around why timelines often create more pressure than progressPermission to stop making delays mean failureA grounded way to think about investing in yourself without guiltA reminder that belief and emotional regulation matter as much as strategyA 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)
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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 brokenClarity around why timelines often create more pressure than progressPermission to stop making delays mean failureA grounded way to think about investing in yourself without guiltA reminder that belief and emotional regulation matter as much as strategyA 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)