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In this episode of the Transformative Principal podcast, host Mike Caldwell talks with Jason Leshowitz, a New Jersey arts administrator and founder of Rejection Proof Career, about his upcoming book The Rejection Proof Educator. Jason shares how educators and school leaders can translate their skills and experience into compelling resumes and interview answers, whether they're pivoting upward into leadership or transitioning into education-adjacent careers like ed tech and instructional design. The conversation covers reframing your professional story, building relevant experience before an opportunity arrives, using LinkedIn (and Facebook) to network effectively, and practical strategies for standing out in a competitive job market.
Show Notes:
Website: rejectionproofcareer.com
LinkedIn: linkedin.com/in/jason-leshowitz
Instagram: @rejectionproofcareer
Book: The Rejection-Proof Educator: Translating Your Experience into Better Pay and Bigger Opportunities (coming soon)
We’re proud to be sponsored by IXL.
IXL’s comprehensive teaching and learning platform for math, language arts, science, and social studies is accelerating achievement in 95 of the top 100 U.S. school districts. Loved by teachers and backed by independent research from Johns Hopkins University, IXL can help you do the following and more:
🚀 Ready to see why leading districts trust IXL for their educational needs? Visit IXL.com/BE today to learn more about how IXL can elevate your school or district.
By Jethro Jones4.6
102102 ratings
In this episode of the Transformative Principal podcast, host Mike Caldwell talks with Jason Leshowitz, a New Jersey arts administrator and founder of Rejection Proof Career, about his upcoming book The Rejection Proof Educator. Jason shares how educators and school leaders can translate their skills and experience into compelling resumes and interview answers, whether they're pivoting upward into leadership or transitioning into education-adjacent careers like ed tech and instructional design. The conversation covers reframing your professional story, building relevant experience before an opportunity arrives, using LinkedIn (and Facebook) to network effectively, and practical strategies for standing out in a competitive job market.
Show Notes:
Website: rejectionproofcareer.com
LinkedIn: linkedin.com/in/jason-leshowitz
Instagram: @rejectionproofcareer
Book: The Rejection-Proof Educator: Translating Your Experience into Better Pay and Bigger Opportunities (coming soon)
We’re proud to be sponsored by IXL.
IXL’s comprehensive teaching and learning platform for math, language arts, science, and social studies is accelerating achievement in 95 of the top 100 U.S. school districts. Loved by teachers and backed by independent research from Johns Hopkins University, IXL can help you do the following and more:
🚀 Ready to see why leading districts trust IXL for their educational needs? Visit IXL.com/BE today to learn more about how IXL can elevate your school or district.

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