Rejection Proof Career with Jason Leshowitz

Rejection Proof Career with Jason Leshowitz

July 5, 2026 · 34 min · Season 13 · Episode 716

About this episode

Jason Leshowitz discusses strategies for educators to enhance their career prospects and effectively transition into new roles.

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…

People in this episode

Host: Mike Caldwell

Guest: Jason Leshowitz

Topics covered

Keywords

Sponsors

IXL

Mentioned in this episode

Organizations: Rejection Proof Career, Johns Hopkins University

Books & works: The Rejection-Proof Educator

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