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Becoming a principal wasn't on my radar when I was happily teaching math and coaching sports. Someone else spotted my leadership potential before I did—a pivotal moment that set me on an unexpected path to school administration.
My journey from classroom teacher to high school principal wasn't straightforward or easy. It required multiple graduate degrees, mentorship from experienced administrators, and a combined total of 25 interview attempts before landing my dream role. Through each rejection, I refined my approach and learned valuable lessons about educational leadership that I'm passionate about sharing with aspiring administrators.
This deeply personal episode pulls back the curtain on the challenges of transitioning into school leadership. I detail how my perspective on principalship transformed when I witnessed a leader who showed up in classrooms to support rather than criticize. I explain how participation in leadership academies and deliberate resume-building experiences prepared me for administrative roles, even when the path wasn't clear.
The turning point came when a superintendent told me I was "interviewing for the wrong job" because I answered questions like a principal, not an assistant principal. This revelation changed my entire approach to job searching and helped me recognize where my leadership style truly belonged.
For those considering educational leadership, I offer eleven practical strategies developed through my experiences—from wearing school colors to interviews to creating comprehensive transition plans that demonstrate your vision. Most importantly, I emphasize authenticity throughout the process, as school communities are searching for leaders who align with their values and culture.
Whether you're contemplating your first leadership position or looking to advance in educational administration, this episode provides honest insights into finding your place as a school leader. The journey may not be easy, but for those called to make a broader impact in education, it's immensely rewarding.
60-90-30 Transition Plan:
Connect with Principal JL Click Here:
Teach Better Mid Roll Network Ad
Support the show
Click Here to Connect with Principal JL:
By Jeff Linden5
4343 ratings
Send us a text
Becoming a principal wasn't on my radar when I was happily teaching math and coaching sports. Someone else spotted my leadership potential before I did—a pivotal moment that set me on an unexpected path to school administration.
My journey from classroom teacher to high school principal wasn't straightforward or easy. It required multiple graduate degrees, mentorship from experienced administrators, and a combined total of 25 interview attempts before landing my dream role. Through each rejection, I refined my approach and learned valuable lessons about educational leadership that I'm passionate about sharing with aspiring administrators.
This deeply personal episode pulls back the curtain on the challenges of transitioning into school leadership. I detail how my perspective on principalship transformed when I witnessed a leader who showed up in classrooms to support rather than criticize. I explain how participation in leadership academies and deliberate resume-building experiences prepared me for administrative roles, even when the path wasn't clear.
The turning point came when a superintendent told me I was "interviewing for the wrong job" because I answered questions like a principal, not an assistant principal. This revelation changed my entire approach to job searching and helped me recognize where my leadership style truly belonged.
For those considering educational leadership, I offer eleven practical strategies developed through my experiences—from wearing school colors to interviews to creating comprehensive transition plans that demonstrate your vision. Most importantly, I emphasize authenticity throughout the process, as school communities are searching for leaders who align with their values and culture.
Whether you're contemplating your first leadership position or looking to advance in educational administration, this episode provides honest insights into finding your place as a school leader. The journey may not be easy, but for those called to make a broader impact in education, it's immensely rewarding.
60-90-30 Transition Plan:
Connect with Principal JL Click Here:
Teach Better Mid Roll Network Ad
Support the show
Click Here to Connect with Principal JL:

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