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Episodes & Guests

Season 1

Where it all began — the first season of honest conversations on life in and beyond the classroom.

Samantha Stanley
Episodes 1 & 2

Samantha Stanley

Elementary educator turned EdTech

A seasoned elementary educator with 25 years in the classroom, Samantha moved into EdTech curriculum sales — then found the best of both worlds, returning to teach while keeping her ed-tech role. She shares how to translate classroom skills and exit professionally.

Jessica Grant
Episode 3 · 52 min

Jessica Grant

Music teacher to administrator

A music teacher, clinician, and podcast creator, Jessica shares her candid journey from the music classroom into school administration — and what leadership looks like from the other side of the desk.

Kendal Askins
Episodes 4, 7 & 13

Kendal Askins

Teacher to principal, director & CEO

Kendal began teaching math and STEAM before becoming a principal, then a district director, and ultimately a CEO. Across a three-part arc she shares how she kept climbing — now leading an Allentown School District partnership at the Da Vinci Science Center, running a tutoring company, and speaking nationally.

Oslyn Rodriguez
Episode 5

Oslyn Rodriguez

Teacher to homeschool founder

Oslyn left the classroom to found her own homeschool, building a learning environment on her own terms and helping families reimagine what education can look like.

Erin Mote
Episode 6

Erin Mote

Charter school co-founder & CEO

Erin co-founded a charter school and grew into the CEO seat, sharing what it takes to build and lead an education organization from the ground up.

Cherise Irons
Episodes 8 & 9

Cherise Irons

Teacher to school administrator

Over a two-part conversation, Cherise shares her move from the classroom into school administration — the mindset, preparation, and leadership lessons behind the step up.

Andy Rettke
Episode 10

Andy Rettke

Wrestling coach to contractor

Andy traded the wrestling mat for the job site, moving from coaching into running his own work as a general contractor — proof that an educator’s skills travel far beyond school.

Latisha Elliott
Episode 11

Latisha Elliott

Teacher’s assistant to administrator

Latisha rose from teacher’s assistant to administrator, sharing how she grew within the system and stepped confidently into leadership.

Rick Magnani
Episode 12 · 37 min

Rick Magnani

Music teacher, joyfully retired

After 26+ years as a celebrated music teacher — and a mentor to host Alex Kirton — Rick shares a heartfelt look at closing the classroom chapter and living retirement with joy and purpose.

Dr. Deborah Wortham
Episode 14 · 53 min

Dr. Deborah Wortham

Teacher to superintendent

From a determined student in Chicago to a transformative superintendent, Dr. Wortham shares a powerful story of belief, resilience, and intentional leadership in education.

Kathy Kuddes
Episode 15 · 61 min

Kathy Kuddes

Music teacher to fine arts director

Kathy moved from the music classroom to Director of Fine Arts and on to the international stage as a presenter, sharing how curiosity and leadership opened each new door.

Gordon Gooding
Episode 16 · 63 min

Gordon Gooding

Social worker & wellness founder

A school social worker who founded his own wellness group, Gordon talks educator burnout, mental health, and building support systems that help teachers and students thrive.

Jeff Patterson
Episode 17 · 62 min

Jeff Patterson

CEO of Gaggle

CEO of Gaggle, Jeff explores the evolution of EdTech and student safety — balancing technology with human judgment and prioritizing mental-health support in schools.

Jeff Bradbury
Episode 18

Jeff Bradbury

Author, speaker & tech coach

A teacher who became an author, national speaker, and technology coach, Jeff shares how educators can extend their impact beyond the classroom through writing, speaking, and EdTech.

Keyla Kirton
Episodes 19 & 20

Keyla Kirton

HR leader, consultant & ERP CEO

From journalism and producing for 60 Minutes to higher-ed leadership, HR operations in large school systems, and now consulting and tech as an ERP CEO — Keyla’s path shows how to pivot with purpose. A two-part special edition.

Teachers Transitions Podcast  ·  Alexander Kirton  ·  alex@teacherstransitions.com  ·  631-357-4905