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PODCAST

The Pit Pony Podcast - Life After Teaching

Sharon Cawley and Sarah Dunwood

Sharon Cawley and Sarah Dunwood talk to former teachers about exiting from the classroom and thriving.Don"t forget to leave us a VOICEMAIL, quickly and easily at https://www.speakpipe.com/pitponypodcastSupport the podcast by buying us a coffee here:https://buymeacoffee.com/thepitponyclub

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All Episodes

70:40

039 - Pit Pony Grant Decker - Classroom to Record...

The Pit Pony Podcast - Life After Teaching ·

2025/03/18

This week on The Pit Pony Podcast, we sit down with the incredible Grant Decker – a former teacher whose love for music led him to open his own record shop. After years in the classroom, supporting students with complex needs, Grant realised it was time for a change. In this episode, he shares his inspiring journey from education to entrepreneurship, the challenges of balancing work and family, and how he built a thriving business from his passion for vinyl. Thinking about your own exit strat...

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85:29

038 - Pit Pony Paul Lennon - Classroom to NHS Health...

The Pit Pony Podcast - Life After Teaching ·

2025/03/11

In this episode of the Pit Pony Podcast, we sit down with Paul Lennon, a former teacher with 28 years of experience in secondary schools across the UK and around the world. Paul started his career as a PE teacher, eventually working his way up to head of department, assistant principal, and IB Diploma Coordinator. But his journey took an unexpected and deeply challenging turn when he found himself in a toxic school environment that left him battling anxiety, self-doubt, and ultimately a panic...

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63:33

036 - Pit Pony Hollie Jones - Classroom to...

The Pit Pony Podcast - Life After Teaching ·

2025/03/04

In this powerful two-part episode, we sit down with Hollie Jones, a former teacher turned neurodiversity practitioner, whose journey out of the classroom is one of resilience, advocacy, and hard-won justice. Hollie always believed teaching was her lifelong career - until she faced systemic barriers, discrimination, and a lack of understanding about neurodivergent needs in the workplace. What started as a request for simple, reasonable adjustments quickly spiralled into a legal battle for her ...

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94:22

037 - Pit Pony Hollie Jones - Classroom to...

The Pit Pony Podcast - Life After Teaching ·

2025/03/04

In this second part to Hollie Jones’ story, we dive deeper into her legal battle for workplace justice, the emotional toll of discrimination, and the life-changing shift that followed. After an appalling "well-being" call that questioned her ADHD diagnosis, Hollie knew she was facing more than ignorance - she was up against systemic failure. With unwavering determination, she documented every step, stood her ground, and ultimately forced those in power to reckon with their treatment of ...

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62:46

035 - Pit Pony Ruth O'Neill - Classroom to SEND...

The Pit Pony Podcast - Life After Teaching ·

2025/02/25

In today's episode of The Pit Pony Podcast, we sit down with Ruth O’Neill, an educator who spent over 20 years in the classroom before stepping into a new role as a SEND consultant and English tutor. Ruth’s journey took her from teaching in the UK to classrooms in Cairo and Costa Rica, before returning home to take on a challenging SENCO role. Over time, the pressures of the role, increasing workload, and systemic challenges pushed her to breaking point. Ruth opens up about the realities of w...

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71:03

034 - Pit Pony Sarah Cowen - Classroom to Head of...

The Pit Pony Podcast - Life After Teaching ·

2025/02/18

This week’s episode is a powerful one. We sit down with Sarah Cowen, a former drama teacher who never planned to teach—until she fell in love with the profession. But after 18 years, she faced the realisation that her boundaries, well-being, and identity had been eroded over time. Sarah’s story is one of deep reflection, empowerment, and transition. Now working as Head of Domestic Abuse Services, she shares: ✨ How she went from ‘accidental teacher’ to Mary Poppins of education, parachut...

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8:18

033 - Sliding Doors Stories - Part 5

The Pit Pony Podcast - Life After Teaching ·

2025/02/14

Welcome to another Sliding Doors Stories bonus episode, where we celebrate the incredible transformations our guests have experienced since leaving the classroom. In this episode, we hear from: ✨ Leanne Herring – from teacher to voice artist & content creator. ✨ Mark Thompson – from teacher to TV & film chaperone. ✨ Amy MacDonald – from teacher to forest school leader & content creator. Each of these stories is a powerful reminder that life after teaching can be filled with jo...

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66:20

032 - Pit Pony Katie Stone - Classroom to Virtual...

The Pit Pony Podcast - Life After Teaching ·

2025/02/11

Today, we sit down with Katie Stone, a former primary school teacher who left the classroom after facing work-related stress and the pressures of an informal support plan. Katie opens up about the emotional toll of teaching, the challenges of leaving, and how she found a new path that gave her both freedom and fulfilment. Now the owner of a successful virtual assistant agency, Katie shares how she turned her organisational skills, multitasking abilities, and work ethic - honed in teaching - i...

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7:02

031 - Sliding Doors Stories - Part 4

The Pit Pony Podcast - Life After Teaching ·

2025/02/07

We’re back with another special bonus episode of The Pit Pony Podcast - Sliding Doors Stories, Part 4! In this episode, we revisit those powerful moments when our guests reflect on the incredible experiences they’ve had since leaving the classroom. This week, we hear from: 🎨 Jane Lloyd – From classroom teacher to artist, embracing a life filled with creativity, fresh air, and even a pet sheep! 🧘 Gareth Isaacs – Now a mindfulness teacher, discovering the joy of truly living in the moment.

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68:05

030 - Pit Pony Amy MacDonald - From Classroom to...

The Pit Pony Podcast - Life After Teaching ·

2025/02/04

This week, we welcome Amy MacDonald, a former primary school teacher who transformed her love for teaching outdoors into a fulfilling new career. Amy’s journey is one of resilience, self-discovery, and inspiration, showing us that life after teaching can be rich with opportunities. In this episode, Amy shares: 🌿 Her journey through challenging school environments, including part-time battles and chronic unkindness. 🌟 How she found her passion for forest schools and outdoor learning. 💪 The

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19:37

029 - Sliding Doors Stories - Part 3

The Pit Pony Podcast - Life After Teaching ·

2025/01/31

We’re thrilled to bring you another Sliding Doors Stories bonus episode! This special collection features incredible moments from our guests that truly capture the magic of life after teaching.In this episode, we revisit the inspiring reflections of:✨ Rae Dillon – From classroom teacher to copywriter.Celebrating her dream wedding in Bora Bora - something teaching would never have allowed.✨ Hannah Jones – Former teacher turned Head of Prison Education.Sharing an emotional and deeply personal s...

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39:43

028 - Pit Pony Mark Thompson - Classroom to TV & Film...

The Pit Pony Podcast - Life After Teaching ·

2025/01/28

Mark Thompson is a former computing and business studies teacher with over 18 years of experience in education. After leaving the classroom in 2011, Mark transitioned into a unique and fulfilling career as a tutor and chaperone for children working on TV and film sets, including his work on CBBC. His role combines education with safeguarding, ensuring young actors meet their academic goals and thrive in a professional environment. Mark’s inspiring story highlights the power of ...

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6:13

027 - Sliding Doors Stories - Part 2

The Pit Pony Podcast - Life After Teaching ·

2025/01/24

We’re excited to share the second in our series of brand-new bonus episodes of the Pit Pony Podcast - a heartfelt collection of our guests’ incredible sliding doors moments. These powerful and inspiring stories celebrate the magic of life after teaching and the joy that comes from embracing new opportunities.In this episode, you'll hear from:✨ Rowena Hicks: From Classroom to AuthorRowena reflects on a transformative moment of self-worth and freedom, showing her the power of taking control and...

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41:53

026 - Pit Pony Leanne Herring - Classroom to Voice...

The Pit Pony Podcast - Life After Teaching ·

2025/01/21

In the second part of Leanne Herring’s inspiring story, we delve into her journey beyond the classroom and explore the incredible life she’s built since leaving teaching. From pursuing a master's degree in psycholinguistics to discovering her passion for voiceover artistry, Leanne shares how she turned creativity and resilience into a thriving career.Hear about the challenges she overcame, including financial worries and post-teaching anxieties, and how she embraced opportunities in content c...

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49:35

025 - Pit Pony Leanne Herring - Classroom to Voice...

The Pit Pony Podcast - Life After Teaching ·

2025/01/21

In the first part of this fantastic two-part episode, we introduce Leanne Herring, a passionate teacher whose love for education began as a six-year-old teaching her teddies. Spanning a decade-long teaching career across four schools, Leanne’s story unfolds with both moments of joy and deep challenges.Leanne reflects on her first school, where creativity flourished and she thrived, only to move to a second school where a toxic "mean girl" culture took its toll. From being excluded in staffroo...

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9:24

024 - Sliding Doors Stories - Part 1

The Pit Pony Podcast - Life After Teaching ·

2025/01/17

Sliding Doors Moments: From Chocolate to Celebrancy and Safari Dreams 🎙️Welcome to our first special bonus episode, where we celebrate the incredible "sliding doors" moments from our guests - those life-defining events that remind us why stepping out of the classroom can lead to extraordinary experiences.This week, we revisit the heartfelt stories of:🍫 Vicky Thurkettle, who shares how her leap from teaching to chocolatier gave her the gift of witnessing her daughter’s miraculous first

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68:42

023 - Pit Pony Lee Springett - Classroom to Barnardos...

The Pit Pony Podcast - Life After Teaching ·

2025/01/14

In todays episode of The Pit Pony Podcast, we sit down with Lee Springett, a former secondary school teacher who made the leap from the classroom into the charity sector. After 12 years in teaching, Lee didn’t leave because of burnout or a critical incident - he left because of a gut feeling and a reflective process that changed his perspective on what the next 20 years could look like.Lee takes us through the creation of his “list of non-negotiables,” his year-long exit strategy, and the 75 ...

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63:27

022 - Pit Pony Gareth Isaac - Classroom to...

The Pit Pony Podcast - Life After Teaching ·

2025/01/07

In this deeply introspective episode of the Pit Pony Podcast, Sharon and Sarah sit down with Gareth Isaac, a former sociology teacher who left the classroom after 4 years - overwhelmed by exhaustion, stress, and a profound sense of disconnection. Gareth candidly shares how he navigated the physical and emotional toll of burnout, his struggle to recognise what was happening to him, and the journey that followed his decision to leave teaching.Now a mindfulness teacher, Gareth explains how mindf...

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43:26

021 - Pit Pony Jane Lloyd - Classroom to Artist

The Pit Pony Podcast - Life After Teaching ·

2024/12/31

In this final episode of 2024, we welcome Jane Lloyd—a former teacher of 14 years who traded in the classroom for a paintbrush and a new lease on life. Jane’s story is a perfect way to close out the year: a tale of transformation, resilience, and the power of pursuing what truly lights you up.After years of dedicating herself to teaching art in schools, Jane decided she was done with the stress and exhaustion that teaching brought into her life. In July 2024, she stepped away from her vocatio...

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25:20

017 - Pit Pony Jonny Millard - Chapter 2 - A Rapid...

The Pit Pony Podcast - Life After Teaching ·

2024/12/24

In Chapter 2 of Jonny Millard's story, we follow his move to a new school with high hopes and ambition. However, unforeseen changes in leadership and department dynamics quickly create a challenging environment.Jonny shares how the arrival of a new head of history marked the beginning of a steady decline in his motivation and mental health. Through microaggressions, a lack of support, and poor management, his workplace became increasingly toxic, leaving him questioning his abilities and self-...

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