Sharon Cawley and Sarah Dunwood
The Pit Pony Podcast - Life After Teaching
Sharon Cawley and Sarah Dunwood talk to former teachers about exiting from the classroom and thriving. Follow us on Facebook https://www.facebook.com/ThePitPonyPodcast Don't forget to leave us a VOICEMAIL, quickly and easily at https://www.speakpipe.com/pitponypodcast Support the podcast by buying us a coffee here: https://buymeacoffee.com/thepitponyclub
Author
Sharon Cawley and Sarah Dunwood
Category
Podcast website
Latest episode
Dec 23, 2025
Where to listen?
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Episodes
037 - Pit Pony Hollie Jones - Classroom to Neurodivergent Educator - Part 2 04.03.2025 1:34:22
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 documente...
035 - Pit Pony Ruth O'Neill - Classroom to SEND Consultant and Tutor 25.02.2025 1:02:46
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...
034 - Pit Pony Sarah Cowen - Classroom to Head of Domestic Abuse Services 18.02.2025 1:11:03
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,...
033 - Sliding Doors Stories - Part 5 14.02.2025 8:18
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 crea...
032 - Pit Pony Katie Stone - Classroom to Virtual Assistant Agency Owner 11.02.2025 1:06:20
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...
031 - Sliding Doors Stories - Part 4 07.02.2025 7:02
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! 🧘...
029 - Sliding Doors Stories - Part 3 31.01.2025 19:37
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. ✨ H...
028 - Pit Pony Mark Thompson - Classroom to TV & Film Chaperone 28.01.2025 39:43
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 t...
027 - Sliding Doors Stories - Part 2 24.01.2025 6:13
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 Author Rowena...
025 - Pit Pony Leanne Herring - Classroom to Voice Artist and Content Creator - PART 1 21.01.2025 49:35
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 t...
026 - Pit Pony Leanne Herring - Classroom to Voice Artist and Content Creator - PART 2 21.01.2025 41:53
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, i...
024 - Sliding Doors Stories - Part 1 17.01.2025 9:24
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 h...
023 - Pit Pony Lee Springett - Classroom to Barnardos Project Manager 14.01.2025 1:08:42
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 take...
022 - Pit Pony Gareth Isaac - Classroom to Mindfulness Teacher 07.01.2025 1:03:27
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...
021 - Pit Pony Jane Lloyd - Classroom to Artist 31.12.2024 43:26
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 a...
016 - Pit Pony Jonny Millard - Chapter 1 - The Teacher Who Dreamed Big 24.12.2024 26:12
Welcome to a very special Christmas special 5 part episode of the Pit Pony Podcast. In this first chapter of Jonny Millard’s compelling story, we meet an ambitious young history teacher from the Midlands. With dreams of becoming a headteacher, Jonny entered the profession full of passion, eager to make a difference and climb the ranks of leadership. But by 2019, his journey had taken an unexpected...
017 - Pit Pony Jonny Millard - Chapter 2 - A Rapid Decline 24.12.2024 25:20
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 po...
018 - Pit Pony Jonny Millard - Chapter 3 - Reaching Out For Help 24.12.2024 21:38
In Chapter 3, Jonny Millard takes a courageous step as he reaches out for help, sharing his growing struggles with colleagues and leadership. Determined to salvage the passion he once had for teaching, Jonny recounts his desperate attempts to address the toxic environment that was taking a toll on his mental health. As the story unfolds, Jonny paints a vivid picture of his internal battle, the sys...
019 - Pit Pony Jonny Millard - Chapter 4 - Breaking Free, The Struggle for a New Beginning 24.12.2024 18:48
In Chapter 4 of Jonny Millard’s story, we delve into one of the most harrowing aspects of his teaching career: the systemic barriers preventing him from leaving a toxic work environment. As Jonny recounts, the reliance on references and the coercive control exerted by his academy left him feeling trapped, unable to secure a fresh start despite his best efforts. With incredible vulnerability, Jonny...
020 - Pit Pony Jonny Millard - Chapter 5 - From The Shadows To Success 24.12.2024 51:51
In this final chapter of Jonny Millard’s gripping story, we witness his extraordinary transformation from being trapped in a toxic work environment to thriving as a successful entrepreneur. Jonny shares how he found freedom after leaving teaching, rediscovering his purpose and channeling his drive into building a thriving business. Through sheer determination and resilience, Jonny turned his skill...
015 - Hannah Jones - Classroom to Head of Prison Education England & Wales 17.12.2024 1:20:18
In this heart-wrenching yet uplifting episode of the Pit Pony Podcast, we sit down with Hannah Jones, a former teacher whose passion for education carried her from the classroom to an extraordinary role as Head of Prison Education for England and Wales. Hannah’s story is one of resilience, determination, and transformation. With a family background rooted in education and years of teaching both ab...
014 - Pit Pony Rae Dillon - Classroom to Copywriter 10.12.2024 35:56
After 17 years in education, Rae Dillon made a bold decision to leave the classroom and step into a whole new world. In this episode, Rae shares her fascinating journey from teaching in the UK and China to becoming a successful copywriter, editor, and proofreader with her own business. Discover how teaching abroad gave Rae a unique perspective on education, why two and a half days of supply teachi...
013 - Pit Pony Nicole Bateman - Classroom to SEND Advisor & Sensory Expert 03.12.2024 1:01:10
After 11 years in the classroom, Nicole Bateman left teaching in 2021, seeking a new way to align her career with her family's needs and her personal passions. Today, she’s thriving as the Friendly SEND Advisor, making children’s activities more inclusive for those with special educational needs. Nicole shares her powerful journey, including the life-altering incident that shook her confidenc...
012 - Pit Pony Amy Meade - Classroom to Learning & Development Manager 26.11.2024 1:10:41
After 14 years in teaching, from secondary English to primary leadership roles, Amy Meade’s journey out of the classroom is remarkable. Amy candidly shares the burnout that came with Ofsted pressures, the life-changing realisation that school didn’t have to own her, and how she stepped into a new career as a Learning and Development Manager. Through over 400 job applications, Amy’s resilience an...
011 - Pit Pony Rowena Hicks - Classroom to Author 19.11.2024 49:11
Today, we’re joined by Rowena Hicks , who dedicated over 30 years to her role as a Deputy Head Teacher and SENCO in the London-Kent area. Teaching was Rowena's life - it was her passion, her calling, and she gave it her all, right up until the moment her own health signalled it was time to step back. Rowena opens up about the physical and emotional toll of being a people-pleaser in the world...
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