The Pit Pony Podcast - Life After Teaching

By: Sharon Cawley and Sarah Dunwood
  • Summary

  • 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/pitponypodcast

    Support the podcast by buying us a coffee here:
    https://buymeacoffee.com/thepitponyclub

    © 2025 The Pit Pony Podcast - Life After Teaching
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Episodes
  • 045 - Pit Pony Ilana King - Classroom to Educational Consultant
    Apr 22 2025

    In this episode, we’re joined by the unstoppable Ilana King - educational consultant, entrance exam specialist, home educator, and all-round powerhouse.

    Ilana’s journey is far from typical. After just two years in the classroom, she knew it wasn’t the right fit - and rather than settle, she built something new. Literally. She created her own nursery from the ground up (on land she negotiated with a secondary school), ran it successfully, then sold it and pivoted again. She home educated her three children for 20 years and now sits at the heart of the tuition community, supporting families through 7+, 8+, and 11+ entrance exams and training other tutors to do the same.

    This episode is a masterclass in self-belief, values-led decisions, and building a career on your own terms. Whether you’re still in the classroom or already planning your escape, Ilana’s story will show you what’s possible when you refuse to be boxed in.

    Highlights include:

    • Why she walked away from teaching after just two years
    • The toxic school culture that helped her make up her mind
    • Building and running two nurseries before age 30
    • Why she home educated her children — and how
    • The secrets of the selective school entrance exam world
    • Creating a sustainable, empowering tutoring business

    Ilana didn’t just leave teaching - she rewrote the script.

    You can find Ilana here:

    Website: Become An Entrance Exam Tutor

    Linkeding: https://linkedin.com/in/educationpathfinder

    Instagram @ilana_trainsentranceexamtutors

    Send us a message.

    Buy Us a Coffee ☕️

    Loving the Pit Pony Podcast?

    We’d be so grateful for your support! We’ve set up a Buy Me a Coffee page where you can make a small donation to help keep the podcast running.

    https://buymeacoffee.com/thepitponyclub


    Voice Message Us: https://www.speakpipe.com/pitponypodcast


    Interested in coming to our conference? https://www.tutorsconference.co.uk


    If you've been affected by any of the issues raised in our podcast there are organisations who can help:

    • Education Support
    • The Samaritans
    • Mind
    • Andy's Man Club


    Join Us:

    • Subscribe to the Pit Pony Podcast
    • Sign up to our mailing list here: http://eepurl.com/i1L5ck

    Thanks for listening 🙏

    Edited with finesse by our Podcast Super Producer, Mike Roberts of Making Digital Real

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    1 hr and 10 mins
  • 044 - Pit Pony Pete Scholes - Classroom to Driving Instructor & Author
    Apr 15 2025

    This week, we’re joined by the brilliant and unassuming Peter Scholes – a man who gave 21 years to the classroom before stepping away when shifting leadership turned a once-thriving school culture into something unrecognisable.

    In this heartfelt episode, Pete shares how the sudden departure of a beloved headteacher triggered a school-wide unraveling, leading to mass staff turnover, a loss of trust, and ultimately, his own departure. Now a successful driving instructor and published author, Pete talks openly about depression, rediscovering confidence, and the transferable skills that still shape his life today.

    ✨ It’s a powerful reminder that when one door closes, others truly do open – sometimes with a pen in one hand and car keys in the other.

    📚 Links to Pete’s books can be found here

    Don’t miss this one.

    Send us a message.

    Buy Us a Coffee ☕️

    Loving the Pit Pony Podcast?

    If our episodes have inspired, supported, or entertained you, we’d be so grateful for your support! We’ve set up a Buy Me a Coffee page where you can make a small donation to help keep the podcast running.

    Every contribution goes toward production costs, ensuring we can continue sharing these powerful stories.

    https://buymeacoffee.com/thepitponyclub


    Voice Message Us:
    You can send us a voice message EASILY, whether it be a question, comment, review or anything you like! And if we like it, we'll feature your message on an upcoming episode.
    https://www.speakpipe.com/pitponypodcast


    If you've been affected by any of the issues raised in our podcast there are organisations who can help (click to access their webpages):

    • Education Support
    • The Samaritans
    • Mind
    • Andy's Man Club


    Join Us:

    • Hit subscribe to the Pit Pony Podcast so you don’t miss future episodes – we’ve got some brilliant stories coming up from teachers wh...
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    44 mins
  • 043 - Pit Pony Rob Newlands - Classroom to Financial Planner - Part 2
    Apr 8 2025

    In Part 2 of this powerful conversation, Rob Newlands takes us through the devastating fallout of his time in headship - and the turning point that changed everything.

    After months of isolation, impossible expectations, and systemic failure, Rob faced a brutal mocksted that delivered the final blow. What followed was a silent breakdown behind closed doors, a desperate call to his GP, and the realisation that he had to leave the profession to survive.

    Rob shares the raw truth about what it feels like to hit rock bottom - the shame, the self-doubt, and the guilt so many teachers carry when they can no longer keep going. But this is also a story of recovery, purpose, and the surprising path he found on the other side of education.

    This episode is a lifeline for anyone who’s been made to feel they’re “not enough,” despite giving everything they had. If you've ever questioned your worth, your resilience, or your ability to start again - Rob’s story is for you.


    Useful links :

    Facebook: Rob Newlands- Financial Planner | Falmouth

    Instagram: https://www.instagram.com/robnewlands.dswm/

    Dean Stevens Wealth Management: https://www.deanstevenswm.co.uk/

    Send us a message.

    Buy Us a Coffee ☕️

    Loving the Pit Pony Podcast?

    If our episodes have inspired, supported, or entertained you, we’d be so grateful for your support! We’ve set up a Buy Me a Coffee page where you can make a small donation to help keep the podcast running.

    Every contribution goes toward production costs, ensuring we can continue sharing these powerful stories.

    https://buymeacoffee.com/thepitponyclub


    Voice Message Us:
    You can send us a voice message EASILY, whether it be a question, comment, review or anything you like! And if we like it, we'll feature your message on an upcoming episode.
    https://www.speakpipe.com/pitponypodcast


    If you've been affected by any of the issues raised in our podcast there are organisations who can help (click to access their webpages):

    • Education Support
    • The Samaritans
    • Mind
    • Andy's Man Club


    Join Us:

    • Hit subscribe to the Pit Pony Podcast so you don’t miss future episodes – we’ve got some brilliant stories coming up from teachers wh...
    Show More Show Less
    1 hr and 30 mins

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