The Pit Pony Podcast - Life After Teaching

080 - Resignation - The Fear, the Finances, and the Freedom


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In this special episode, Sharon and Sarah hold space for one of the biggest topics in education - the mystery, the pressure and the fear around teacher resignation dates.

Why do teachers only get three windows a year to resign? What happens if you miss the May 31st deadline? And why does this system leave so many feeling trapped, anxious and powerless?

From the realities of the Burgundy Book to the emotional and financial toll of leaving a “job for life,” this conversation is honest, supportive and packed with insight. Sharon and Sarah share their own experiences, the tough love advice they give inside the Pit Pony community, and the practical steps teachers can take to reclaim control of their lives and careers.

They explore:

  • What resignation windows actually mean
  • The fear of missing the deadline - and what to do if you do
  • How to plan financially and emotionally before you leave
  • Why guilt, shame and loyalty often hold teachers back
  • When it’s too soon (or too late) to resign

A grounded, empowering conversation for anyone standing at the edge of a big decision.

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

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The Pit Pony Podcast - Life After TeachingBy Sharon Cawley and Sarah Dunwood