What happens when the career you worked so hard to build turns out to be the wrong fit?

After a successful career in nonprofit fundraising, Emily Cunningham followed her passion into teaching.

But despite loving her students, she quickly realized the classroom was taking a toll on her health, energy, and family life.

In this episode of The Messy Middle, Emily shares why she made the difficult decision to resign after three years—and what she's learning as she explores her next chapter.

We talk about:

✨ Why loving your students doesn't always mean teaching is the right fit

✨ How to recognize when it's time to listen to yourself

✨ Finding career clarity by focusing on your strengths and what brings you joy

✨ Using ChatGPT to strengthen your resume and job applications

✨ Why career coaching is about more than landing your next job

If you've ever wondered whether the career you chose is still the career you want, Emily's story is a reminder that it's okay to choose a different path.

Links from Episode:

» Connect with Emily: https://www.linkedin.com/in/emily-cunningham-4846649/

» Join our next free coaching call: https://www.teachercareertransitionacademy.com/teacher-transition-career-event?data-cst=podcast

» Book a 1:1 LinkedIn Review: https://www.teachercareertransitionacademy.com/teacher-li-profile-review

» Keep Learning With Me: Discover the Teacher Career Transition Academy
» Join our FB Group: A thriving community of support and resources.
» Download the Career Directory: Discover over 200+ alternative careers.
» “I love Lisa and the Teacher Career Transition Podcast” If this sounds like you, please consider rating and reviewing my show! This helps me support more people – just like you – find happiness in a new career. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review”.
» Also, if you haven’t done so already, follow the podcast. I’m adding special surprises to the feed, and if you aren’t following, you have a good chance of missing out! Follow now!

Teachers have a lot of transferable skills.

That isn’t usually the problem. The bigger challenge is knowing which skills actually matter for the job you want, and helping a hiring manager immediately see the connection.

In this episode, Lisa Harding explains the difference between simply having transferable skills and strategically aligning your experience to a target role.

You’ll learn:

• Why “I have transferable skills” isn’t enough
• The difference between a transferable skill and an aligned skill
• Why more skills do not necessarily create stronger positioning
• Why you don’t need to be a 100% match for a job

Your job isn’t to convince an employer that teachers can do everything. Your job is to make it easy for them to see why you can do this job.

Links from Episode:
» Join our next free coaching call: https://www.teachercareertransitionacademy.com/teacher-transition-career-event?data-cst=podcast» Book a 1:1 LinkedIn Review: https://www.teachercareertransitionacademy.com/teacher-li-profile-review
» Keep Learning With Me: Discover the Teacher Career Transition Academy
» Join our FB Group: A thriving community of support and resources.
» Download the Career Directory: Discover over 200+ alternative careers.
» “I love Lisa and the Teacher Career Transition Podcast” If this sounds like you, please consider rating and reviewing my show! This helps me support more people – just like you – find happiness in a new career. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review”.
» Also, if you haven’t done so already, follow the podcast. I’m adding special surprises to the feed, and if you aren’t following, you have a good chance of missing out! Follow now!

Are you putting time into your career transition but still feeling like you’re not getting anywhere?

You may be doing the right things — just in the wrong order.

In this episode, Lisa Harding walks through the career-transition sequence she recommends for teachers and explains why updating your resume or sending applications often shouldn’t be your first step.

You’ll learn:

• Why so much of your career-transition work happens before you ever apply
• The four stages of a teacher career transition
• Three questions that can help you narrow your career options
• How to identify the skills you’re both good at and actually enjoy using

If you want to be ready when the right opportunity appears, the goal isn’t to rush to the application.

It’s to make sure you’re doing the right work in the right order.

Links from Episode:
» Join our next free coaching call: https://www.teachercareertransitionacademy.com/teacher-transition-career-event?data-cst=podcast» Book a 1:1 LinkedIn Review: https://www.teachercareertransitionacademy.com/teacher-li-profile-review
» Keep Learning With Me: Discover the Teacher Career Transition Academy
» Join our FB Group: A thriving community of support and resources.
» Download the Career Directory: Discover over 200+ alternative careers.
» “I love Lisa and the Teacher Career Transition Podcast” If this sounds like you, please consider rating and reviewing my show! This helps me support more people – just like you – find happiness in a new career. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review”.
» Also, if you haven’t done so already, follow the podcast. I’m adding special surprises to the feed, and if you aren’t following, you have a good chance of missing out! Follow now!