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#110: The Messy Middle: How Sally Found Her New Path, One Step at a Time
What if the hardest part of your career transition… is how long it takes?
For Sally Del Llano, the decision to leave teaching didn’t happen overnight. After nearly two decades in special education, she knew as early as 2016 that she couldn’t sustain the pace long-term.
But it would take eight more years of planning, saving, and navigating real-life responsibilities before she was finally able to step away from the classroom.
In this Messy Middle conversation, Sally shares what it really looks like to transition careers over time and why a nonlinear path doesn’t mean you’re doing it wrong.
From discovering new interests during a sabbatical, to landing a part-time “bridge role” that helped clarify her direction, to learning entirely new skills in her late 40s—her journey is a powerful reminder that progress doesn’t have to be fast to be meaningful.
We talk about:
✨ Why career transitions often take longer than you expect
✨ How to move forward without a perfectly mapped-out plan
✨ The role of “bridge jobs” in building clarity and confidence
✨ What it looks like to balance family, finances, and career change
✨ And how to navigate the overwhelm of modern job searching
If you’ve ever felt stuck, behind, or unsure if you’re doing this “right”…. This episode will remind you that there’s no one path forward, only the one you keep choosing.
Links from Episode:
» Connect with Sally: http://www.linkedin.com/in/sally-del-llano
» Join my Free Masterclass: Click here to jumpstart your career transition journey.
» 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!
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By Teacher Career Transition AcademyWhat if the hardest part of your career transition… is how long it takes?
For Sally Del Llano, the decision to leave teaching didn’t happen overnight. After nearly two decades in special education, she knew as early as 2016 that she couldn’t sustain the pace long-term.
But it would take eight more years of planning, saving, and navigating real-life responsibilities before she was finally able to step away from the classroom.
In this Messy Middle conversation, Sally shares what it really looks like to transition careers over time and why a nonlinear path doesn’t mean you’re doing it wrong.
From discovering new interests during a sabbatical, to landing a part-time “bridge role” that helped clarify her direction, to learning entirely new skills in her late 40s—her journey is a powerful reminder that progress doesn’t have to be fast to be meaningful.
We talk about:
✨ Why career transitions often take longer than you expect
✨ How to move forward without a perfectly mapped-out plan
✨ The role of “bridge jobs” in building clarity and confidence
✨ What it looks like to balance family, finances, and career change
✨ And how to navigate the overwhelm of modern job searching
If you’ve ever felt stuck, behind, or unsure if you’re doing this “right”…. This episode will remind you that there’s no one path forward, only the one you keep choosing.
Links from Episode:
» Connect with Sally: http://www.linkedin.com/in/sally-del-llano
» Join my Free Masterclass: Click here to jumpstart your career transition journey.
» 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!