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The Classroom Exit Strategies Podcast

The Classroom Exit Strategies Podcast

Written by: Jennifer Holt
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A podcast for teachers who are thinking about leaving the classroom to pursue a different career path or are simply curious about starting a teacher side hustle. Discover what you need to have in place BEFORE you resign from your teaching job including how to best replace your teaching salary outside of the classroom, the best jobs for teachers who don't want to teach, what you need to know about your teacher retirement, and how to find appropriate health insurance. We'll also dive into topics like how your mindset is holding you back, how to get more done in the small amount of time you have outside of the classroom, whether you need to create a teacher LLC, and how to cultivate a self-sustaining business that you love OUTSIDE of the classroom! Find amazing guest interviews with some of the biggest names in education who have left the classroom and have thriving businesses, teachers who are still in the classroom and have booming teacher side businesses, as well as experts in the fields of law, business, and accounting so that you are prepared to take the next step successfully.© 2025 The Classroom Exit Strategies Podcast Economics Leadership Management & Leadership
Episodes
  • How Much Do Teachers Charge for Tutoring: How to Charge More
    Oct 2 2023

    With increasing learning deficits observed in students since 2020 and increasing demand for personalized education, teachers have become a vital resource for students seeking extra academic support.

    In fact, tutoring has become a relevant source of income for many teachers. But that begs the question, How much do teachers charge for tutoring?

    Well that's a great question, but to figure out what your private tutor rates would be, we need to pull back the curtain on what other factors need to be considered.

    While we know tutoring is an excellent way for students to gain more in-depth knowledge of a subject, strengthen their academic skills, and improve their academic performance, it is also a lucrative option for teachers who want to supplement their income or take the first step in their exit strategy from the classroom.

    📝 Click here for a transcript of this episode.


    Links mentioned in this episode:

    • Website Design Services
    • One-on-One Coaching

    Follow me on IG @classroom_exit_strategies

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    14 mins
  • Best Ecommerce Plugins for Wordpress You Need
    Mar 30 2023

    If you have a TpT shop or have considered starting one, you’ve probably heard talk about some of the issues that have arisen on the TpT platform regarding search issues, security concerns, and the acquisition of TpT by the IXL platform.

    And each of those can be super-terrifying, which is why many teachers are running scared. They are fearful…

    1. their income is going to tank, and
    2. all of their work will be for nothing

    Therefore, many have decided to add an e-commerce shop to their own websites in order to sell their resources.

    And if you've been listening to any of these conversations, one e-commerce solution is garnering a lot of attention in the teacher entrepreneur space…and that is WooCommerce.

    I personally have a WooCommerce shop, but that is getting ready to change.

    Why, you might ask?

    Well, I reached out to my "go to" tech guy, Grayson Bell founder and CEO of iMark Interactive, with a couple of questions about setting up a WooCommerce shop for a client...

    And he dropped a bomb on me when he said, "To be honest, Woo is such a terrible e-com system. I wouldn't recommend it for anyone anymore."

    To say I was shocked would be a gross understatement.

    After recovering from that startling revelation, I knew I had to ask if he would be willing to come on the podcast and share his insight, reasoning, and suggestions for teacher entrepreneurs.

    And trust me when I tell you that if the tech side of starting a blog or website scares you, then this is the guy you want in your corner.

    So he is here today to share all of his insight regarding Woo Commerce and which e-commerce solution is going to be the best for teacher entrepreneurs.

    📝 Click here for a transcript of this episode.

    Follow me on IG @classroom_exit_strategies

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    24 mins
  • 15 of the Best Career Changes for Teachers
    Mar 16 2023

    Making a career change can be a scary prospect! The reality is most of us choose a career path and plan to stay the course until we retire.

    But if you’re feeling more and more convinced that you need to pursue other options, then this podcast is for you.

    Today we are going to explore the best career changes for teachers who want out of the traditional classroom and are actively seeking other alternatives.

    Now I know we’ve spent time touching on the topic of seeking a new career path before, but today we’re going to look at...

    • 15 of the best jobs for teachers that capitalize on your transferable skills and your experience in the education field,
    • why they are each considered the best career change for teachers,
    • and how to determine which one you should pursue.

    So if you’re ready, let’s do it!

    📝 Click here for a transcript of this episode.

    Follow me on IG @classroom_exit_strategies

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    17 mins
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