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5 Things I Wish I Knew When I Was Transitioning From Teaching (2025)

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In 2021, I left public education during my fifth year of teaching, not because I stopped caring, but because I couldn’t keep sacrificing my well-being for a system that wasn’t working.


I was exhausted, conflicted, and scared of what life outside the classroom might look like. What I wanted was simple: more time with my family, work that aligned with my values, and space to breathe again.


Today, I work from home, walk my kids to school each morning, and earn more than I ever imagined possible, but it didn’t happen overnight. I made plenty of mistakes along the way.


This guide is for any educator who’s just beginning to wonder: “Is there something else out there for me?” 


The answer is yes.


And I want to help you find it—without the detours I took. Here are 5 things I wish I knew when I started to make the leap.


P.S.


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You Don't Need To Go Back To School

A common myth among teachers looking to transition is that they need to spend thousands of dollars on a new degree.


The reality?


Most teachers already have advanced degrees—and you can absolutely pivot without starting over. The key is to build on what you’ve already done.


I started as a special education teacher, became an educational therapist, and eventually grew into my role as an executive function coach. Each step built on the last.


Instead of going back to school, consider upskilling through short certifications, coaching programs, or practical experience that aligns with your next move.


Your Teaching Experience Is Incredibly Valuable

One of the biggest mistakes I made when leaving teaching was underestimating the value of my experience. I thought I needed to work an entirely new career to earn respect or income outside the classroom.


Here is what I discovered: your teaching background is an asset. Parents are willing to pay a premium for one-on-one support from educators—especially those with experience in special education or supporting students with learning differences.


When I asked a friend for advice on what to focus on next, he said, “Don't you have a Master's Degree in Education?” That was my lightbulb moment.


You don’t need to start over. You can just reframe how you talk about what you already know.


How To Write A Value Proposition

If you’re pivoting careers, your value proposition—how you explain what you do and who you help—is key.


Most people start by thinking about income, but a better approach is to begin with who you want to serve and how you’ll help them. Think about the problems you solve.


Are you helping students get organized?

Supporting parents navigating learning plans?


Try this simple template:


“I help [specific group] overcome [challenge] by teaching them [method], so they feel [outcome].”

This clear structure helps you communicate your worth and stand out in any job application, pitch, or website bio.


You're Not Alone In Your Transition From Teaching

When I started thinking about leaving teaching, I thought I was the only one. I didn’t realize thousands of other teachers were in the same boat and many had already jumped ship and were sharing how they did it.


There are tons of online groups out there filled with people that are going through the same thing as you, and plenty of people who are years ahead in the journey that can help you.


Here are some of the common hashtags to start following content about how to transition from teaching:


Instagram


TikTok


LinkedIn


If you prefer to jump into active forums, Facebook is the best place to hang out for transitioning teachers. Check out these groups:


Facebook Groups For Transitioning Teachers (Free)


42.4K members


Group Description:

This group is designed for educators in the United States who are:


- Considering a career change from education

-Exploring new opportunities beyond the classroom

- Already navigating or thriving in a new field


Here, you'll find guidance, encouragement, and a supportive space to share your experiences, ask questions, and exchange ideas. Whether you're just starting to think about your next chapter or have already made the leap, this group is here to help you succeed on your journey.



28.1K members


Group Description:

This group is designed to support and empower educators who are transitioning from traditional teaching roles and seeking exciting new opportunities outside the classroom. Whether you're looking to explore educational technology, curriculum development, instructional design, corporate training, or any other non-teaching path, this community is here to help you navigate your career transition.


There Are Career Coaches Specifically For Teachers

One thing I didn't know is that there are professionals who specialize in guiding former teachers to finding meaningful and profitable careers.


Teacher Career Coach


About:

Founded by Daphne Gomez, a former teacher turned instructional designer, podcaster, and career coach. Daphne and her team help former teachers and HR experts to bring teachers actionable advice and career transition tips. Teacher Career Coach is a community of over 6,000 former and current teachers dedicated to helping you find happiness in your careers, inside or outside the classroom.


Website:


What other resources do they offer for transitioning teachers?



Check It Out On Social Media



Teacher Transition


About:

Teacher Transition is a supportive space for educators who are exploring what’s next. It honors the strengths you built in the classroom and helps you discover how to apply them beyond it—whether you’re ready for a career change now, in the future, or just curious about your options. This isn’t about leaving teaching; it’s about navigating change with clarity, respect, and purpose—wherever your path leads.


Website:


What other resources do they offer for transitioning teachers?



Check It Out On Social Media



The Bottom Line

Once you realize that your teaching experience is an asset and not a limitation—everything else gets easier: your career search, your confidence, your next steps.


Here’s your cheat sheet for navigating a career change:


  • Stop thinking you need another degree

  • Start exploring how your skills transfer

  • Join communities of teachers who’ve already made the leap

  • Craft a value proposition that reflects who you help and how

  • Get support—don’t try to figure this all out alone


Hope this helps! 🤙🏻


Want support in transitioning from teaching?


Consider joining hundreds of educators and professionals who have completed our executive function coaching certification and are building profitable executive function coaching practices using their teaching experience.


You'll gain all the tools, templates, and techniques you'll need as a coach, plus you'll make new friends and have a community you can rely on to grow and learn. Learn more.


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About Me

A white man in a cream sweater and jeans sits smiling against a brick wall, giving a relaxed and content vibe in an outdoor setting.

Hey! I'm Sean 👋


I'm a former public school special education teacher who realized that executive function skills are more important than knowing when George Washington crossed the Potomac.


Since then, I've made it my mission to teach anyone who will listen about how to develop these key life skills.


In 2020, I founded Executive Function Specialists to ensure all students with ADHD and Autism have access to high-quality online executive function coaching services. We offer online EF coaching and courses to help students and families.


Realizing I could only reach so many people through coaching, in 2021 I started the Executive Function Coaching Academy which trains schools, educators, and individuals to learn the key strategies to improve executive function skills for students.


In 2023, I co-founded of UpSkill Specialists, to provide neurodivergent adults with high-quality executive function coaching services.


When not pursuing my passions through work, I love spending time with my family, getting exercise, and expanding my brain through reading. You can connect with me on LinkedIn.

 
 
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