JUNE 3, 2025 by Lisa
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#054: What It Really Takes to Change Careers as a Teacher
with Lisa Harding
You’ve seen the posts:
“Excited to announce my new role outside the classroom!”
But what you don’t see?
The messy, emotional, and often confusing journey it took to get there.
In this episode, Lisa pulls back the curtain on what it really takes to change careers as a teacher—and why it’s okay if your transition isn’t quick, easy, or linear. She shares the truth behind the process, common emotional roadblocks, and the power of hearing real stories from teachers who’ve made the leap.
You’ll learn:
• Why career change is so much more than just a resume update
• What to expect in the “messy middle” of transition
• How hearing others’ stories can unlock clarity and confidence
• Why networking matters—and how to start with simple steps
• A sneak peek at the powerful panel coming to the June 14 Teacher Career Transition Summit
🎉 Want to hear real stories from former teachers who made the leap?
Join us for “How They Did It: Real Career Change Stories from Former Teachers”—a live panel at the Teacher Career Transition Summit featuring Katie Fielding, Amy Donato, and Holly Owens.
🎟️ Register free (or grab the replay if it’s passed) at:
This episode will remind you that you’re not alone—and you’re more capable than you think.
≫ Teacher Career Transition Summit: www.TeacherCareerTransitionAcademy.com/summit
≫ Download the Career Directory: Discover over 200+ alternative careers.
≫ Teacher Career Transition Academy: www.teachercareertransitionacademy.com
≫ “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!
≫ Teacher Career Transition Academy: www.teachercareertransitionacademy.com
≫ “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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Deiera Bennett
LinkedIn Strategist
Deiera Bennett is the owner of Career Confidence by Dee. She uses her 6+ years of marketing, writing, and education experience to teach jobseekers how to market themselves for new careers. Deiera currently works for a branding agency as a LinkedIn Strategist & Ghostwriter for CEOs. Whether you’re a teacher or a CEO, her goal is to help you confidently communicate your value to your audience.
LinkedIn Strategist
Deiera Bennett is the owner of Career Confidence by Dee. She uses her 6+ years of marketing, writing, and education experience to teach jobseekers how to market themselves for new careers. Deiera currently works for a branding agency as a LinkedIn Strategist & Ghostwriter for CEOs. Whether you’re a teacher or a CEO, her goal is to help you confidently communicate your value to your audience.
Charissa Stowers
Corporate Learning & Development Executive
Charissa Stowers is an experienced senior level Learning and Development Director. Charissa has a proven track record of development and launch of innovative, industry leading programs that help people ENJOY learning. She has experience hiring and managing teams within the L&D space. With over 15 years of career experience in the technology field, she has had many roles at various companies. She’s worked at small tech startups, and at large international companies such as Apple and Pandora/Sirius XM.
Corporate Learning & Development Executive
Charissa Stowers is an experienced senior level Learning and Development Director. Charissa has a proven track record of development and launch of innovative, industry leading programs that help people ENJOY learning. She has experience hiring and managing teams within the L&D space. With over 15 years of career experience in the technology field, she has had many roles at various companies. She’s worked at small tech startups, and at large international companies such as Apple and Pandora/Sirius XM.
Kate Hutson
Life & Career Coach
Kate Hutson is a Life & Career Coach providing trusted coaching for professional women to show up with confidence and take control of their careers. After a decade of passionate work as a business leader, teacher, and coach, Kate turned her passion for mentoring others into practical knowledge for the real world– skills that women can use in their everyday lives to achieve their long-term career goals and live with more joy, energy, and fulfillment.
Life & Career Coach
Kate Hutson is a Life & Career Coach providing trusted coaching for professional women to show up with confidence and take control of their careers. After a decade of passionate work as a business leader, teacher, and coach, Kate turned her passion for mentoring others into practical knowledge for the real world– skills that women can use in their everyday lives to achieve their long-term career goals and live with more joy, energy, and fulfillment.
Rachel Serwetz
Career Exploration Coach & CEO @WOKEN
Rachel Serwetz’ early professional experience was at Goldman Sachs in Operations and at Bridgewater Associates in HR. From there, she was trained as a coach at NYU and became a certified coach through the International Coach Federation. After this, she worked in HR Research at Aon Hewitt and attained her Technology MBA at NYU Stern. Throughout her career, she has helped hundreds of professionals with career exploration and for the past 4.5 years she has been building her company, WOKEN, which is an online career exploration platform to coach professionals through the process of clarifying their ideal job and career path. She is also an Adjunct Professor of Entrepreneurship at Binghamton University and has served as a Career Coach through the Flatiron School/WeWork, Columbia University, and Project Activate. Learn more about WOKEN here: iamwoken.com.
Career Exploration Coach & CEO @WOKEN
Rachel Serwetz’ early professional experience was at Goldman Sachs in Operations and at Bridgewater Associates in HR. From there, she was trained as a coach at NYU and became a certified coach through the International Coach Federation. After this, she worked in HR Research at Aon Hewitt and attained her Technology MBA at NYU Stern. Throughout her career, she has helped hundreds of professionals with career exploration and for the past 4.5 years she has been building her company, WOKEN, which is an online career exploration platform to coach professionals through the process of clarifying their ideal job and career path. She is also an Adjunct Professor of Entrepreneurship at Binghamton University and has served as a Career Coach through the Flatiron School/WeWork, Columbia University, and Project Activate. Learn more about WOKEN here: iamwoken.com.
Alyson Garrido
Career Coach
Alyson Garrido is passionate about supporting professionals to advance their careers and find jobs they will enjoy. As a career coach, she partners with her clients to identify their strengths and create a path toward a more fulfilling career. Alyson provides support around interview preparation, performance reviews and salary negotiations, ensuring that her clients present themselves in the best possible light. Learn more or book a session with Alyson by visiting www.alysongarrid.com.
Career Coach
Alyson Garrido is passionate about supporting professionals to advance their careers and find jobs they will enjoy. As a career coach, she partners with her clients to identify their strengths and create a path toward a more fulfilling career. Alyson provides support around interview preparation, performance reviews and salary negotiations, ensuring that her clients present themselves in the best possible light. Learn more or book a session with Alyson by visiting www.alysongarrid.com.
Annie Dean
Customer Success Executive/CEO
Annie Dean (she/her) is CEO and Cofounder of RecastSucces; working to diversify the tech industry by helping career transitioners, supporting mentorship, and Fractional Head of Success leadership for SaaS startups. She is also a Udemy for Business and Maven instructor. Previously she was a career transitioner herself. She went on to Customer Success leadership and executive roles at LinkedIn, Coursera, and several startups. She is a wife and mom living in a rural community near Yosemite.
Customer Success Executive/CEO
Annie Dean (she/her) is CEO and Cofounder of RecastSucces; working to diversify the tech industry by helping career transitioners, supporting mentorship, and Fractional Head of Success leadership for SaaS startups. She is also a Udemy for Business and Maven instructor. Previously she was a career transitioner herself. She went on to Customer Success leadership and executive roles at LinkedIn, Coursera, and several startups. She is a wife and mom living in a rural community near Yosemite.
Lisa Harding
EdTech Executive | CEO of LearnWorld
Lisa Harding is a former EdTech Executive with over 15 years of experience driving growth and innovation in the EdTech market. Most recently, Lisa served as President of SimpleK12, an online professional development company for K-12 educators. Prior to serving as the company President, Lisa held roles in product/content marketing and development, eCommerce, and sales. Lisa has dedicated her career to providing award-winning training and development to classroom teachers. She has also interviewed and hired many career changers – specifically teachers! Throughout her career in the EdTech industry, Lisa has demonstrated strong leadership, a passion for educators, and a deep commitment to providing best-in-class online courseware. Lisa now serves as Co-Founder and CEO of LearnWorld.
EdTech Executive | CEO of LearnWorld
Lisa Harding is a former EdTech Executive with over 15 years of experience driving growth and innovation in the EdTech market. Most recently, Lisa served as President of SimpleK12, an online professional development company for K-12 educators. Prior to serving as the company President, Lisa held roles in product/content marketing and development, eCommerce, and sales. Lisa has dedicated her career to providing award-winning training and development to classroom teachers. She has also interviewed and hired many career changers – specifically teachers! Throughout her career in the EdTech industry, Lisa has demonstrated strong leadership, a passion for educators, and a deep commitment to providing best-in-class online courseware. Lisa now serves as Co-Founder and CEO of LearnWorld.
Shannon Schwaebler
GCDF, CPRW
Shannon Schwaebler has over eight years of experience in career development and higher education. She has dedicated her career to supporting individuals in navigating their career paths, providing them with the necessary tools and skillset to confidently navigate their career development process. Shannon understands that career paths are not always straightforward and linear. Instead, she believes that success comes from being prepared for the unpredictable and having the ability to adapt to new situations. Her approach to career development is centered around empowering individuals with the skills and knowledge to succeed in their chosen field. Shannon holds a Bachelor’s degree in Chemistry, a Master’s degree in Higher Education, and multiple certifications, including Global Career Development Facilitator, Certified Professional Resume Writer, Certified Program Planner, and AAUW Salary Negotiation trainer.
GCDF, CPRW
Shannon Schwaebler has over eight years of experience in career development and higher education. She has dedicated her career to supporting individuals in navigating their career paths, providing them with the necessary tools and skillset to confidently navigate their career development process. Shannon understands that career paths are not always straightforward and linear. Instead, she believes that success comes from being prepared for the unpredictable and having the ability to adapt to new situations. Her approach to career development is centered around empowering individuals with the skills and knowledge to succeed in their chosen field. Shannon holds a Bachelor’s degree in Chemistry, a Master’s degree in Higher Education, and multiple certifications, including Global Career Development Facilitator, Certified Professional Resume Writer, Certified Program Planner, and AAUW Salary Negotiation trainer.
Holly Owens
Director of Growth Marketing
Yellowdig
Former Educator
Holly Owens is a former educator turned edtech and instructional design leader, with over 18 years of experience at the intersection of education, technology, and marketing. As Director of Growth Marketing at Yellowdig, she helps organizations create meaningful, people-first learning experiences.
She also serves as an Adjunct Professor at Touro University, preparing future instructional designers to thrive in today’s digital learning landscape. Holly hosts the EdUp L&D podcast, where she spotlights the voices and innovations shaping the future of learning—with a strong focus on accessibility, inclusion, and impact.
Reba Gordon Matthews
Educational Consultant, Speaker
Former Educator
Reba Gordon Matthews is an Educational Consultant with Houghton-Mifflin-Harcourt and a a Freelance Coach and Instructional Designer creating eLearning and learner experience courses. She has over 20 years of elementary teaching experience and has served as an adjunct instructor for Early Childhood Education courses. She holds a Masters in Educational Technology and a Masters in Instructional Design.
As a way of “Paying It Forward,” Reba is also the co-founder and Executive Director of The Jamal Gordon-Hill Foundation. This small family organization supports at-risk young people with academic tutoring, technology training, and college scholarships.
Educational Consultant, Speaker
Former Educator
Reba Gordon Matthews is an Educational Consultant with Houghton-Mifflin-Harcourt and a a Freelance Coach and Instructional Designer creating eLearning and learner experience courses. She has over 20 years of elementary teaching experience and has served as an adjunct instructor for Early Childhood Education courses. She holds a Masters in Educational Technology and a Masters in Instructional Design.
As a way of “Paying It Forward,” Reba is also the co-founder and Executive Director of The Jamal Gordon-Hill Foundation. This small family organization supports at-risk young people with academic tutoring, technology training, and college scholarships.
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From Teacher to
Curriculum Designer
Curriculum Designer
Marcia Wall
Global Career Development Facilitator
Global Career Development Facilitator
Certified Career Services Provider
Marcia coaches individuals to live their best professional lives. Her expertise lies in the areas of career services, coaching, workshop facilitation, and writing. Her coaching style is both holistic and strategic. It is also rooted in DEI principles and practices. She is a Global Career Development Facilitator and a Certified Career Services Provider through the National Career Development Association. She is also certified through Recovery Innovations International to support people with a recovery mindset. Additionally, she holds a Master of Arts degree in Rhetoric and the Teaching of Writing and is a former English instructor and K-12 teacher.
Amy Donato
Instructional Coaching and Professional Learning @ Elevate K12
Amy Donato is a former middle school science teacher turned instructional coach and professional learning facilitator, passionate about helping educators thrive. After years in the brick-and-mortar classroom, she now supports teachers through practical coaching and engaging PD that builds confidence in teachers and improves instruction for students.
Katie Fielding
Edu. Content manager at Book Creator
Former Educator
Katie Fielding is an educational consultant with 20 years of public school experience. She champions digital accessibility, creativity, and Universal Design for Learning (UDL) in classrooms. Specializing in technology and STEM integration, Katie creates interdisciplinary instructional experiences and shares her expertise through presentations and workshops. Recognized as VSTE Coach of the Year in 2018 and a featured voice at ISTELive 2024, she holds multiple certifications, including UDL Credential 2, ISTE Certification, Google Innovator, and Microsoft Innovative Educator Expert. She is a trainer for the ISTE Certified Educator program, and works for Book Creator as their Educational Content Manager.
Edu. Content manager at Book Creator
Former Educator
Katie Fielding is an educational consultant with 20 years of public school experience. She champions digital accessibility, creativity, and Universal Design for Learning (UDL) in classrooms. Specializing in technology and STEM integration, Katie creates interdisciplinary instructional experiences and shares her expertise through presentations and workshops. Recognized as VSTE Coach of the Year in 2018 and a featured voice at ISTELive 2024, she holds multiple certifications, including UDL Credential 2, ISTE Certification, Google Innovator, and Microsoft Innovative Educator Expert. She is a trainer for the ISTE Certified Educator program, and works for Book Creator as their Educational Content Manager.
Steven Anderson
Director of Solutions Engineering
Director of Solutions Engineering
PowerSchool
Steven W. Anderson is a former educator and nationally recognized voice in educational technology, now serving as Director of Solutions Engineering at PowerSchool. With over a decade of leadership experience supporting schools and districts, Steven helps design strategic solutions that elevate teaching, learning, and digital integration across K–12 systems. At the summit, he’ll share his perspective as former teacher turned hiring manager.
Steven W. Anderson is a former educator and nationally recognized voice in educational technology, now serving as Director of Solutions Engineering at PowerSchool. With over a decade of leadership experience supporting schools and districts, Steven helps design strategic solutions that elevate teaching, learning, and digital integration across K–12 systems. At the summit, he’ll share his perspective as former teacher turned hiring manager.
Steven is also the author of three books, including The Relevant Educator and The Tech-Savvy Administrator, and has received multiple honors including the Bammy Award and Microsoft’s Heroes of Education award.
Nicholas Provenzano
Nicholas Provenzano is a former classroom educator who now leads community and content strategy at SchoolAI, where he trains teachers and develops tools to enhance student learning through AI-powered solutions. With over 20 years of experience as a teacher, consultant, and professional development facilitator, Nicholas is passionate about empowering educators to integrate technology and maker-centered learning in meaningful ways. At the summit, he’ll share his perspective as former teacher making the transition and advice from the “other side” of the hiring table.
Content & Training Manager
SchoolAI
Nicholas Provenzano is a former classroom educator who now leads community and content strategy at SchoolAI, where he trains teachers and develops tools to enhance student learning through AI-powered solutions. With over 20 years of experience as a teacher, consultant, and professional development facilitator, Nicholas is passionate about empowering educators to integrate technology and maker-centered learning in meaningful ways. At the summit, he’ll share his perspective as former teacher making the transition and advice from the “other side” of the hiring table.
Nicholas is also the founder of The Nerdy Teacher, a widely read blog, and a contributor to platforms like Edutopia. His work has been featured on CNN, Education Week, and more. Nicholas holds numerous credentials including Google Certified Innovator, Adobe Education Leader, and Microsoft Minecraft Mentor, and is the author of three best-selling books on makerspaces and project-based learning.
Timothy Gwynn
Director of Global L&D Krispy Kreme
Timothy Gwynn is a former teacher turned corporate learning strategist, currently serving as the Director of Global Learning & Development at Krispy Kreme. With a background that spans education, instructional design, and enterprise training, he now leads global professional development initiatives that prioritize learner engagement and align closely with business goals.
Director of Global L&D Krispy Kreme
Timothy Gwynn is a former teacher turned corporate learning strategist, currently serving as the Director of Global Learning & Development at Krispy Kreme. With a background that spans education, instructional design, and enterprise training, he now leads global professional development initiatives that prioritize learner engagement and align closely with business goals.
At the summit, Timothy will share insights from his journey beyond the classroom—including his experience in hiring and talent development at major brands such as XPO Logistics, Rentokil Steritech, and Krispy Kreme.