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Saturday | November 14, 2026
10-11am Eastern | 7-8am Pacific
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Turn “I feel guilty for leaving” into “It’s okay to choose what’s next.”
Let go of teacher guilt, honor the difference you’re made, and move forward with confidence.
Leaving teaching can bring up a lot of emotions, and guilt is often one of the hardest to navigate. Whether you’re worried about leaving your students, letting colleagues down, disappointing others, or walking away from a career you once dreamed of, you’re not alone. In this webinar, we’ll explore where that guilt comes from, how to challenge the beliefs behind it, and how to give yourself permission to want something different. You’ll learn practical strategies for honoring the impact you’ve made as a teacher while letting go of the pressure to justify your decision or make everyone else understand.
Your years in the classroom mattered, and choosing a new path doesn’t erase that impact. Learn how to make peace with your decision, focus on what you need now, and move forward with greater confidence and excitement for what comes next.
YOU CAN CARE DEEPLY AND STILL CHOOSE WHAT’S NEXT.
REAL TEACHERS. REAL PROGRESS.
Register Free for A Limited Time
Join us live and walk away with clarity, confidence, and clear next steps.
Saturday | November 14, 2026
10-11am Eastern | 7-8am Pacific
MOVING FORWARD DOESN’T MEAN LEAVING YOUR VALUES BEHIND.
About Your Coach
Marcia Wall
Global Career
Development Facilitator
Certified Career Services Provider
Save Your Seat (Free)
It’s time to move forward with clarity and confidence.
Saturday | November 14, 2026
10-11am Eastern | 7-8am Pacific
FREQUENTLY ASKED QUESTIONS
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Save Your Seat (Free)
It’s time to move forward with clarity and confidence.
Saturday | November 14, 2026
10-11am Eastern | 7-8am Pacific
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This Session Is No Longer Available — But Don’t Worry!
But check out our current FREE Teacher Transition Career Event!
SAVE MY SPOT!
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.
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.
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.
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 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.
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.
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.
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.
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.
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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Curriculum Designer
Global Career Development Facilitator
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 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.
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.
Director of Solutions Engineering
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.
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.
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.
NOW AVAILABLE!
You Asked.
We Listened.
Limited time Introductory Offer + Member Discount!
Limited spots available -
book before pricing goes up!
NOW AVAILABLE!
You Asked.
We Listened.
Limited time Introductory Offer + Member Discount!
Limited spots available -
book before pricing goes up!
Former Educator
Chelsea Maude Avirett is a former educator and the founder of Skip’s Job Board, a curated platform designed to help educators find roles that align with their skills and experience. After experiencing firsthand how time-consuming and overwhelming the job search process can be, she launched the platform in 2021 to streamline access to relevant opportunities.
Since then, Chelsea has curated over 20,000 education-adjacent roles, helping job seekers identify positions across both major companies and smaller organizations. She also has extensive experience interviewing candidates across a range of roles and regularly shares insights on hiring trends in EdTech and Learning & Development through podcasts and professional speaking engagements.
Former Educator
Nate Ditterline is a former educator with over 15 years of instructional experience and now serves as a Supervisor for Expanse Trainers, supporting technical training for a new software rollout. After transitioning out of the classroom, Nate has focused on training development, onboarding, and leadership support—helping teams successfully adopt new systems and processes.
Throughout his career, he has trained over 400 leaders, co-developed and facilitated leadership programs, and led large-scale training initiatives. Nate brings a practical, collaborative, and people-centered approach to training, along with a strong background in curriculum implementation and professional development.
management.
Former Educator
Gina Arnello made the decision to pursue a new path that aligned with her passion for accessibility, communication, and problem-solving after 20 years as a special education teacher. With support from the Teacher Career Transition Academy, she successfully transitioned into her current role as an Assistive Technology Specialist.
In her role, Gina works with individuals with disabilities, families, and support teams to expand communication access and implement tools such as AAC and other assistive technologies. She is passionate about helping others find practical, individualized solutions and is excited to share her journey with educators exploring what’s next.
Former Educator
Denise Treadway spent 29 years as an elementary classroom teacher before retiring from education in 2025 and beginning a new chapter in her career. She now works as an Estimator for Texas Site Services, a locally owned pavement striping and sweeping company.
Denise’s transition highlights that it’s never too late to make a change. In addition to her current role, she serves on the Board of Education for Shepherd of the Hills Lutheran School and Childcare. She brings a thoughtful, steady perspective to the transition process and is excited to share what it’s looked like to start something new after a long career in education.
Transitioning Educator
Renee Jackson is currently in the “messy middle” of her career transition after more than a decade in education. She teaches English as an Additional Language and brings a diverse professional background that includes experience as a computer programmer, homeschooling parent, and international educator.
After teaching in Costa Rica, Hong Kong, and now in the U.S., Renee recently made the decision to explore new career opportunities. Since joining the Teacher Career Transition Academy, she has been actively applying to roles, gaining traction, and beginning to receive callbacks. Renee brings a real-time, honest perspective on what it looks like to navigate change while still in the classroom.
Special Education Teacher
Rachel Dunbar is a special educator with over eight years of experience supporting diverse learners and leading professional development in K–12 schools. She is currently transitioning into the EdTech space, exploring roles in implementation, onboarding, and professional learning.
Through her journey, Rachel has leaned into the support of the Teacher Career Transition Academy, where coaching, mindset work, and community have helped her build confidence and strengthen her interview skills. She brings a thoughtful, reflective perspective to the transition process, along with a creative edge as a stand-up comedian and show producer.
Transitioning Educator
Samara Birkey is currently balancing roles as a high school civics teacher and office administrator while exploring new career opportunities beyond the classroom. Her passion for culture, history, and technology has shaped her approach to teaching and continues to influence her next steps.
Known for her strong work ethic, adaptability, and problem-solving mindset, Samara is actively building momentum in her transition. She brings a grounded, thoughtful perspective to the “messy middle” and is committed to finding a path that aligns with both her skills and long-term goals.