In this conversation, Kristin and Hillary explore a critical yet often overlooked aspect of transitioning from the classroom to online entrepreneurship: the importance of building community and relationships. While the independence of online business offers freedom, it can sometimes lead to feelings of isolation. This episode delves into why community is essential for both personal fulfillment and business success. 

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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Join Kristin and Hillary for a celebratory episode to mark the Teachers Make the Leap one-year anniversary. In this episode, Kristin and Hillary recap the years top 5 most-listened-to episodes, marking notable moments and key takeaways from each episode.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of Teachers Make the Leap, Kristin and Hillary tackle a frequently asked listener question: Should I start a product-based business, such as selling digital templates or courses, or opt for a freelance, skills-based business?

In this conversation, we explain why service-based freelance businesses are the best option for teachers who are new to entrepreneurship, touching on the more immediate income potential, the valuable learning and feedback you gain working directly with clients, and the options to scale your business in the way you want to.

We're also discussing the hidden challenges of product-based businesses, such as the significant upfront effort required to build an audience and develop products—tasks that often go unpaid and unrecognized in the early stages.

This episode is a must-listen for any teacher considering entrepreneurship, as it lays out a clear, manageable path to business ownership that aligns with the skills and circumstances unique to educators. Tune in to understand why starting as a freelancer is a smart, strategic move that can set you up for long-term entrepreneurial success.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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Tune in to this episode of the podcast to discover how you can practice your freelance skills before you start your business. This episode is a must-listen for teachers who are interested in starting a freelance business but don't yet feel confident in their skill.

Want to practice with our help?

Skills Lab is a 4-week skill-building workshop for teachers who want to hone their freelance skills in 30 days or less.

*Enrollment is open through May 31st*

Join here!

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In this episode of Teachers Make the Leap, Hillary sits down with Sara Torpey, a former middle school math teacher turned thriving business coach for teachers, helpers, and givers. Sara helps business owners create thriving, profitable businesses by employing simplicity and smart systems. As a multiple business owner, teacher, mom, and wife, Sarah expertly balances various roles while guiding others in the business world, aiming to empower teachers and givers to build businesses they love.

In this conversation, Sarah shares valuable insights about embracing and learning from the unexpected roles we often find ourselves in over the course of our careers, and she emphasizes how skills developed in teaching are not only relevant but highly beneficial in the business realm, preparing teachers for a smoother transition into entrepreneurship.

Connect with Sara:

Website: TorpeyCoaching.com
Facebook Group: UNcomplicating Business for Teachers, Helpers, and Givers
Instagram: @torpeycoaching
LinkedIn: Sara Torpey

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

Join Kristin and Hillary in this episode of Teachers Make the Leap as they discuss one of the most common hurdles faced by new and seasoned freelancers alike: analysis paralysis. 

In this conversation, Kristin and Hillary explore what it feels like to be faced with many different options, and share what the ONLY wrong decision is when it comes to freelance business.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of the Teachers Make the Leap Podcast, Kristin and Hillary tackle a topic that's relevant to both themselves and their students:

The Emotional Rollercoaster of Entrepreneurship

This conversation leaves no stone unturned: Kristin and Hillary are getting real and sharing their thoughts, experiences, and strategies around dealing with the emotional highs and lows of entrepreneurship in the first 6 months to a year of business ownership. 

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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If you're a teacher, chances are you're sitting on a 6-figure skill that you could turn into a freelance business.

In this episode, Kristin and Hillary unpack the 4 most common freelance skills with 6-figure potential. And they explore how most teachers are probably already proficient in at least one of the four.

This episode is a must-listen if you want to replace or exceed your teaching salary working for yourself, but you're not sure where to start. 

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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In this episode, Kristin and Hillary answer a listener's question:

"Between teaching and life stuff, I'm super busy right now. Can I start a business if I'm crunched for time?"

Join Kristin and Hillary as they share their experience starting businesses while teaching and explore practical tips to build a business to replace or exceed your teaching salary even when you're tight on time. 

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode, Kristin and Hillary answer a common question teachers face when they're thinking about starting freelance businesses:

"I have lots of business ideas. How do I choose one?"

Join Kristin and Hillary as they explore what it means to be 'multi-passionate,' the pitfalls of trying to start multiple businesses at once, and how to choose one business idea if you're stuck between a few.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of Teachers Make the Leap, Kristin chats with Tiffany Han, a life coach dedicated to empowering high achievers to experience personal fulfillment. Tiffany provides invaluable insights into the struggle teachers face as they aim to maintain their high-achiever standards while combating burnout in the teaching profession. This conversation explores the intricacies of radical self-belief and offers a framework that can guide listeners through self-discovery and change.

Key Takeaways:

• High achievers often struggle to recognize when enough is enough, which can lead to burnout, but there is a path to establishing a healthier balance.
• Radical self-belief is not about bombastic confidence; it's about trusting in your ability to figure things out, regardless of uncertainty.
• The five pillars of radical self-belief are Discernment, Faith, Spirit Tending, Acceptance, and Grace.
• Engaging in activities that feel nourishing and intentional is a vital component of spirit tending, which is fundamental to cultivating inner wisdom.
• Viewing life's struggles and opportunities as a hike can provide a useful metaphor for understanding actionable steps.

Resources:

Website: TiffanyHan.com
Instagram: @thetiffanyhan
Podcast: The Tiffany Han Show

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And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode, join Kristin as she sits down with Ali Simon and JoDee Scissors, former educators who loved their respective teaching jobs, but ultimately made the decision to shift into new careers.

Together, we'll explore the joys of teaching, the tough emotional transition from the classroom and finding fulfilling work outside of education, and how to think through the question "Who am I if I'm not a teacher?" 

Key Takeaways:

• Teachers considering a career shift face emotional and practical challenges, including how to redefine their professional identity and manage their finances.
• The transition from teaching to a new career can involve updating resumes and professional profiles to better reflect the language and requirements of the new industry.
• Ali and Jodie both emphasize the importance of self-investment through professional help, be it for mental health or financial advice, as a part of the shift from teaching.
• Teaching skills are transferable and valuable in various fields, and the experience as a teacher equips individuals to adapt to new roles effectively.
• Moving away from teaching allows for personal growth and the exploration of multiple facets of one's identity, reaffirming that a job does not solely define an individual.

Resources Mentioned in the Episode:

• Teacher Shift Podcast: teachershiftpodcast.com

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode, Kristin and Hilary talk with Andrea Hanson, a former high school math teacher who spent 12 years in the classroom before saying yes to starting her first business.

Over the last nine years, Andrea has opened and grown multiple businesses including a retail boutique, online coaching business, and podcast to empower women to follow their nudges. 

Listen to the full episode to hear how Andrea took a leap of faith that catapulted her into the world of business where she's found personal fulfillment, time flexibility, and a sense of purpose beyond her wildest dreams.

Key Takeaways:

• Entrepreneurship can be a journey of personal growth and development, requiring you to constantly adapt and reflect inwardly.
• Following your "nudges" or intuitions can lead to unexpected and fulfilling business ventures, even if they challenge the norms of career stability.
• Challenges in transitioning from education to business include managing mindset shifts and adapting to new roles beyond just being an employee.
• Creating a vision and making decisions as if your business goals are already achieved can be a powerful strategy to move forward purposefully.
• Surrounding yourself with a community of like-minded individuals can significantly enhance and impact your entrepreneurial journey.

Follow Andrea on Instagram @andrea.hanson.82 or check our her coaching membership @aligned.business.collective

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To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of Teachers make the Leap, hosts Kristin and Hillary talk with with Chris Collins, a philosophy PhD and former adjunct instructor turned freelance copywriter. 
Together, Chris, Kristin, and Hillary explore the realities of going freelance after working in the traditional academia and secondary education setting.

Key Takeaways:

• Transitioning Skills: Chris’s background in philosophy and his love for writing helped him carve a niche in copywriting for B2B SaaS brands.
• Mindset Shift: Teachers often need a significant shift in mindset about the value of their time and work when transitioning to freelancing.
• Money Mindset: Chris acknowledges the importance of overcoming preconceived notions of what clients will pay, an extension of valuing one’s time.
• Sales Skills: A key skill gap for many teachers moving into freelancing is sales, a necessity for business success.
• Personal Management: Self-care, mental and physical health, and personal development are foundational for business success and cannot be overlooked.

Resources:

• Chris Collins LinkedIn Profile: [Search for Chris Collins on LinkedIn]
• Chris Collins Website: ChristopherCollins Co

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And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of Teachers Make the Leap, Kristin and Hillary chat with guest expert Megan Coulter, a former nurse and educator turned AI mentor to entrepreneurs. Megan shares her insights on the burgeoning realm of AI and how new entrepreneurs can use AI as a powerful tool to grow their businesses.

Key Takeaways:

• Megan's transition from nursing to entrepreneurship illustrates the transformative potential of AI in creating and scaling an online business.
• AI can be an effective tool for generating initial drafts, conducting market research, and exploring creative ideas, saving substantial time for entrepreneurs.
• Teachers possess unique skills that make them particularly adept at utilizing AI to its full potential, including providing feedback and assessing written works.
• Megan's CARE system acts as a comprehensive guide to integrating AI into various business processes.
• The discussion also emphasizes the ethical use of AI and the importance of maintaining human integrity within technological advancements.

Resources:

Free Quickstart Guide: The 6 prompts you need to craft content that connects
Megan's website: www.megancoulteragency.com
Instagram: @itsmegancoulter

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In this episode, Kristin and Hillary chat with Shaun Morgan, a teacher and podcaster dedicated to helping teachers identify their financial superpowers so they can have healthy wallets and financial futures. Sean shares his insights and strategies for teachers to navigate their financial journeys while still fulfilling their passion for teaching.

Key Takeaways:

• Teachers can gain financial control by tracking their spending, avoiding overtime work beyond contract hours, and investing in the retirement options most teachers have.
• Entrepreneurship offers incredible financial growth potential for teachers, especially with flexible summer schedules.
• Educators possess money-saving superpowers like access to multiple pre-tax retirement accounts and the ability to put away significant sums for future financial stability.
• Developing a side business can serve as not only a supplementary income stream but also a refreshing change that helps prevent burnout.

Resources:

• Shaun Morgan's podcast: "Teacher Money Show" (teachermoneyshow.com)
• Sign up for free financial coaching with Sean: teachermoneyshow.com/guest

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode, educators-turned-entrepreneurs Kristin and Hillary sit down with Lauren Bell, who shares her journey from the classroom to launching and running her own online tutoring business. Lauren delves into her extensive experience in special education and her pivotal shift towards helping students with dyslexia through Orton-Gillingham programs. 

Lauren also offers practical insights on building a tutoring business from scratch, emphasizing the importance of adaptability, continuous learning, and leveraging relationships with other professionals to find clients.

Key Takeaways:

• Starting an online tutoring business allowed Lauren Bell to leverage her specialty in Orton-Gillingham programs, addressing a critical need for dyslexia and language-based disability education outside the traditional school environment.
• Teachers possess a wealth of transferable skills, including multitasking, creativity, and data-driven decision-making, that can lead to entrepreneurial success.
• Online business operations and marketing can be intimidating but are learnable and essential skills for growing a tutoring business.
• Establishing a virtual tutoring company has advantages in convenience, flexibility, and access to online resources, while maintaining the need for engaging and effective teaching techniques.
• Adaptation and strategic planning are crucial for business continuity and growth, especially when anticipating personal changes, such as Lauren Bell's experience adjusting her role in her business due to her pregnancy.

Resources:

• Instagram: @hammond_bell
• Facebook: Hammond Bell Educational Services
• Website: www.hammondbell.com

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of "Teachers Make the Leap," Hillary and Kristin welcome special guest Steven Jarvis, a seasoned CPA and tax planner. The conversation dives into the critical transition from W-2 employment to entrepreneurship and the consequent tax implications that educators need to be aware of. You'll hear actionable advice and insightful knowledge to prepare for and manage taxes as you venture into the world of online business.

Key Takeaways:

• Transitioning from W-2 employment to self-employment drastically changes one's tax situation, moving from an almost automatic process to a more manual one.
• New entrepreneurs should set aside a substantial percentage of their income for taxes, potentially upwards of 40%, into a separate savings account.
• Keeping business expenses distinct and well-documented is critical, ensuring that every legitimate business deduction is identified and utilized.
• Making quarterly estimated tax payments is non-negotiable for business owners, and Steven advises a proactive and conservative approach to these payments.
• Despite the daunting nature of tax planning in entrepreneurship, Steven encourages teachers not to allow tax fears to deter them from pursuing their entrepreneurial dreams.

About the Guest:

Steven Jarvis is a Certified Public Accountant (CPA) and a tax planner, who co-founded Retirement Tax Services—a firm specializing in integrating tax planning with financial and retirement planning for financial advisors. With over a decade of expertise as a CPA, Steven is known for his personable approach in the industry, proudly holding the title of "The Least Boring CPA" on LinkedIn. His experience extends to teaching in a master's program and engaging in discussions on tax strategies that are both impactful and informed.

Resources:

LinkedIn Profile: Steven A. (The Least Boring CPA) Jarvis, CPA 🧩
Website: Retirement Tax Services
Podcasts: The Retirement Tax Podcast (consumer-facing), The Retirement Tax Services Podcast (advisor-facing)

IRS Website: For making online estimated tax payments

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of Teachers Make the Leap, Kristin and Hillary delve into the common hurdles that aspiring entrepreneurs encounter when starting their online businesses. They each draw from their personal experiences and interactions with other teachers to identify and break down the barriers to making meaningful progress toward launching a business.

From grappling with decision-making to gaining clarity on the next steps, Kristen and Hillary articulate the challenges many face on their entrepreneurial journey. They emphasize the importance of taking incremental actions, avoiding the pitfalls of perfectionism, and the transformative power inherent in making a series of small yet strategic moves. This discussion covers actionable strategies and the encouragement needed to tackle the often-intimidating task of building a business from scratch.

Key Takeaways:

• New business owners often struggle with committing to key decisions in the beginning due to fear of making the wrong choice.
• Focusing on small, actionable steps, rather than being overwhelmed by the larger vision, can lead to more significant progress over time.
• Overcoming perfectionism is essential; it's better to create a "shitty first draft" and refine later than not to start at all.

Resources:

• The Slight Edge by Jeff Olson
• Shitty First Drafts by Anne Lamott

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

We're taking a break from our regular schedule this week! Want to know why? Listen to find out!

Here are some links you might need:

• Ask a question for the podcast
• Join the Launchpad waitlist

We'll see you back with a regular episode next week.  👀

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

In this episode of Teachers Make the Leap, Kristin and Hilary sit down with Candice Dudley, a former teacher who left the world of education after 10+ years in the classroom to start he own online business as an accountability coach for women. Candice's story offers an honest glimpse into the challenges and motivations that led her from being a dedicated teacher to launching her business. 

This episode is packed with personal anecdotes, tips for women considering big transitions, and practical tips for teachers considering making the leap to entrepreneurship. 

Key Takeaways:

• Making the leap from teaching to entrepreneurship involves overcoming the fear of the unknown and learning to trust personal intuition.
• Building an online business can be achieved through effectively utilizing small pockets of time and breaking down large goals into actionable tasks.
• Transitioning careers can be motivated by the desire for a better work-life balance, especially for teachers who find themselves exhausting their energy in the classroom.
• Skills honed in a teaching career, such as backwards planning and building connections, are directly applicable and incredibly valuable in starting and growing an online business.
• Adapting and pivoting business strategies are important for aligning with personal needs and ensuring a sustainable entrepreneurial journey.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

Tiffany Sattler shares her journey from teaching to entrepreneurship. She discusses the aspects of teaching that she loved, such as the "light bulb" moments when students finally understand a concept. She also talks about the challenges she faced in the education system, including a toxic work environment that affected her mental health. After experiencing a panic attack, she made the difficult decision to leave teaching and pursue a different path.

Tiffany discovered LinkedIn marketing and found her passion in helping others build their presence on the platform. She emphasizes the importance of mindset and consistency in entrepreneurship, as well as the need to give yourself grace and flexibility during the journey.

Key Takeaways:

• Teaching can be incredibly rewarding, especially when you witness those "light bulb" moments when students finally understand a concept.
• Mental health and well-being should be a priority, and it's okay to leave a toxic work environment for the sake of your own well-being.
• It's important to find a career or business that aligns with your values and allows you to continue learning and growing.
• Mindset and consistency are key in entrepreneurship. Visualize your success and show up consistently, even when you're not seeing immediate results.

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.