113 episodes

Ready to take that leap of faith and finally chase those dreams of yours? It's not always easy to stay motivated when you're balancing a teaching career, family, and home life, but that's exactly what we're here to help you do. I'm your host, Dori Stewart, and this is the Teacher Turned Entrepreneur Podcast. Around here, we like to talk about our collective and sometimes crazy experiences as entrepreneurs, teachers, and women who do it all. If you've been looking for more in life than grading papers and conferences, this is for you!

I've been called the teacher turned entrepreneur. After spending 11 years in the classroom, I left to start a business that I grew into a multi-million dollar brand. It doesn’t matter where you’re currently at; having someone cheering you on makes a world of difference to get to the head of the class. I love that I can bring that to you here. If you’re ready to build the life you’ve been dreaming of, stay tuned as we dig deep into what it takes to turn teachers into true entrepreneurs!

Teacher Turned Entrepreneur Dori Stewart

    • Business
    • 5.0 • 71 Ratings

Ready to take that leap of faith and finally chase those dreams of yours? It's not always easy to stay motivated when you're balancing a teaching career, family, and home life, but that's exactly what we're here to help you do. I'm your host, Dori Stewart, and this is the Teacher Turned Entrepreneur Podcast. Around here, we like to talk about our collective and sometimes crazy experiences as entrepreneurs, teachers, and women who do it all. If you've been looking for more in life than grading papers and conferences, this is for you!

I've been called the teacher turned entrepreneur. After spending 11 years in the classroom, I left to start a business that I grew into a multi-million dollar brand. It doesn’t matter where you’re currently at; having someone cheering you on makes a world of difference to get to the head of the class. I love that I can bring that to you here. If you’re ready to build the life you’ve been dreaming of, stay tuned as we dig deep into what it takes to turn teachers into true entrepreneurs!

    #113: Best Advice for Aspiring Entrepreneurs? There’s No One Path, So Trust Your Instincts! with Kim Marsh

    #113: Best Advice for Aspiring Entrepreneurs? There’s No One Path, So Trust Your Instincts! with Kim Marsh

    For the gifted storyteller featured on this episode of Teacher Turned Entrepreneur, the doors to autonomy and empowerment opened with the launch of her Open Book Company. Part of the pandemic-inspired Great Registration, Kim Marsh had had enough of applying for (and not getting) writing jobs. So she created her own, launching a freelance business that showcases her communications skills and the broad base of knowledge she accumulated working in the nonprofit education and corporate sector. She has found the perfect niche: “So many people are so busy doing their thing and having amazing impact that they don’t necessarily have the time to write about it and tell others.” That’s where Kim comes in! Both as an author and a coach, she’s open to every kind of writing assignment, from memoirs to blog posts to corporate bios.
    In addition to ghostwriting, Kim also hosts writing circles and offers one-to-one coaching for aspiring authors and entrepreneurs. Wedding vows. Podcast scripts. Social media snippets. It doesn’t matter. Kim creates space, accountability and encouragement – no matter what you’re working on. Running her own show wasn’t born of an entrepreneurial dream so much as Kim’s decision to embrace what the universe was offering – an invitation to freedom! All the rejections from would-be employers were overwhelming and disheartening at the time, but today Kim clearly sees that she would never have uncovered a calling or started the independent business she loves had she not run into obstacles and dead ends. What “no” is out there, waiting for YOU to come up with a way to say, “Yes”?!
    Here are key takeaways from the conversation:
    • Do you love telling stories? Communications might be your thing and in the Age of Information there’s lots of need for content!
    • Applying for jobs. Lack of control. The rejections. Waiting for the gold star. An independent business can mean saying goodbye to all of the above!
    • Living our dreams doesn’t always start with … a dream. Sometimes the thing we don’t even know we want is born of necessity and the obstacles that shape our path.
    • Have a book inside you but can’t seem to get started? Writing circles are a great way to find a supportive community to help motivate you and prioritize your project.
    • Accountability can be a powerful motivator. It’s a tool to help you show up for yourself and progress (while also showing up for others).
    • If you’ve got negative voices in your head, don’t let them discourage you. All writers experience self-doubt. It’s normal! Just keep on going!
    • When it comes to satisfaction and success (in business and in life), there’s a very strong correlation with authenticity and listening to your own instincts!
    Are you ready to find your true calling and walk away from your teaching job once and for all?
    It is your time to get a solid grasp on the potential opportunities available to you so you can get started on your entrepreneurial journey and change your life!
    Download your copy of this free, valuable PDF resource and access 20 different descriptive business ideas that are perfect for a teacher turning entrepreneur.
    The Teacher’s Guide to Finding Your Perfect Business Idea (without going back to college)

    • 27 min
    #112: Attention Busy Entrepreneurs: Meditation Can Cut Through All the Noise and Distraction! with Saskia Seeling

    #112: Attention Busy Entrepreneurs: Meditation Can Cut Through All the Noise and Distraction! with Saskia Seeling

    Do you know your own mind? That’s a literal question this guest. Saskia Seeling left her native Germany in search of her truest self and found along the way inspiring meditation tools for transformation, especially when it comes to taming overwhelm. Today she brings to the women she coaches a whole new approach to mindset, vision and action. By nurturing the “self” through radical self-love, Saskia invites the fullest expression of feminine power – the most powerful of entrepreneurial fuel!

    You’ll learn on this episode about the way in which Saskia supports her clients and techniques we can all use to unlock empowerment. It starts with quieting the noise – no small feat in a world of online chatter, constant deadlines, family obligation and social expectation. For Saskia the journey started with finally understanding (and embracing) a basic fact: She’s not perfect. She’ll never be perfect. And that’s perfectly okay! So if you’re feeling overwhelmed, consider carving out space for a female-oriented business mentor with a plan. Saskia’s actionable tips and deep knowledge of meditation will steady and energize you, whatever the journey ahead!

    Here are key takeaways from the conversation:
    • Many (maybe most!) entrepreneurs do not follow a straight trajectory. It’s a process of self-discovery and clarity.
    • Unknowns are okay! Stay tuned into yourself and signs will emerge and point the way!
    • Are you listening for feedback? Other people can help you figure out what you need to know and what opportunities await!
    • It’s okay to start small. You needn’t uncover your life’s purpose in one go!
    • Check in with your nervous system. Is it in survival mode? Fight or Flight! Meditation is a great way to bring your body back into alignment.
    • Hearing lots of chatter in your head? That’s okay. Acknowledge it and then get quiet inside your body.
    • Taking action is the first step towards identifying purpose. Even when you’re not sure where the next step will lead!
    Are you ready to find your true calling and walk away from your teaching job once and for all?
    It is your time to get a solid grasp on the potential opportunities available to you so you can get started on your entrepreneurial journey and change your life!
    Download your copy of this free, valuable PDF resource and access 20 different descriptive business ideas that are perfect for a teacher turning entrepreneur.
    The Teacher’s Guide to Finding Your Perfect Business Idea (without going back to college)

    • 20 min
    #111: Go Ahead. Get in the Driver’s Seat, Even If Your Life Path Isn’t Entirely Clear! with Sophia LePage

    #111: Go Ahead. Get in the Driver’s Seat, Even If Your Life Path Isn’t Entirely Clear! with Sophia LePage

    Burned out, her marriage in tatters, Sophia LePage had to decide: Was she going to commit to her soul or continue to follow society’s lead? It took courage but ultimately it felt like there was no choice but for Sophia to definitively break with what had been an inauthentic life path. Departing London to study yoga, shamanism and Feminine Embodiment, Sophia uncovered her truest nature and a calling that had been there all along. Today she is dedicated to helping other women – especially those who, like her, have perfectionistic tendencies – to realign with their truest selves.

    Sophia reflects on common stumbling blocks faced by highly competent women as well as the techniques she deploys to help clients reconnect with their bodies and stay centered in their hearts. She also offers advice to women on the brink of change. Whether you’re feeling the tug to travel to a foreign land or simply to get quiet in the comfort of your own home, Sophia urges all of us to be brave, claim our innate femininity and embrace our unique perspectives. Your entrepreneurial – and personal – journey starts with a simple question, says Sophia: “What’s the best, most aligned way to get right with – and truly live for – yourself?”

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!

    Here are key takeaways from the conversation:
    • Living your truth means pausing to ask: What does my soul truly want for me?
    • For many, travel offers clarity and opportunity when we’ve lost our way.
    • When it feels like your life doesn’t make sense, try connecting the dots. You may have picked up valuable skills and insights along the way without fully realizing it!
    • Are you perfectionistic? An overachiever? Ask yourself: Are you doing it for someone else or yourself?
    • Entrepreneurial growth occurs when we break the “shoulds” and stop chasing validation.
    • Your menstrual cycle is real. Ignoring the body’s rhythm and need for rest at certain times of the month can impede productivity and pleasure overall.
    • Change is a gradual process. Step #2 will become clear after you’ve taken step #1.

    Are you ready to find your true calling and walk away from your teaching job once and for all?
    It is your time to get a solid grasp on the potential opportunities available to you so you can get started on your entrepreneurial journey and change your life!
    Download your copy of this free, valuable PDF resource and access 20 different descriptive business ideas that are perfect for a teacher turning entrepreneur.
    The Teacher’s Guide to Finding Your Perfect Business Idea (without going back to college)

    • 20 min
    #110: Two Successful Online Businesses? This Mompreneur Figured It Out On the Job! with Krystal Booker

    #110: Two Successful Online Businesses? This Mompreneur Figured It Out On the Job! with Krystal Booker

    For businesses seeking operational efficiency and clarity, there’s probably no better resource than KrystalClear Virtual – the brainchild of a young mom who wanted to take control of her schedule by working online. Together with her team, Krystal Booker brings overwhelmed business owners order out of chaos – virtually! Her agency offers a range of practical support to help offload tasks as simple as answering phones or as complex as designing ongoing social media strategy and implementation. The result? Increased productivity, scalability and – most of all – the peace of mind that allows even the busiest of entrepreneurs to focus on what they do best.

    How did Krystal get started? Well, there was no master plan. As she explains on this episode of Teacher Turned Entrepreneur, she simply sat down and considered the skills she had acquired as a dental assistant, a mom and elsewhere through the course of her life. She looked for opportunities to educate herself and was willing to start small. Most of all, she wasn’t shy about looking for help. “There’s power in your network. There’s power in the ask,” says this creative, busy Mompreneur. “Go out there and make yourself known. Show up in ways that you feel confident in showing up and you’re going to find the clients that are meant to work with you!” And if you’ve already launched your venture and feel swamped? Consider this: A virtual assistant can automate systems, save you time and prevent costly mistakes!

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!


    Here are key takeaways from the conversation:
    • Want control of your life and schedule? Entrepreneurialism is mom-friendly!
    • CEOs often don’t really know what’s missing or in what areas they could most use help.
    • Get to the Root: If you want to save time and money, dig deep to find the bottlenecks.
    • In order to get to your big picture, consider getting help from someone able to detach.
    • Consult with an automation expert sooner than later. It minimizes human error and unnecessary expense in the long run.
    • You are time. You are money. Operations support frees you to focus on your core mission.
    • Interested in becoming a VA? Sit down and list out your skill sets as a start!
    • Wondering how to generate client interest? Leads are as close as your own contact list. But you have to be willing to put the word out there and ask for help!
    Are you ready to find your true calling and walk away from your teaching job once and for all?
    It is your time to get a solid grasp on the potential opportunities available to you so you can get started on your entrepreneurial journey and change your life!
    Download your copy of this free, valuable PDF resource and access 20 different descriptive business ideas that are perfect for a teacher turning entrepreneur.
    The Teacher’s Guide to Finding Your Perfect Business Idea (without going back to college)

    • 20 min
    #109: Coach to the Coaches: This Entrepreneur Unpacks the Wisdom that Resides Within with Taryn Watts

    #109: Coach to the Coaches: This Entrepreneur Unpacks the Wisdom that Resides Within with Taryn Watts

    Coaching has exploded in popularity over recent years, but what is it that makes the best of them stand out from the pack? This guest eloquently cuts to the core mission at the heart of the most effective coaching: Holding space. “It’s not something you do,” says Taryn Watts, a life coach whose training methodology is inspiring a generation of coaches. “It’s something you become.” Her Mind Rebel™ Academy offers a framework to unlock self-awareness and establish the clarity required to minimize projections and other coaching pitfalls.

    One of many things that sets Mind Rebel™ apart is its seal of approval from the International Coaching Federation. Taryn has brought an entrepreneurial skill set to the very interior, sacred work of helping her students dig deep – so that they can go on to coach others who wish to do the same. “As a coach you’re only as willing to go in deep with another as you are willing to go in deep with yourself,” says Taryn. One small step after another, she has built a thriving platform in service of others – which has always been her primary calling. Learn about Taryn’s unique training program methodology as well as some common misconceptions about what it means to be a life coach. At its heart, says this mom of two, the work is about opening up room for clients to uncover what resides within us all: Inner wisdom and compassion.

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!


    Here are key takeaways from the conversation:
    • Going from 9-to-5 doesn’t have to happen overnight. Remember: Baby steps work!
    • Do you need a plan? Clarity usually starts with an “aha” about your passion or priorities.
    • Focus like a laser on each opportunity to serve and the momentum (additional clients, more $$) will follow!
    • If there is a drumbeat in your life – something people are asking for because of a skill you possess – maybe it’s time to figure out whether it’s your calling.
    • The magic of coaching? It creates dedicated spaces that enables people to unpack issues and look within for answers.
    • The truest, most integrity-filled joy comes from a quiet place deep within that we have to uncover for ourselves (And of course support from a coach always helps!).
    • One of the gifts of becoming a coach is a commitment to living the examined life. It’s not always easy, but it’s incredibly rewarding.
    • Want to distinguish yourself? Keep your eyes in your own lane! It doesn’t matter who else is out there or where you stand. Just focus on your individual passion and practice.
    • Accreditation Matters: Coaching has exploded and isn’t currently regulated, which is why it’s good to look for people with credentials from bodies like the International Coaching Federation (ICF).
    • You don’t have to figure it all out. Entrepreneurial journeys start with that first step. Then another!

    Are you ready to find your true calling and walk away from your teaching job once and for all?
    It is your time to get a solid grasp on the potential opportunities available to you so you can get started on your entrepreneurial journey and change your life!
    Download your copy of this free, valuable PDF resource and access 20 different descriptive business ideas that are perfect for a teacher turning entrepreneur.
    The Teacher’s Guide to Finding Your Perfect Business Idea (without going back to college)

    • 28 min
    #108: This Online Business Manager Quit Her 9-to-5 to Help Entrepreneurs Take Flight! with Arijana Libasic

    #108: This Online Business Manager Quit Her 9-to-5 to Help Entrepreneurs Take Flight! with Arijana Libasic

    We’ve all had them – those days when it seems like we’re running in circles, trying to drive business while doing endless tasks again and again. On this episode of Teacher Turned Entrepreneur you’ll learn about the powerful ways in which an online manager and other support systems can optimize your world. Arijana Ilibasic, founder of Scale & Simplify, is giving us all kinds of tips for identifying tasks we’re doing repeatedly and automating them with systems you might have no idea exists. She shares important advice for harried entrepreneurs trying to figure out whether they need to delegate and, if so, to what kind of assistant or other resource.

    We’re most able to scale efficiently when we’ve got processes and support systems in place but, warns Arijana, it’s all about ensuring the right fit. She’s got a list of important elements to consider before choosing a partner and she urges us to take our time! This is about finding the right fit based on a clear understanding of our strengths, skills and what we enjoy. From there the goal is to outsource things that are labor-intensive and time-consuming. You’ll enjoy hearing the excitement Arijana feels about having found this niche and all the great tools available for entrepreneurs. Want to free yourself up to focus on clients and revenue generation? Here’s a great place to start!

    Ready for the Arijana’s free Ultimate Delegation Cheatsheet? You can find out what to outsource and to whom by downloading this and other handy resources here.

    If you enjoyed this episode of Teacher Turned Entrepreneur, click here to hear past shows and leave comments!

    Here are key takeaways from the conversation:
    • It’s not where you start out but the clues you uncover along the way. You’re not alone if you didn’t have a dream job growing up or even right out of school. Trial and error works!
    • Are you a coach (or independent business owner of some other kind) juggling too many things? There’s a reason that online and virtual managers have flourished, especially since pandemic.
    • Time trackers like Clockify and Toggl are a great tool for figuring out what tasks are most time-consuming and labor-intensive.
    • Check out an app like Zapier (which you can get started with for free) to automate things like spreadsheets, documents, surveys and marketing/communications apps.
    • Before hiring an online assistant or other outsourced team member, take stock of the traits and abilities that will make a good match. You’re looking for a partner – not a pal!
    Are you ready to find your true calling and walk away from your teaching job once and for all?
    It is your time to get a solid grasp on the potential opportunities available to you so you can get started on your entrepreneurial journey and change your life!
    Download your copy of this free, valuable PDF resource and access 20 different descriptive business ideas that are perfect for a teacher turning entrepreneur.
    The Teacher’s Guide to Finding Your Perfect Business Idea (without going back to college)

    • 21 min

Customer Reviews

5.0 out of 5
71 Ratings

71 Ratings

Kelley Tyan ,

Excellent and hopeful!

I love how Dori makes us feel as if we can conquer the world by taking small action steps. She gives us so many strategies and tips to encourage us to just go for it! She is helping me to never stop dreaming and go big or go home!

OrganizerJanet ,

Can't want for the next 100 episodes!

Inspirational for everyone not only teachers!!!

Podcast Ep.306 ,

So Moving!

Dori is a fabulous podcast host! I loved her most recent guest episode with Brittany Dixon. I can’t wait to listen to more podcasts in the future!

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