199 episodes

Hey driven woman entrepreneur! You love owning your own business, but staying focused, managing your mindset, and making all the decisions on your own can be a challenge. Join business strategist, mentor, coach, and former psychotherapist Diann Wingert, for your weekly dose of no-BS straight talk that cuts through the hype and false promises and delivers both insights and actionable advice every week. The Driven Woman Entrepreneur Podcast alternates between straight-shooting solo episodes, guest interviews with other successful female solopreneurs, and client success stories of women who have worked with Diann to transform their businesses and mindset. Diann works with established female solopreneurs: coaches, consultants, creatives, and independent professionals who are ready to lean into what truly makes them different so they can stand out from the crowd and create a profitable, sought-after solopreneur business. Her signature framework, The Boss Up Breakthrough, was designed to address the specific problems that hold us back once we are a few years into solopreneurship: struggling to ask for and get the price we want and the clients we want, clearly and confidently communicating what makes us different and creating the kind of boundaries that protect our time, energy and talent. Oh, and because this question gets asked a lot, Diann does work with clients of all genders, even though her marketing is directed toward women. Her website is https://www.diannwingertcoaching.com The podcast has an E rating, not because there is an excess of F-bombs in every episode (there aren’t) but because some listeners prefer to avoid learning from those who include colorful language in their self-expression. CAUTION: Regular consumption of this podcast is likely to be detrimental to your limiting beliefs and may result in the enlargement of your perspective, profits, and potential for success. If you are ready to go from driven but distracted to focused, fired up and flame retardant, you're in the right place. Check it out and decide for yourself!

The Driven Woman Entrepreneur Diann Wingert

    • Business
    • 5.0 • 80 Ratings

Hey driven woman entrepreneur! You love owning your own business, but staying focused, managing your mindset, and making all the decisions on your own can be a challenge. Join business strategist, mentor, coach, and former psychotherapist Diann Wingert, for your weekly dose of no-BS straight talk that cuts through the hype and false promises and delivers both insights and actionable advice every week. The Driven Woman Entrepreneur Podcast alternates between straight-shooting solo episodes, guest interviews with other successful female solopreneurs, and client success stories of women who have worked with Diann to transform their businesses and mindset. Diann works with established female solopreneurs: coaches, consultants, creatives, and independent professionals who are ready to lean into what truly makes them different so they can stand out from the crowd and create a profitable, sought-after solopreneur business. Her signature framework, The Boss Up Breakthrough, was designed to address the specific problems that hold us back once we are a few years into solopreneurship: struggling to ask for and get the price we want and the clients we want, clearly and confidently communicating what makes us different and creating the kind of boundaries that protect our time, energy and talent. Oh, and because this question gets asked a lot, Diann does work with clients of all genders, even though her marketing is directed toward women. Her website is https://www.diannwingertcoaching.com The podcast has an E rating, not because there is an excess of F-bombs in every episode (there aren’t) but because some listeners prefer to avoid learning from those who include colorful language in their self-expression. CAUTION: Regular consumption of this podcast is likely to be detrimental to your limiting beliefs and may result in the enlargement of your perspective, profits, and potential for success. If you are ready to go from driven but distracted to focused, fired up and flame retardant, you're in the right place. Check it out and decide for yourself!

    Making Business Finances Less Daunting and Less Lonely with Claudia Nerio

    Making Business Finances Less Daunting and Less Lonely with Claudia Nerio

    Most podcasts for female solopreneurs focus on the more fun aspects of being your own boss, like flexibility, creativity, and building a business based on passion and purpose. 
    Unfortunately, we really limit our success and sustainability if we neglect the “back end” of our business, the unsexy stuff like tax election, business finances, and accounting. 
    My guest today is Claudia Nerio, VP of People at Collective, for a lively conversation about the risks of ignoring or bootstrapping our business finances, and the rewards of delegating them to a team of experts, while becoming part of a vibrant solopreneur community.
    We talk about everything from our own experiences transitioning to working from home to client success stories and our mutual love of true crime podcasts.  
    🎙️Highlights of this conversation:
    Embracing delegation: Even as a solopreneur, recognize the power of focusing on your strengths. Delegating certain tasks frees up time for you to excel in your zone of genius.
    Solopreneurship & community: Combat the loneliness of going solo by joining a community like The Collective, which offers essential back-office support and a network of like-minded individuals.
    Business finance & tax Structure: Tapping into the collective wisdom and experience of experts at an affordable price means avoiding costly pitfalls and ensuring your solo venture thrives.

    Mic Drop Moment: 
    "The desire to venture out on your own and to be your own boss has always been there, right? Now I think with the rise of working from home has created businesses like Collective that have found a high demand space in the market to be able to make it easier for people to go out and be a business of one just and pursue their dream."
    — Claudia Nerio 

    Who would be a perfect fit for The Collective?
    Coaches, Consultants, Creatives, Independent ProfessionalsSingle member LLCs and one person businesses making $60-80K+ profit Want financial & legal services in one stop shopLooking for a community of like minded solopreneurs 
    Find out more:  https://www.collective.com/

    If you are a solopreneur who is ready to get off the struggle bus and love your business again, this might be the perfect time to work with me.
    My Boss Up Breakthrough framework has just been updated to put more emphasis on implementation, so we make sure you get, and stay in momentum. 

    I’ll help you Boss Up your boundaries, your offers, your pricing, and your marketing strategy and remove anything that keeps you a best-kept secret. 
    We will also make sure you are including mental wellness in your business plan so that you’re not just successful on the outside, but aligned with your values, and priorities on the inside.  
    Want to know more?  Schedule a free consultation here: https://bit.ly/3qrJ9YQ

    Not quite ready to work with me, but wonder what it would be like? Grab my private podcast,  “Show Up Like a Boss”. 
    It’s free, and you listen to it in the same podcast player where you hear this show. 
    It’s kind of like a backstage pass of 10 clips of me coaching and tips for how to apply the strategies to your own business and life.  Check it out:  https://bit.ly/3ZOD3CK

    • 44 min
    What's Holding You Back?

    What's Holding You Back?

    There are six common patterns of beliefs and behaviors that tend to hold female entrepreneurs back, particularly those with ADHD tendencies, and in this straight-talking solo episode, I am going to discuss what to watch for, why they happen and most importantly, what to do about it. 
    Some of us are lucky to just have one of them, but these patterns tend to travel in packs, so it's likely that you're dealing with a couple, several or even all of them.
    No matter how smart, strong, skillful, and savvy you are, these patterns are really really common and very effective at holding you back from the success you're striving for and deserve.
    If you are struggling with distractibility, perfectionism, procrastination, people-pleasing, impulsivity, or time blindness, it is harder to reach your entrepreneurial goals and fulfill your business’s potential. 
    This episode is full of insights gained from managing my own tendencies and from working with clients just like you.  
    And, before you listen, remember this: none of these obstacles will prevent you from being successful as an entrepreneur, but they do make things take longer and be more strenuous. So, let’s get them under control so you can have more success and a lot less stress. 
    Mic Drop Moment 🎙️
    "You do not need to be available and accessible at all times. We've been conditioned to think we always have to be responsive to others, but you can change your mindset on this."
    — Diann Wingert  
    Take the "What's Holding You Back" Quiz and get your customized series of emails designed to support your entrepreneurial journey. 
    Don't keep these insights all to yourself - Share this episode with someone who's ready to get out of her own way and fulfill her business dreams! 

    • 29 min
    Staying Small is Not Playing Small with Maggie Patterson

    Staying Small is Not Playing Small with Maggie Patterson

    Did you know that despite the pressure to scale and grow indefinitely, the majority of businesses are small, and that most female entrepreneurs do not reach six figures?
    We discuss this and much more in this eye-opening episode with BS-free business consultant, Maggie Patterson! 
    Maggie and I dig into the myths and hype that lead small business owners to invest in things that do not move the needle,  cause them unnecessary stress and anxiety and shrinking their bottom line. 
    If you are one of the many female solopreneurs who is questioning whether she wants to grow an online empire or simply stay small and sustainable, this episode is a must listen! 
    Key Takeaways from the Episode:
    🎙️ The importance of critical thinking and questioning in decision-making
    🎙️ Challenges of making hasty decisions in purchasing courses and other products
    🎙️ Marketing tactics and survivorship bias in the online business ecosystem
    🎙️ Impact of societal expectations on entrepreneurship and mental health
    🎙️ Distinguishing between mindset issues and reasonable concerns in business
    Mic Drop Moment: 
    "I want to create a community and environment where we can grapple with, 'How do I pay myself more? How do I sell strategy? How do I plan in a way that actually works for me?'"   Maggie Patterson

    Want more of Maggie?  
    The BS-free Service Business Podcast: https://apple.co/4bcJMwl
    Staying Solo Squad:https://bsfreebusiness.com/squad/
    Maggie on IG: https://www.instagram.com/bsfreebusiness/

    Also mentioned in this episode:  
    Duped Podcast - co hosted by Maggie & Michelle Mazur - https://duped.online/

    If you are a solopreneur who is ready to uncomplicate your business and maximize your purpose and profit, this is a perfect time to work with me.
    My Boss Up Breakthrough framework has just been updated to put more emphasis on implementation, so we make sure you get, and stay in momentum. 

    I’lll help you Boss Up your boundaries, your offers, your pricing, and your marketing strategy and remove anything that keeps you a best kept secret. 
    We will also make sure you are including mental wellness in your business plan so that you’re not just successful on the outside, but aligned with your values, and priorities on the inside.  

    Want to know more?  Schedule a free consultation here: https://bit.ly/3qrJ9YQ

    Not quite ready to work with me, but wonder what it would be like? Grab my private podcast,  “Show Up Like a Boss”. 
    It’s free, and you listen to it in the same podcast player where you hear this show.  It’s kind of like a backstage pass to working with me, includes 10 clips of me coaching and tips for how to apply the strategies to your own business and life.  Check it out:  https://bit.ly/3ZOD3CK

    If you found this episode insightful, please share it with someone who could benefit from a fresh perspective on entrepreneurship, mental well-being, and the pursuit of authentic success!

    • 44 min
    It's Time to Rebrand The Driven Woman Entrepreneur Podcast

    It's Time to Rebrand The Driven Woman Entrepreneur Podcast

    The Driven Woman Entrepreneur Podcast is coming up on 200 episodes, it is time for a rebrand and I need your help.
    In this behind-the-scenes solo episode, I share where I am in the process of rebranding the podcast, as well as how I recognized that it is time, and some helpful advice for avoiding boredom and staying consistent.
    If you're an aspiring or emerging podcaster, an entrepreneur, or a person with ADHD who tends to get stuck in the messy middle of long-term projects, this episode is for you!
    I've recently received some feedback that there might be a disconnect between what I'm talking about on the podcast and either the name of the podcast, the show art, the description, the categories, the episode titles, the guest interviews, or all of the above.  So, instead of being stubbornly self-sufficient and trying to figure it out on my own, I’m turning to you.
    In this episode, you'll hear:
    The importance of facing discomfort and making decisionsThe power of asking for feedback and not making assumptions.The journey of the podcast and how it has evolved over time.My personal experience with starting something new, overcoming challenges, and staying committed.
    Mic Drop Moment 🎙️
    "Isn't it perfectly obvious that the people I should be asking for help from to determine the future direction of the podcast are the ones who are actually listening to it?" 

    Thank you in advance for sharing your feedback with me! Here are your options:
    Google Form (Preferred)  https://bit.ly/47AFdJ3
    Email me: diann@diannwingertcoaching.com 
    Leave a voice message: https://bit.ly/3we0Kri  (90-second limit) 
    DM me on Linked In: https://www.linkedin.com/in/diannwingertcoaching/ or Instagram: https://www.instagram.com/coachdiannwingert/

    We're excited about the future, and we can't wait to hear from you!

    • 18 min
    Relationship Status with Social Media? "It's Complicated" with Andrea Jones

    Relationship Status with Social Media? "It's Complicated" with Andrea Jones

    The number of entrepreneurs talking about burnout, saying they have a love-hate relationship with social media or wishing they could just opt out altogether, but worry about possible negative consequences just keeps growing, but it’s undeniable that social media is a part of our lives, and the marketing of our small businesses. 
    I have certainly been struggling in my relationship with social media and so have a number of my female solopreneur clients, so I dedicated it was time to chat with an expert whose insights I value. 
    Today’s guest, Andrea Jones is a social media strategist who's been navigating the digital landscape for over a decade. Her perspective has evolved beyond the traditional focus on audience growth to prioritizing meaningful connections and community building.
    With a passion for creating genuine relationships, Andrea brings a unique perspective to this conversation about the role of social media in entrepreneurship.
    If you’re feeling the weight of a “complicated” relationship with social media, this episode is a must-listen.
    It’s time to reclaim our power and transform our social media presence into one that feels satisfying, sustainable, and aligned with our personal and professional values, and this thoughtful conversation just may help you take the first step. 
    Key Takeaways from the Episode:
    🎙️The difference between engagement and connection in social media, and why genuine connections cannot be manufactured.
    🎙️ How to navigate social media as a business owner by creating tangible, real, and response-style content that resonates with consumers.
    🎙️The negative impact of overexposure to social media and how to alleviate social media burnout by prioritizing non-scalable actions 
    🎙️The importance of recognizing your own goals and values, separate from the social media platform's goals.
    Mic Drop Moment: 
    “And, for me, personally, the things that bring me joy are not the ones that  I can scale.” Andrea Jones

    Mentioned by our guest in this episode:
    Travis Brown:  https://www.instagram.com/travisbrown/

    Want more of Andrea?  Here’s literally everything: https://onlinedrea.com/everything/

    If you are ready to transform your relationship with your business, from “complicated” to clarity, this is a perfect time to work with me through my Boss Up Breakthrough framework.  My framework has just been updated to put more emphasis on implementation, so we make sure you get, and stay in momentum. 

    I’lll help you Boss Up your boundaries, your offers, your pricing, and your marketing strategy and remove anything that keeps you a best kept secret.  We will also make sure you are including mental wellness in your business plan so that you’re not just successful on the outside, but aligned with your values, and priorities on the inside.  
    Want to know more?  Schedule a free consultation here: https://bit.ly/3qrJ9YQ

    Not quite ready to work with me, but wonder what it would be like? Grab my private podcast,  “Show Up Like a Boss”.  It’s free, and you listen to it in the same podcast player where you hear this show.  It’s kind of like a backstage pass to working with me, includes 10 clips of me coaching and tips for how to apply the strategies to your own business and life.  Check it out:  https://bit.ly/3ZOD3CK

    To put these insights to work in your relationship with social media, ask yourself this...

    • 52 min
    Incorporating Buddhist Wisdom for a More Mindful Business

    Incorporating Buddhist Wisdom for a More Mindful Business

    Drawing from my background as a cognitive behavioral psychotherapist who embraced the principles and practices of Buddhism about twenty years ago, in this rather personal solo episode, I share how mindfulness can be applied to business, emphasizing the importance of reducing unnecessary suffering and approaching business challenges with self-awareness and empathy. 
    Despite not fitting the stereotypical image of a Buddhist, I have found these practices absolutely transformational and decided to record and share this episode because I find that many people want to know more about it.  I have undergone a Buddhist ceremony and consider Buddhism my religion of record, I tend to view it more as a philosophy that influences the way I approach my life, relationships and business.  Maybe there is something in this ancient wisdom tradition for you too. 
    If you are Buddhism-curious, have heard about mindfulness practice or are just looking for ways to manage your well being and mental health, and lower the emotional stress load of solopreneurship, this episode offers insights into how to incorporate Buddhist principles into business, such as non-attachment, right action, and the neutral nature of money. 
    Throughout the episode, I’ll discuss the following key points:
    - Shifting our mindset about effort to feel more grace and ease in its flow in business and life
    - Managing emotions and thoughts when faced with disappointment or unwanted outcomes in business
    - Exploring the concepts of right action, non-attachment, and reducing unnecessary suffering in our work with others 
    - Embracing a mindful approach to business decisions and changing our perception of money as a tool

    Mic Drop Moment 🎙️
    “If I allow myself to get too focused on how fast someone else is growing, or how big their audience is, or how much more successful they appear to be with fewer years in business than me, I have brought upon myself a level of unnecessary suffering that does nothing for my well-being or my mental health, and it does nothing for my business."  Diann Wingert 

    Mentioned in this episode: 
    The Four Noble Truths: https://bit.ly/48QaNDT

    Make the decision now to start 2024 off right.  I have been revising my signature program, The Boss Up Breakthrough 🔥 to put more focus on implementation and accountability and can’t wait to start helping my clients get results even faster. 
    Let me help you right size your business,  avoid burnout, establish sustainable boundaries, and uncover the profit potential that is hidden because you have too many ideas, offers and ways to work with you.  If you have ADHD and/ or are gifted, I am your ideal mentor. 

    It’s hard to identify and implement what’s truly necessary on your own, so if you’ve been thinking about making changes for a while, let’s work together so you can actually move the needle.  At this time,  I am only accepting 1:1 clients and the first step is to schedule a free 30-minute consultation right here:  https://bit.ly/3qrJ9YQ 🌟


    If this episode has given you some insights and you are ready to take the first step toward implementing them,  won’t you share your “ah ha” moments with me?  Here are 3 ways to do so:

    Email me: diann@diannwingertcoaching.com 
    Voice message: https://bit.ly/3we0Kri
    DM me on Linked In: a href="https://www.linkedin.com/in/diannwingertcoaching/"...

    • 34 min

Customer Reviews

5.0 out of 5
80 Ratings

80 Ratings

ncramer34 ,

What an eye opener!

This episode with Nicole Kalil was so helpful for reframing my mindset around fully embracing ME and who I am authentically. Thank you for providing such value and hosting such wonderful guests Diann!

cassiejo2711 ,

So helpful and insightful!

Thank you for this show! The topics help me move through those stuck places and get back into my flow!

Jessie Bouton ,

Always makes me want to shut up and drive!

I love Diann’s candidness and tangible real life advice on how to get out of your own way and use your power (get in the drivers seat) to move forward towards goals.

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