145 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 business and mindset. Some of our past guests have been non-sleazy sales maven Annie P Ruggles (# 86); The Tik Tok Teacher, Helen Polise (# 114); systems & scaling genius, Crista Grasso ( # 88); burnout expert Cait Donovan (# 52); rebel business coach Erika Tebbens (#64); event planner & productivity genie, Angela Proffitt ( # 54); money mindset coach Dr. Amanda Barrientez ( # 96); and author, speaker, and financial literacy coach, Melanie Lockert (#78). Some of our most frequently downloaded solo episodes are those on mindset, where Diann’s background as a therapist, coach, and fellow solopreneur really shines. Here are a few listener favorites: The Confidence Habit (# 71)The Cure for Imposter Syndrome (# 121) Negative Self Talk ( # 77) Your Zone of Genius ( # 67) Obligation Management (# 97) 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 System, 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 Driven Woman Entrepreneur Podcast exists for three reasons: Diann loves to share what she has learned and feels more authentic speaking than writing. She loves knowing that this podcast reaches and teaches female solopreneurs all over the world, to help them with their business, at no cost to them. The Driven Woman Entrepreneur Podcast was also created for those who know they need help to take their business beyond its current level of success by giving them access to Diann’s perspective and personality before hiring her. 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!

The Driven Woman Entrepreneur Diann Wingert

    • Business
    • 4.9 • 72 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 business and mindset. Some of our past guests have been non-sleazy sales maven Annie P Ruggles (# 86); The Tik Tok Teacher, Helen Polise (# 114); systems & scaling genius, Crista Grasso ( # 88); burnout expert Cait Donovan (# 52); rebel business coach Erika Tebbens (#64); event planner & productivity genie, Angela Proffitt ( # 54); money mindset coach Dr. Amanda Barrientez ( # 96); and author, speaker, and financial literacy coach, Melanie Lockert (#78). Some of our most frequently downloaded solo episodes are those on mindset, where Diann’s background as a therapist, coach, and fellow solopreneur really shines. Here are a few listener favorites: The Confidence Habit (# 71)The Cure for Imposter Syndrome (# 121) Negative Self Talk ( # 77) Your Zone of Genius ( # 67) Obligation Management (# 97) 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 System, 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 Driven Woman Entrepreneur Podcast exists for three reasons: Diann loves to share what she has learned and feels more authentic speaking than writing. She loves knowing that this podcast reaches and teaches female solopreneurs all over the world, to help them with their business, at no cost to them. The Driven Woman Entrepreneur Podcast was also created for those who know they need help to take their business beyond its current level of success by giving them access to Diann’s perspective and personality before hiring her. 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!

    Owning Who You're Not & Fully Embracing Yourself: Unpacking Nicole Kalil's Confidence Journey

    Owning Who You're Not & Fully Embracing Yourself: Unpacking Nicole Kalil's Confidence Journey

    Nicole Kalil shares her story of birthing her book, exposing the ironies of achieving success through a masculine lens and the personal journey of overcoming false confidence to ultimately become more trusting of herself.
    "I can't tell you how much of the confidence builders were required and necessary to write this book and to put it out there, and how much of the confidence derailers came up on a very regular basis. When we were editing, perfectionism was all over the place.  Pure head trash, like "will people even like this book." 

    Nicole Kalil is an author, speaker, and leadership coach who has dedicated her work to helping women build their confidence and reach their full potential. She is the author of the book "Validation is for Parking" which explores the journey of self-discovery and embraces the unique gifts and talents of each individual.

    We talked about how Nicole had a dream of writing a book for years but allowed fear to hold her back. Eventually, she realized her reasons were just excuses and took the leap. She eventually learned to trust herself, overcome the false messages of society and recognize her unique abilities while understanding that her worth lies beyond her physical appearance and pursuing success through the masculine lens. 

    In this episode, you will learn the following:
    1. What is the difference between confidence in men and women?
    2. What is the 'confidence con' and how does it hinder women?
    3. How can we raise confident humans in a world full of mixed messaging?

    Resources mentioned in this conversation:
    Elyse Archer’s Podcast “She Sells”: https://elysearcher.com/podcast/
    Jill Savage’s books on perfectionism: https://nomoreperfect.jillsavage.org/


    Want to connect with Nicole?:
    Get Nicole's Book "Validation is for Parking": https://nicolekalil.com/book
    Listen to her podcast: https://nicolekalil.com/podcast
    Check out her website: https://nicolekalil.com/

    Other episodes you'll enjoy:
    Episode #80 The Not-so-Secret Secret of Confidence with Nicole Kalil - http://bit.ly/40bNpNt
    Episode #126 Creating Confidence Through Personal Styling with Scarlett de Bease -  http://bit.ly/3XN5j7y
    Episode #114 Becoming Confident on Video with Helen Polise - https://bit.ly/3Io2HWU

    Connect with me: 
    LinkedIn: https://www.linkedin.com/in/diannwingertcoaching/
    Website: https://www.diannwingertcoaching.com/
    YouTube: https://www.youtube.com/channel/UC5qFHTPZTAxtYvVLyip3h0A

    Loved this episode? Leave us a review and rating here: a href="https://the-driven-woman-entrep.captivate.fm/review" rel="noopener noreferrer"...

    • 51 min
    What to Expect During a Free Consultation

    What to Expect During a Free Consultation

    One of the practices in the coaching industry that I really dislike is the Discovery Call.  It sounds harmless, but most coaches have been trained to use manipulative tactics to "close leads" on these calls because what they don't tell you is that the purpose of the discovery call is for you to discover that you are in trouble and that coach is your solution.  Period. 
    A free consultation is a way for potential clients to discover if the coach is the right fit for them and for the coach to determine if the client is adequately prepared to have a successful coaching outcome. It is different from a discovery call because it focuses on the client's needs, rather than the coach's agenda. I use a free consultation very intentionally.  I first started doing so as a licensed psychotherapist in private practice in my former career and incorporated it into my practices as a coach. 
    I will not pressure the consultee to become a client, and I will not promise anything that I cannot deliver. I will provide guidance and advice, even if we are not a fit, and I will provide referrals to someone else if need be. I am taking on two more one-on-one clients, so if you are interested, don't wait and book your free consultation now.  The link to do so is right here in the show notes, below. 
    "Applied knowledge is power."
    In this episode, you will learn the following:
    1. What are the hard-hitting tactics used by coaches to convert leads into sales?
    2. What is the difference between a discovery call and a free consultation?
    3. How can applied knowledge, rather than just knowledge, be used to move the needle in your business or life?

    Book a free consultation with me:
    https://bit.ly/3qrJ9YQ

    Loved this Episode?  Here are a few others you'll enjoy:
    Episode #141: Stop Getting Ready & Take Action Now - http://bit.ly/3XCQ2Gs
    Episode #139: How to Know if You're Coachable - https://bit.ly/3Q9H7cv
    Episode #129: There is No Magic Pill - https://bit.ly/3TgUSH7

    Connect with me: 
    LinkedIn: https://www.linkedin.com/in/diannwingertcoaching/
    Website: https://www.diannwingertcoaching.com/

    Loved this episode? Leave us a review and rating here: 
    https://kite.link/https-www-diannwingertcoaching-com-podcast

    Chapter Summaries:
    [00:00:01]
    The purpose of a discovery call is to help potential clients discover that they need help in reaching their goals. Most coaches who sell high-ticket programs are not successful at ensuring that you, the potential client, get value for what you've invested. Many business owners are choosing to struggle rather than risk hiring another coach that doesn't actually help them move forward in their business.
    [00:04:21]
    Business owners are choosing to struggle and suffer on their own rather than risk hiring help. What is the difference between a discovery call and a free consultation? Applied knowledge is power. Learning without action is never going to move the needle in your business or life.
    [00:11:18]
    If you decide to schedule a...

    • 17 min
    Transforming Your Identity by Writing a Best Selling Book with Kim O'Hara

    Transforming Your Identity by Writing a Best Selling Book with Kim O'Hara

    Today's guest, Kim O'Hara was a Hollywood movie producer and screenwriter before transitioning to book coaching over 8 years ago.  Kim believes that everyone can write a book and that they often discover more about themselves through writing. Writing a book is much different than other forms of communication as it requires a transformation of identity and letting go of preconceived notions about ourselves and the book we are meant to write. Kim works with experts and thought leaders to help them write their books and believes that the process can lead to a great sense of both discovery and visibility.
    In this episode, you will learn the following:
    1. The transformation Kim went through from movie producing and screenwriting to book coaching 
    2. What is the divide between people who say they want to write a book and those who actually do?
    3. How does writing a book require a transformation of identity?

    Mic Drop Moment: 
    "Letting go of what you thought your book should be about is one of the greatest gifts you can give a reader." - Kim O'Hara

    Want to connect with our amazing guest, book coach Kim O'Hara?
    Website: https://www.kimohara.com/
    Podcast: https://www.kimohara.com/podcasts
    Book coaching services: https://www.kimohara.com/reach-out

    Mentioned in this episode:
    Episode #129  There is No Magic Pill - https://bit.ly/3TgUSH7 

    Kim’s client, divorce coach Kristen Noel https://www.kristennoel.com/best-self/

    Other episodes you will enjoy:
    Episode #115  What is Your Unfair Advantage? - https://bit.ly/3Pvhvpa
    Episode #71 The Confidence Habit - https://bit.ly/3LmDFY9

    Is this the year you commit to eliminating the obstacles in your business that are holding you back?  
     
    I have a few spots open NOW to work with me 1:1 through the 12-week Boss Up Breakthrough framework.  The first step is scheduling a free, 30-minute goodness-of-fit call by clicking here:  https://bit.ly/3qrJ9YQ
     

    Connect with me: 
    LinkedIn: https://www.linkedin.com/in/diannwingertcoaching/
    Website: https://www.diannwingertcoaching.com/
     
    Loved this episode? Leave us a review and rating here: 
    https://kite.link/https-www-diannwingertcoaching-com-podcast
     

    Chapter Summaries:
    [00:00:01]
    Kim O'Hara is a book coach to bestsellers who help high achievers write excellent books. I'm steeped in creativity all day long. This isn't your first rodeo, as they say.
    [00:00:46]
    When she moved into book coaching, the biggest transition was from fiction to nonfiction. She had gone from filmmaking through a

    • 43 min
    Stop Getting Ready & Start Taking Action

    Stop Getting Ready & Start Taking Action

    This episode is all about a lesson I learned the hard way in my own business and want to help you learn it quicker: Taking Action vs. Getting Ready.  What I learned is that getting ready doesn't move the needle and that there is no participation trophy in business. I learned to trust my instincts and to have specific benchmarks to know when enough preparation and planning are enough.  We also need to be leaders to our clients and team by taking action, not just focusing on our mindset. Furthermore, we need to stop overdelivering and undercharging and be mindful of not getting lost in researching and overcomplicating our ideas. 
    "There is no participation trophy or attendance award in business. It just doesn't matter.  Women business owners are first and foremost women. And because we're women, we have all been culturally conditioned to think that we're not enough. This belief can make you stuck in an endless cycle of getting ready instead of pulling the trigger. "

    In this episode, you will learn the following:
    1. How can women stop getting ready and start taking action in their businesses?
    2. What are the signs to look out for that you are spending too much time getting ready instead of taking action?
    3. What techniques can be used to overcome the cultural conditioning of not feeling enough and start trusting yourself and leading?

    Other episodes on this topic: 
    Episode #121 - The Cure for Imposter Syndrome https://bit.ly/3AnPBWe
    Episode #123 - Does Your Business Need You to Boss Up? https://bit.ly/3x9TInQ
    Episode #103 - How to Deal with Fear, Uncertainty & Doubt https://bit.ly/3Mp4sDZ

    Is this the year you commit to eliminating the obstacles in your business that are holding you back?  
    I have a few spots open NOW to work with me 1:1 through the 12-week Boss Up Breakthrough framework.  The first step is scheduling a free, 30-minute goodness-of-fit call by clicking here:  https://bit.ly/3qrJ9YQ
     
    Connect with me: 
    LinkedIn: https://www.linkedin.com/in/diannwingertcoaching/
    Website: https://www.diannwingertcoaching.com/
     
    Loved this episode? Leave us a review and rating here: 
    https://kite.link/https-www-diannwingertcoaching-com-podcast

    Chapter Summaries:
    [00:00:02]
    Stop Getting Ready and Start Taking Action is a hard-hitting, no-BSing solo episode. Most of the people that I work with as a consultant, coach, and business strategist are not beginners. You might be surprised how many people with years, even decades of experience can still get caught up in this trap.
    [00:01:34]
    Women business owners are first and foremost women. There is no participation trophy or attendance award in business. You need just enough planning to get you into action.
    [00:09:07]
    Early-stage solopreneurs get caught up in spending an inordinate amount of time choosing their logo, fonts, and brand colors, and creating their brand board. If you're consuming too much information and not taking action with it, that's a sign in general, being...

    • 36 min
    Uncovering the Bottleneck in Your Business with Amber de la Garza

    Uncovering the Bottleneck in Your Business with Amber de la Garza

    The story of how Amber de la Garza came to be a guest on this podcast is not the typical one.  It started over 3 years ago at Podcast Movement 2019.  I was a listener to her popular productivity podcast, Productivity Straight Talk, and recognized her at the conference.  Even though I did not have a podcast at the time, I approached her, introduced myself, and pitched her on the spot.   
    Amber has branded herself 'The Productivity Specialist", so you know she is intentional with her time.  She graciously accepted my pitch, on this condition: "Launch your podcast, get to 100 episodes, and then, I will be your guest."   Well, I've never been one to shy away from a challenge from someone I respect, so this interview, in episode #140, is the fulfillment of Amber's promise.  It's also a great lesson for those who need challenge and accountability to kick their motivation into gear. 
    Amber De La Garza is a sought-after speaker, trainer, writer, coach, and creator of The Leverage Lab, who helps entrepreneurs and small business owners learn to manage their time and build effective business systems.  She is the host of the Productivity Straight Talk podcast, wife, mom, dog mom, and calls Las Vegas home. 
    "The skill set of learning to invest your most precious resource, which is time, was incredibly valuable. The idea and identity of The Productivity Specialist was born."
     
    In this episode, Amber shares how her past career and life-changing events led her to focus on helping small business owners with their productivity, which leads to the concept of being the bottleneck in one's business, why it can be difficult to recognize, and why it tends to be a recurring pattern. 
     
    You will learn the following:
    1. What is the skill set of learning to invest your most precious resource, time?
    2. What would happen if a business owner becomes the bottleneck in their business?
    3. What life lessons can be gleaned from making difficult decisions about how to manage time and invest in team members?
     
    How to connect with Amber:
    Website: https://amberdelagarza.com/
    Podcast: https://amberdelagarza.com/podcast/
    Linked In: https://www.linkedin.com/in/amberdelagarza/
    Free time management mini-training: https://amberdelagarza.com/training/tbyt/
     
    Other episodes on productivity & getting out of your own way in your business: 
    Episode #137 The Hidden Reasons You Aren't Reaching Your Goals - https://bit.ly/3HuTsG5 
    Episode # 99 How to Create a Distraction-Free Business - https://bit.ly/36gQmW9
    Episode # 85 Setting Boundaries Like a Boss - https://bit.ly/3e3rCAR
     
    Is this the year you commit to eliminating the obstacles in your business that are holding you back?  
    I have a few spots open NOW to work with me 1:1 through the 12-week Boss Up Breakthrough framework.  The first step is scheduling a free, 30-minute goodness-of-fit call by clicking here:  https://bit.ly/3qrJ9YQ
     
    Connect with...

    • 54 min
    How to Know If You're Coachable

    How to Know If You're Coachable

    The beginning of a new year tends to be a time when business owners think about hiring a coach to help them move their business forward. At such times, most people focus on the credentials and credibility of the coach they are thinking about hiring, but in this episode, I share something even more important than that, determining whether you are even coachable.  
    This episode is about coachability: how to determine if you are ready for a coach and if hiring a coach would be beneficial for you.  In my own entrepreneurial journey, I learned that being coachable is not a set-and-forget situation, but changes over time and can depend on the circumstances.  
    We will dive into the three categories of coachability using my system -red light, yellow light, and green light - so you can make a truly informed decision on whether to hire a coach. Want to unlock the key to a successful coaching outcome?  Find out if you are coachable now and learn how to become more coachable if you’re not. 
    "Don't fall for the magical thinking that you're going to get great results simply because you hired a coach with a hefty price tag. You get the results based on coachability, the goodness of fit, and taking action. "
    In this episode, you will learn the following:
    1. What is coachability and how do you know if you are coachable?
    2. What are red light, yellow light, and green light indicators to determine if someone is coachable?
    3. What are the steps to becoming more coachable?
    Other episodes you'll enjoy:
    Episode #135 -  “Business Coach, Consultant or Strategist: Who Do You Need?”  https://bit.ly/3ivH3az
    Episode # 113 -  “Using an Application Process to Find Your Ideal Clients” https://bit.ly/3nsBM2A
    My Guest Interview on The Small Business Podcast: “Don’t Hire a Coach Until You Do This”:  https://apple.co/3MIEhJM
    Additional Resources mentioned in this episode:
    Mindset by Carol Dweck: https://amzn.to/3hOz34t
     
    Connect with me: 
    LinkedIn: https://www.linkedin.com/in/diannwingertcoaching/
    Website: https://www.diannwingertcoaching.com/
     
    Loved this episode? Leave us a review and rating here: 
    Apple: https://apple.co/2BZDFzc
    Android: https://www.podchaser.com/podcasts/the-driven-woman-1194485
     
    You already know you can only learn so much from a podcast, no matter how generously the host shares their wisdom.  Just imagine how different your business could look in 2023 can look if you get started right away.  I work with a limited number of clients at a time, so if you’re ready, don’t delay. 
    If you are ready for a hybrid strategist + coach, like my approach, and think we might be a fit,  there’s a link in the show notes to book your free consultation.  
    a href="https://calendly.com/diannwingert/free-consultation" rel="noopener noreferrer"...

    • 39 min

Customer Reviews

4.9 out of 5
72 Ratings

72 Ratings

Book Coach Kim ,

We always have room for improvement!

As a woman who has her hands in lots of buckets, I need to step back and evaluate my progress and how I feel about where I am at in my evolution. Diann gets to the point quickly and is empathetic because she had been where she advises! I highly suggest if you want to be smart in your day to day you make the time to listen to her podcast.

Niikki Burla ,

Do yourself a favor and subscribe

Love this podcast. A must listen for women!

Neenaperez ,

Fantastic Real Content!

Diann does a fantastic job with this podcast! I am totally a fan and looking forward to listening to the episodes from before and those that are coming in the future! You’re a truth teller, a straight talker with no sugar added and I freaking love it! ~Neena Perez

Top Podcasts In Business

Freakonomics Network & Zachary Crockett
Erika Kullberg
Ramsey Network
NPR
Jocko DEFCOR Network
Guy Raz | Wondery

You Might Also Like

Tracy Otsuka
Kate Moryoussef
David A Greenwood
Kristen Carder
Katy Weber
ADDitude