Daring Breakthroughs with Jenn Landis

Jennifer (Jenn) Landis
  • 5.0 (2)
  • CAREERS

Stories from those who dared, strategies for those who will! Are you a professional who is successful but stuck? Do you need to break through a career plateau that has you feeling uninspired, overlooked, and like your potential is being wasted? You know that you're meant for more, but you're unsure of the next step. Then you’ve found the right place, my friend, because this podcast is where Daring Breakthroughs come to life!  Welcome to Daring Breakthroughs, the podcast obsessed with helping professionals at all levels build unstoppable confidence, gain crystal clarity, and create powerful networking connections that create a competitive edge. We’re all about sharing practical strategies and inspiring stories from daring people who have achieved remarkable breakthroughs. If you can see it, you can BE it!  Your host, Jenn Landis, is a woman who gets it, because she’s BEEN it.  Jenn navigated her career from a part-time job at Walmart to ringing the bell on the NY Stock Exchange as a C-Suite leader with a multi-billion-dollar publicly traded company. Jenn pivoted out of her C-Suite executive role to chase her mission of helping professionals at all levels achieve their career ambitions. She is a professional speaker, author of the book “Break Up. Break In. Breakthrough!”, and founder of The Breakthrough Club for Women.  This podcast celebrates the inspiring stories of daring people who, like Jenn, have shattered barriers, made courageous career pivots, and overcome immense challenges to achieve their breakthroughs. Through fascinating interviews, Jenn delves into the real stories behind their success – their turning points, their struggles, and the strategies they used to get to the next level. Whether you're looking to climb the corporate ladder, launch a new venture, or completely reinvent your professional life, Daring Breakthroughs provides the inspiration, actionable advice, and supportive community you need to help you make your move. Each episode is packed with stories that let you see what’s possible, strategies to help you get there, and actionable guides to support you as you pursue your own breakthrough journey.  It's time to stop feeling stuck and start creating the career and life you desire. Join our network of ambitious professionals who are making it happen. Subscribe and listen to Daring Breakthroughs with Jenn Landis today. We dare you!

  1. Dr. Sasha Shillcutt: Boundaries, Burnout, and the Careers You're Allowed to Have

    5D AGO

    Dr. Sasha Shillcutt: Boundaries, Burnout, and the Careers You're Allowed to Have

    She Hit Success. Then Realized She Was Miserable. Here's What Changed Everything. What happens when you reach the top of your career and realize you don't like the life you built? In this episode of Daring Breakthroughs, host Jenn Landis sits down with cardiac anesthesiologist, entrepreneur, author, and leadership expert Dr. Sasha Shillcutt for a conversation that is equal parts honest and transformative. They cover burnout, boundaries, the feedback trap, career reinvention, and the one belief Jenn has built her entire methodology around: breakthroughs are a team sport. Dr. Sasha shares the hotel mirror moment that forced her to confront a life that looked successful from the outside and felt hollow from the inside. Jenn shares what it was like to sit inside a similar season as a senior executive and the hard lessons she wishes someone had handed her sooner. Together, they cover the messy, courageous, community-powered path that actually leads to a life that feels like yours. If you are a high-achieving professional wondering whether the next season gets to look different, this conversation is for you. =============================  Inside This Episode: 💡 The Hotel Mirror Moment -- The turning point that forced Sasha to confront burnout and choose a different path. 💡 Breakthroughs Are a Team Sport -- Why Sasha credits community and coaching, not solo grit, for her transformation. And why Jenn has said this for years. 💡 Why Boundaries Feel Impossible at the Top -- The counterintuitive truth: the higher you climb, the harder they become. 💡 You Won't Be Liked. But You Will Be Well. -- Sasha's straight-talk framework for understanding the real tradeoff of setting boundaries. 💡 Know Who Matters -- How to stop shapeshifting to please everyone and protect the only thing that can't be rebuilt: your authentic self. 💡 Women Are Over-Mentored and Under-Partnered -- Jenn's take on why mentorship alone will not move you forward, and what high-velocity partnerships actually look like. 💡 The Feedback Trap -- Why women receive disproportionately more feedback than men, and how to filter what actually deserves your energy. 💡 You Can Have Many Careers -- The permission slip Sasha finally gave herself, and why identity transitions are supposed to be part of the story. 💡 Ask for Help -- The advice Sasha gives every woman she coaches, and the one that tends to change everything. =============================  TIMESTAMPS 00:00 -- "You won't be liked... but you will be well."  00:28 -- Welcome to Daring Breakthroughs  04:40 -- The hotel mirror burnout moment  08:00 -- How change actually happens (community + coaching) 1 5:10 -- Why boundaries feel impossible at the top  17:30 -- You won't be liked, but you will be well (full context)  20:45 -- Know who matters: the most important career filter  27:45 -- The feedback trap and what to do about it  33:15 -- Building the Legacy Collective women's club  36:00 -- You can have many careers  40:10 -- Final advice: Ask for help =============================  Resources Mentioned in the Episode 📘 Between Grit and Grace and Brave Boundaries by Dr. Sasha Shillcutt https://www.becomebraveenough.com/books 🌐 Brave Enough (courses, conference, podcast, books) https://becomebraveenough.com 🎧 The Brave Enough Show Podcast https://podcasts.apple.com/us/podcast/the-brave-enough-show-for-women-physicians/id1438885403 =============================  Let's Connect 🎤 Hire Jenn to speak at your next event: https://www.jennlandis.com/speaking 📘 Get your copy of Break Up. Break In. Breakthrough!: https://www.jennlandis.com/book LinkedIn: https://www.linkedin.com/in/jennlandis Instagram: https://www.instagram.

    43 min
  2. The AI Leadership Trap with Tatiana Ferreira

    FEB 27

    The AI Leadership Trap with Tatiana Ferreira

    Is AI making you a lazy thinker? In this episode of Daring Breakthroughs, host Jenn Landis sits down with transformation executive and AI governance expert Tatiana Ferreira to discuss the evolving landscape of leadership in the age of AI. While many professionals are focused on adopting new tools, the real challenge lies in maintaining original thought and critical thinking. Tati shares her powerful 70-30 framework, explaining that while AI can handle the bulk of "busy work," there is a vital 30% that only humans can do: tasks requiring judgment, nuance, and compassion. We dive deep into why you should never outsource your thinking to a machine and how to use AI as a "challenge partner" to identify blind spots and shoot holes in your strategic plans. If you want to gain a competitive edge and lead with unstoppable confidence, you cannot afford to relegate your executive functioning to an algorithm. In This Episode, We Cover: 💡The Shift in Leadership: Why the "economy of output" is ending and the "economy of judgment" is beginning. 💡The 70-30 Framework: Understanding the specific 30% of work that requires a human touch. 💡The Danger of Outsourcing Thought: Why relying on AI for original ideas is a "warning" for modern executives.  💡AI as a Sparring Partner: How to use "alien intelligence" to challenge your hypotheses and find blind spots.  💡The Tati Test: A practical experiment to improve your AI prompts this week. ============================= TIMESTAMPS 00:00 — Introduction to Daring Breakthroughs  00:53 — Meet Tatiana Ferreira  02:13 — How AI is Changing Leadership  03:51 — The 70-30 Framework  04:40 — The Danger of Outsourced Thinking  07:55 — AI as "Alien Intelligence"  09:33 — Using AI for Career Reinvention  10:13 — The Role of Dissent  12:12 — This Week’s Tiny Tweak: The Tati Test  12:46 — Closing and Resources ============================ 📚 Resources Mentioned in the Episode Break Up. Break In. Breakthrough. — Jenn Landis ============================= Let’s Connect 🎤 Hire Jenn to speak at your next event: https://www.jennlandis.com/speaking 📘 Get your copy of Break Up. Break In. Breakthrough!: https://www.jennlandis.com/book 💬 Social Media: LinkedIn: https://www.linkedin.com/in/jennlandis Instagram: https://www.instagram.com/askjennlandis X: http://x.com/askjennlandis Facebook: https://www.facebook.com/profile.php?id= Connect with Tatiana Ferreira: Find Tati’s company and learn more about her work in transformation, AI governance, and executive leadership. 🌐 HarmonIQ Consulting: https://www.beharmoniq.com/ 🚀 Aurora AI Retail Accelerator: https://blueskyai.co/pages/aurora 💬 Connect with Tatiana Ferreira:  LinkedIn: https://www.linkedin.com/in/tatianaferreira/ Instagram: https://www.instagram.com/tatiana_g_ferreira/ ➡️ If this episode resonated with you, please LIKE the video, SUBSCRIBE for more Daring Breakthroughs, and COMMENT below with a moment when you said “yes” before you felt fully ready. #CareerReinvention #LeadershipMindset #AILeadership #ProfessionalGrowth #DaringBreakthroughs

    14 min
  3. Stop Waiting for Permission to Say "Yes": She Did It Before She Felt Ready

    FEB 20

    Stop Waiting for Permission to Say "Yes": She Did It Before She Felt Ready

    Stop waiting until you feel “ready.” That’s what we’re told, right? Get one more credential. One more approval. One more sign that it’s safe. In this episode, I sit down with Tatiana Ferreira to talk about what actually creates a breakthrough — and it’s not confidence first. It’s courage first. Tatianna (Tati) gets real about career reinvention and what it actually looks like emotionally, strategically, and professionally. She shares lessons from leading complex organizations, navigating multiple career pivots, and learning to say “yes” long before confidence arrives. This conversation dives deep into the emotional reality of reinvention, the risk of failure, and how leaders can actively create opportunities instead of waiting for them. If you’re navigating change, considering a career pivot, or learning how to grow through uncertainty, this episode is for you. Inside This Podcast Episode: 💡Saying Yes Before Confidence:  Why waiting for certainty keeps you stuck — and how bold yeses create momentum. 💡Courageous Yes vs Reckless Yes:  How to set limits and evaluate risk before taking big leaps. 💡Failure, Experimentation & Growth:  Why innovation requires failure budgets and personal investment. 💡The Emotional Reality of Reinvention: Why reinvention often means losing status, feeling invisible, and sitting with silence. 💡Building a Support Network:  Why you need a personal board that challenges you — not just supports you. 💡The Biggest Breakthrough Lesson:  Every major breakthrough begins with a yes. If this resonates, don’t just listen — take action. 🎙 Subscribe for more conversations on engineering professional breakthroughs. And if this episode made you think of someone who’s waiting for permission to go for it — send it to her. ============================= TIMESTAMPS 00:00 — The hardest part of reinvention: sitting with the silence 06:02 — Saying yes before confidence 12:03 — Courageous vs reckless yes 15:07 — Opportunities are created, not offered 18:19 — Losing status before momentum 22:44 — Every breakthrough starts with a yes 📚 Resources Mentioned in the Episode: Break Up. Break In. Breakthrough! Book by Jennifer (Jenn) Landis ============================= Let’s Connect 🎤 Hire Jenn to speak at your next event: https://www.jennlandis.com/speaking 📘 Get your copy of Break Up. Break In. Breakthrough!: https://www.jennlandis.com/book LinkedIn: https://www.linkedin.com/in/jennlandis Instagram: https://www.instagram.com/askjennlandis X.com: http://x.com/askjennlandis Facebook: https://www.facebook.com/askjenniferlandis/ Connect with Tatiana Ferreira:  Learn more about Tati's work in transformation, AI governance, and executive leadership: 🌐 HarmonIQ Consulting: https://www.beharmoniq.com/ 🚀 Aurora AI Retail Accelerator: https://blueskyai.co/pages/aurora 🔗 Connect with Tatiana Ferreira: LinkedIn: https://www.linkedin.com/in/tatianaferreirahttps://www.linkedin.com/in/tatianaferreira Instagram: https://www.instagram.com/tatiana_g_ferreira ➡️ If this episode resonated with you, please LIKE the video, SUBSCRIBE for more Daring Breakthroughs, and COMMENT below with a moment when you said “yes” before you felt fully ready. #CareerReinvention #LeadershipMindset #AILeadership #ProfessionalGrowth #DaringBreakt

    24 min
  4. Fired from your dream job? She was, too.

    FEB 13

    Fired from your dream job? She was, too.

    What do you do when you get fired from your dream job? In this podcast episode of Daring Breakthroughs, host Jenn Landis sits down with banking executive Becky Fields Wilson to discuss how to handle getting fired and find a better job. Becky shares her raw journey of being a bank president who was suddenly told she was "no longer needed" and had to clean out her desk the same day. This conversation is a masterclass in the professional mindset shifts for career growth. We dive deep into "Thought Work"—the practical science of taking negative thoughts captive and using your imagination to dream up your next big move rather than spiraling into worry. If you are currently navigating career setbacks in a tough economy, Becky’s "Positive on Purpose" framework provides the "bridge thoughts" you need to move from discouragement to your next great opportunity. Inside this Podcast Episode: The 90-Second Reset: How to disrupt the chemical flood of panic to make better strategic decisions.The Result Framework: Understand how Circumstances → Thoughts → Feelings → Actions create your results.Mastermind Groups: How to form a personal board of directors to normalize your experience and destroy imposter syndrome.Recession-Proofing: Why you don't have to "sign up" for an economic downturn and how to find thriving companies.============================= Resources Mentioned: The 90-Second Rule: Referenced by Jenn Landis, this concept was coined by neuroanatomist Dr. Jill Bolte Taylor in her work, My Stroke of Insight.Think and Grow Rich by Napoleon HillBreak Up. Break In. Breakthrough! by Jenn LandisCoaching insights from Bob Proctor and Brooke Castillo============================= Let’s Connect 🎤 Hire Jenn to speak at your next event: https://www.jennlandis.com/speaking 📘 Get your copy of Break Up. Break In. Breakthrough!: https://www.jennlandis.com/book LinkedIn: https://www.linkedin.com/in/jennlandis Instagram: https://www.instagram.com/askjennlandis X: http://x.com/askjennlandis Facebook: https://www.facebook.com/profile.php?id= Connect with Becky Fields Wilson: Find Becky on LinkedIn and YouTube to learn more about her speaking. Website: https://www.momentum90.com/ LinkedIn (Becky Fields Wilson): https://www.linkedin.com/in/becky-fields-wilson/ YouTube (Becky Fields Wilson): https://www.youtube.com/@beckyfieldswilson ➡️ If this episode resonated with you, please LIKE the video, SUBSCRIBE for more Daring Breakthroughs, and COMMENT below with a moment when you chose alignment over pressure. #CareerAdvancement #LeadershipMindset #JobLossRecovery #ProfessionalGrowth #PositiveOnPurpose

    43 min
  5. Your Boss Isn’t Your Sponsor — Here’s Why You’re Not Getting Promoted! (Ep. 11)

    11/07/2025

    Your Boss Isn’t Your Sponsor — Here’s Why You’re Not Getting Promoted! (Ep. 11)

    Are you feeling stuck at work, passed over for a promotion, or wondering why your boss will not promote you, even though you’re doing everything right? You’re not alone. Many professionals face promotion struggles and career stagnation because they have a manager, not a sponsor. In this episode of Daring Breakthroughs, leadership strategist Jenn Landis (author of "Break Up, Break In, Breakthrough!") reveals powerful career advancement tips and the truth behind common promotion myths that hold talented people back. A sponsor is your advocate behind closed doors—the person who can help you get promoted at work, open new opportunities, and accelerate your career growth. Jenn shares her proven 3-step “Sponsorship Chain Reaction” to help you get noticed by decision-makers and turn your friendly boss into a true career champion. 🔑 Here’s what you’ll learn:  💡 The difference between a coach, a mentor, and a sponsor 💡 Why demanding sponsorship never works (and what to do instead) 💡 Step 1: How to demonstrate your potential and be “sponsor-ready” 💡 Step 2: How to make your ambitions known without just asking for a promotion 💡 Step 3: The powerful strategy of making your boss look good (and why it’s not “kissing up”) 💡 A word-for-word script to start the sponsorship conversation with an executive Whether you’re facing workplace frustration, feeling undervalued at work, or wondering why you don’t get promoted, this video is packed with actionable career advice, leadership promotion advice, and career growth strategies to help you move up in your job. 🎯 Perfect for anyone who has: ✅ Got passed over for a promotion or passed over for promotion again ✅ A toxic workplace or bad boss who won’t recognize their potential ✅ Reached a career dead end or career stagnation ✅ Been told they’re “too good to promote” ✅ Struggled with visibility at work and want to learn how to increase visibility at work Watch this video to discover how to get promoted at work fast, unlock your career development, and achieve true professional growth and success. If you’ve ever said, “My boss won’t promote me” or wondered why am I not getting promoted at work, this episode will give you the mindset and strategy to finally get promoted, achieve your next career promotion, and fast-track your career advancement. 🔗 Connect with Jenn: ► Book: Break Up. Break In. Breakthrough! https://a.co/d/dxU9ehR ► Website and Free Resources to Support Your Next Breakthrough: https://www.jennlandis.com/yourbreakthroughguide ►Book Jenn to Speak at Your Next Event: https://www.jennlandis.com/speaking ► LinkedIn: https://www.linkedin.com/in/jennlandis/ ➡️ If this story inspired you, LIKE the video, SUBSCRIBE for more daring breakthroughs!

    12 min

  6. 10/30/2025

    Confident Communication: Speak So Executives Can't Ignore You (Ep. 10)

    Struggling to speak up in high-stakes meetings? Do you wish you could speak confidently to executives without feeling nervous or second-guessing yourself? You’re not alone. In this self improvement and personal development video, Jenn Landis, author of “Break Up. Break In. Breakthrough!” and a leadership strategist who climbed the corporate ladder from Walmart to Wall Street, shares how she transformed fear into confident communication. Through her personal story of facing an intimidating executive named “Frank,” Jenn reveals her 3-step Confidence Formula, a powerful guide to improve your communication skills, boost your public speaking skills, and speak like a leader in any room. 🔑 Here’s what you’ll learn: 💡 Overprepare Your Content – Master your material so your focus stays on communication, not memorization. 💡 Reframe the Threat – Recognize the real fear (like embarrassment or regret) and use visualization techniques to take control. 💡 Answer the Question, Not the Tone – Respond with confidence and clarity, demonstrating grace and composure under pressure. This episode is packed with communication tips, public speaking training, and actionable advice on how to improve communication skills, how to improve your voice, and how to speak with confidence, even in front of top executives. Whether you’re working on your leadership skills, honing your presentation skills, or simply learning how to improve your communication, this episode gives you practical public speaking tips to help you lead conversations, influence decisions, and earn respect. 🔗 Connect with Jenn: ► Book: Break Up. Break In. Breakthrough! https://a.co/d/dxU9ehR ► Website and Free Resources to Support Your Next Breakthrough: https://www.jennlandis.com/yourbreakthroughguide ►Book Jenn to Speak at Your Next Event: https://www.jennlandis.com/speaking ► LinkedIn: https://www.linkedin.com/in/jennlandis/ ➡️ If this story inspired you, LIKE the video, SUBSCRIBE for more daring breakthroughs!

    14 min
  7. Why You're Invisible at Work (And How to Fix It) (Ep. 9)

    10/24/2025

    Why You're Invisible at Work (And How to Fix It) (Ep. 9)

    Tired of doing incredible work, only to watch someone else get the credit? If you feel like the best-kept secret in your company, it's time to change that. In this video, executive coach and author Jenn Landis reveals why even the most talented professionals stay invisible and what you can do to fix it. Drawing from her bestselling book, "Break Up. Break In. Breakthrough!", Jenn shares her personal story of a failed pitch and unpacks a powerful 3-step formula for creating strategic visibility that gets you noticed by leadership. ✨ In this episode, you'll learn: 💡How to use the "Opportunity Compass" tool to identify high-value organizational pain points that leaders are eager to solve.  💡The win-win strategy of matching a company problem to a specific skill gap you need to close for your next promotion. 💡 How to frame your initiative as a strategic solution, making you an indispensable contributor instead of just another employee asking for more work. 💡 One simple action you can take TODAY to start your journey from invisible to influential. This isn't about working harder; it's about working smarter on the right things to accelerate your career trajectory. Stop waiting to be noticed and start creating your own breakthrough moments! 🔗 Connect with Jenn: ► Book: Break Up. Break In. Breakthrough! https://a.co/d/dxU9ehR ► Website and Free Resources to Support Your Next Breakthrough: https://www.jennlandis.com/yourbreakthroughguide ►Book Jenn to Speak at Your Next Event: https://www.jennlandis.com/speaking ► LinkedIn: https://www.linkedin.com/in/jennlandis/ ➡️ If this story inspired you, LIKE the video, SUBSCRIBE for more daring breakthroughs!

    9 min
  8. Building Workplace Villages: Heather Powers on Empowering Caregivers (Ep. 8)

    10/11/2025

    Building Workplace Villages: Heather Powers on Empowering Caregivers (Ep. 8)

    Are you a working caregiver feeling exhausted, overlooked, and unsupported? Have you ever been told you’re not pushing your team hard enough when, in truth, everyone is just trying to hold it all together? You’re not alone — and this episode is for you. In this episode of Daring Breakthroughs, Jenn Landis sits down with Heather Powers, former corporate executive and founder of The Power Lane, for an eye-opening conversation about caregiver burnout and the urgent need for more authentic leadership in today’s workplaces. Heather shares her powerful breakthrough moment — the day she was reprimanded for showing compassion to her team during the pandemic. That experience inspired her to leave a 30-year corporate career and build a new path focused on supporting working moms, caregivers, and leaders who are ready to create a true workplace village. 🔑 In this must-watch interview, you’ll discover: 💡The shocking truth that 75% of today’s employees are caregivers in some capacity — and what that means for companies. 💡How to build a Workplace Village, even if your leadership isn’t fully on board. 💡Actionable strategies for leaders to foster psychological safety and a culture of trust, empathy, and collaboration. 💡The powerful business case for retaining and engaging working mothers and caregivers, improving productivity and retention. 💡 Why creating a women community of support and understanding is essential for sustainable success. If you’re a leader who wants to build a thriving, resilient team, or a professional caregiver trying to balance family life and career ambitions, this episode will give you courage to pivot, find clarity, and lead with purpose.  🎨  Find our guest, Heather Powers and learn more about building a Workplace Village: Website: https://www.thepowerlane.com LinkedIn: Heather L. Powers 🔗 Connect with Jenn: ► Book: Break Up. Break In. Breakthrough! https://a.co/d/dxU9ehR ► Website and Free Resources to Support Your Next Breakthrough: https://www.jennlandis.com/yourbreakthroughguide ►Book Jenn to Speak at Your Next Event: https://www.jennlandis.com/speaking ► LinkedIn: https://www.linkedin.com/in/jennlandis/ ➡️ If this story inspired you, LIKE the video, SUBSCRIBE for more daring breakthroughs!

    37 min
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About

Stories from those who dared, strategies for those who will! Are you a professional who is successful but stuck? Do you need to break through a career plateau that has you feeling uninspired, overlooked, and like your potential is being wasted? You know that you're meant for more, but you're unsure of the next step. Then you’ve found the right place, my friend, because this podcast is where Daring Breakthroughs come to life!  Welcome to Daring Breakthroughs, the podcast obsessed with helping professionals at all levels build unstoppable confidence, gain crystal clarity, and create powerful networking connections that create a competitive edge. We’re all about sharing practical strategies and inspiring stories from daring people who have achieved remarkable breakthroughs. If you can see it, you can BE it!  Your host, Jenn Landis, is a woman who gets it, because she’s BEEN it.  Jenn navigated her career from a part-time job at Walmart to ringing the bell on the NY Stock Exchange as a C-Suite leader with a multi-billion-dollar publicly traded company. Jenn pivoted out of her C-Suite executive role to chase her mission of helping professionals at all levels achieve their career ambitions. She is a professional speaker, author of the book “Break Up. Break In. Breakthrough!”, and founder of The Breakthrough Club for Women.  This podcast celebrates the inspiring stories of daring people who, like Jenn, have shattered barriers, made courageous career pivots, and overcome immense challenges to achieve their breakthroughs. Through fascinating interviews, Jenn delves into the real stories behind their success – their turning points, their struggles, and the strategies they used to get to the next level. Whether you're looking to climb the corporate ladder, launch a new venture, or completely reinvent your professional life, Daring Breakthroughs provides the inspiration, actionable advice, and supportive community you need to help you make your move. Each episode is packed with stories that let you see what’s possible, strategies to help you get there, and actionable guides to support you as you pursue your own breakthrough journey.  It's time to stop feeling stuck and start creating the career and life you desire. Join our network of ambitious professionals who are making it happen. Subscribe and listen to Daring Breakthroughs with Jenn Landis today. We dare you!

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