Bold Moves: How Did You Know | Midlife Career Change & Life Transitions for Women

Bold Moves: How Did You Know | Midlife Career Change & Life Transitions for Women

por Kristen Rocco: Midlife Career Coach & Mentor
CarrerasSuperación personal
Temporada 5
The "Menopause Penalty": Is Midlife Biology Stalling Your Bold Move? with Menopause Practitioner & Board-Certified OB-GYN Dr. Sarah Berg
Just as women in midlife hit their stride and prepare to step into their emboldened midlife click, they often collide with an invisible biological speed bump: the menopause transition. Without clear education, this biological event leads women to quietly retreat, second-guess their capability, and pause the very bold moves that would fulfill them. In this episode, host Kristen Rocco sits down with board-certified OB-GYN, certified menopause practitioner, and founder of Selfority, Dr. Sarah Berg. Together, we dismantle the shame, isolation, and silence surrounding the menopause transition in the workplace so you can take back control, release the self-blame, and get the clarity and tools you need to regain your health to make your bold moves. Inside the episode, learn: Dr. Sarah Berg’s Bold Move: How leaving the security of a 15-year clinical practice to found Selfority started as a realization in her medical office and crystallized during a trail-running retreat in the Oregon woods. The clear medical distinction between perimenopause and menopause, and why viewing it as one continuous transition helps you advocate for your health. Common and uncommon menopause and perimenopause symptoms and why sudden mood disruptions, including perimenopausal rage, are biological events—not personal or professional failures. The staggering data behind the "menopause penalty." How bringing education directly into organizations protects female leadership pipelines and why companies that support women in midlife perform 30% better financially. Practical advice for bringing perimenopause and menopause-related questions to doctor visits, knowing when it’s time to "break up" with your provider, and managing care across multiple specialists. The two non-negotiable daily habits you can start right now to protect your energy, reclaim your vitality, and power your next bold moves. Bold Moves: How Did You Know? is for women at a midlife crossroads ready to navigate a career pivot, launch a business, start a project, or make a life transition with confidence. Each episode delivers the essential mindset shifts and actionable advice you need to conquer fear, silence imposter syndrome, stop people-pleasing, and shed the outdated identities that no longer serve you—so you can finally start designing a life on your own terms. Join the Bold Moves Newsletter: kristenrocco.substack.com Connect with Guest Dr. Sarah Berg Web: www.selfority.com. Substack: https://sarahbergmd.substack.com/ IG: https://www.instagram.com/selfority/ YouTube: https://www.youtube.com/@Selfority Connect w/ Host Kristen Rocco Substack: kristenrocco.substack.com YouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcast IG: @kristenrocco LinkedIn: /kristenrocco Love the Show? If this episode helped you step closer to your own midlife click, please leave us a five-star rating and review on Apple Podcasts or Spotify!
T5 · E74
28 jul 2026
58:52
Motherhood, Ambition, Midlife, and Reinventing Yourself with That’s Total Mom Sense Host Kanika Chadda-Gupta
In this episode, we're shattering the old societal scripts and stepping into a powerful conversation that sits at the exact intersection of motherhood, ambition, and midlife. Bold Moves Host Kristen Rocco is joined by Kanika Chadda Gupta, host of the top-ranked podcast That’s Total Mom Sense. Together, they completely flip the narrative on what happens to our professional drive after having kids. Instead of shrinking or playing small, they explore how raising a family can actually be the ultimate catalyst for reinventing yourself and making the boldest career moves of your life. We Discuss: The Motherhood Advantage: Why a mother's ambition doesn't halt after having kids; it grows. We discuss how parenting deepens essential leadership traits like empathy, acute problem-solving, and patience. Ruthless Prioritization: Navigating the intense identity shifts of midlife and parenting, learning how to tune out the noise and protect your energy. Expert "Mom Sense": Kanika shares the absolute best parenting wisdom she’s parsed from her own iconic show guests, including Chelsea Clinton, Kelly Rowland, and Dr. Becky. Motherhood Legacy: Why letting your kids see you reinvent yourself and make bold moves is the ultimate parenting gift. Bold Moves: How Did You Know? is for women at a midlife crossroads ready to navigate a career pivot, launch a business, start a project, or make a life transition with confidence. Each episode delivers the essential mindset shifts and actionable advice you need to conquer fear, silence imposter syndrome, stop people-pleasing, and shed the outdated identities that no longer serve you—so you can finally start designing a life on your own terms. Join the Bold Moves Newsletter: kristenrocco.substack.com Your next chapter is yours to write! If today’s story made your inner whisper feel more like a scream, don’t let the autopilot of life drown it out again. Join a community of women all making bold moves right alongside you. Connect w/ Kanika Chadda-Gupta: Instagram: @ kanikachaddagupta thatstotalmomsense.com Connect w/ Host Kristen Rocco Substack: kristenrocco.substack.com YouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcast Love the Show? If this episode helped you step closer to your own midlife click, please leave us a five-star rating and review on Apple Podcasts or Spotify! Kanika shared the perfect prompt to inspire your review: "Share your favorite piece of advice from the episode."
T5 · E73
14 jul 2026
32:02
Why "Self-Made" is a Lie: Every Bold Mover Needs a Mentor. How to Find One and Make it Count
There is no such thing as self-made. Success only happens when you have a dedicated network scaffolding and supporting you along the way, according to today's guest, Kanika Chadda-Gupta. From covering breaking news at CNN International to launching her own top-ranked media platform, That's Total Mom Sense, Kanika Chadda-Gupta opens up about how having a mentor has transformed her career. She shares how early guidance from NBC’s Willard Shepard pushed her to make her mark globally, and how cultivating a deep, human-to-human relationship with former Hello Sunshine CEO Sarah Harden blossomed into game-changing strategic mentorship. Kanika shares how mentorship has propelled her bold moves, what she’s learned from cultivating these relationships, and she gives actionable tips and advice on the most-asked questions about mentorship and mentor-mentee partnerships: How do you approach someone you admire to become your mentor? What’s the best way to structure the mentor-mentee relationship to ensure it’s purposeful, actionable, and strategic? What advice would you give to women on how to approach mentorship in a way that feels authentic, confident, and relationship-driven rather than transactional? How can a mentor help propel your bold move? If you're making a bold career pivot, navigating a major career decision, or making a bold move, this episode will give you the blueprint for working with a mentor who can propel you forward. Bold Moves: How Did You Know? is for women at a midlife crossroads ready to navigate a career pivot, launch a business, start a project, or make a life transition with confidence. Each episode delivers the essential mindset shifts and actionable advice you need to conquer fear, silence imposter syndrome, stop people-pleasing, and shed the outdated identities that no longer serve you—so you can finally start designing a life on your own terms. Join the Bold Moves Newsletter: kristenrocco.substack.com Your next chapter is yours to write! If today’s story made your inner whisper feel more like a scream, don’t let the autopilot of life drown it out again. Join a community of women all making bold moves right alongside you. Connect w/ Kanika Chadda-Gupta: Instagram: @ kanikachaddagupta thatstotalmomsense.com Connect w/ Host Kristen Rocco Substack: kristenrocco.substack.com YouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcast Love the Show? If this episode helped you step closer to your own midlife click, please leave us a five-star rating and review on Apple Podcasts or Spotify! Kanika shared the perfect prompt to inspire your review: "Share your favorite piece of advice from the episode."
T5 · E72
30 jun 2026
44:01
NEW Podcast Club: Living Your Authentic Life by Finding Your Authentic Truth
Welcome to a brand-new segment on the podcast: the Bold Moves Podcast Club! Think of it just like a book club, but instead of pages, we are unpacking the powerful insights shared by the guests on the Bold Moves: How Did You Know? podcast. In this episode, host Kristen Rocco takes a deep dive into her recent conversation with Jen DeGroff to analyze the big, messy question so many high-achievers face: How do I figure out what I really want after years of performing in a role that no longer serves me? Essentially, how do I live an authentic life? If you feel like your authentic life is buried under a mountain of external expectations, "shoulds," and endless to-do lists, this episode is the start to answering the questions that will move you forward. It's your first step to stop performing and start living an authentic life. This episode dissects the wisdom and insights shared from Jen's story about finding her authentic truth, which is directly before this one in the podcast feed, called "The Toxic Cost of Burnout and Stress: How to Stop Performing Life and Start Living It." In this Bold Moves Podcast Club episode, we cover: The Trap of "Introjected Regulation" Your Body’s Alarm System The Power of Autotelic Activities for Tuning Your Authentic Truth. Neuroplasticity in Action Bold Moves: How Did You Know? is for women at a midlife crossroads ready to navigate a career pivot, launch a business, start a project, or make a life transition with confidence. Each episode delivers the essential mindset shifts and actionable advice you need to conquer fear, silence imposter syndrome, stop people-pleasing, and shed the outdated identities that no longer serve you—so you can finally start designing a life on your own terms. Join the Bold Moves Newsletter Your next chapter is yours to write! If today’s story made your inner whisper feel more like a scream, don’t let the autopilot of life drown it out again. Join a community of women all making bold moves right alongside you. 🔗 Subscribe here: kristenrocco.substack.com What you get every send: 🧠 The exact mindset shifts required to break free from what’s keeping you stuck. 💡 Behind-the-scenes insights from world-class Bold Movers. 🌱 Bite-sized micro-actions you can start using immediately to write your next chapter. Connect with Host Kristen Rocco Substack: kristenrocco.substack.com Instagram: @kristenrocco YouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcast 🌟 Enjoyed this new Podcast Club format? Hit follow, leave a rating and review, and let Kristen know your thoughts!
T5 · E71
23 jun 2026
19:52
The Toxic Cost of Burnout and Stress: How to Stop Performing Life and Start Living It (feat. Jen DeGroff of TrueIcon)
Are you feeling trapped in a career that no longer serves you, perhaps even battling burnout from striving and overachieving for decades on end? Host Kristen Rocco sits down with Jen DeGroff, a remarkable woman who transformed her life from high-pressure corporate leadership to a value-aligned career as the founder of TrueIcon and a passionate personal trainer. Jen's story is a testament to how a midlife career change can heal burnout when you embrace your true, authentic self. As Jen reflects on her bold moves journey and how she reinvented her life and career, she opens up about the relentless pursuit of perfection and achieving that once defined her life, the toll it took on her health, and the pivotal health events that sparked her desire for change. 🎧 Tune in and hear how Jen overcame building an exhausting, inauthentic life and the burnout it caused: The toxic cost of performing life versus living it, and exactly how much energetic bandwidth you waste trying to maintain a "perfect-on-paper" illusion. Why the first "no" should never come from you—and how to stop letting unconscious fear talk you out of your biggest ideas before you even try. How to actively leverage neuroplasticity to shatter a fixed mindset, rewrite your daily habits, and realize your identity is never permanently stuck. A practical way for tuning into your gut by training yourself to recognize exactly what a physical "yes," "no," and "neutral" state feels like in your body. Jen’s breakthrough that perfectly illustrates how to guide yourself away from the habit of saying "I can't" and straight into your personal power. Bold Moves: How Did You Know? is for women at a midlife crossroads ready to navigate a career pivot, launch a business, start a project, or make a life transition with confidence. Each episode delivers the essential mindset shifts and actionable advice you need to conquer fear, silence imposter syndrome, stop people-pleasing, and shed the outdated identities that no longer serve you—so you can finally start designing a life on your own terms. Join the Bold Moves Newsletter here: kristenrocco.substack.com Connect w/ Guest Jen DeGroff: Website: beatrueicon.com Connect w/ Host Kristen Rocco Substack: kristenrocco.substack.com Instagram: @kristenrocco YouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcast 🌟 Love the Show? If this episode helped you step closer to your own midlife click, please leave us a five-star review on Apple or Spotify! Jen shared the perfect prompt to inspire your review. Answer: What inspired you about today's episode?
T5 · E70
16 jun 2026
42:53
Reinvent Yourself in Midlife: The No-BS Mindset Shifts You Need (feat. Colleen Kochannek of The 3rd Act Lab)
How do you figure out what you really want when you've spent decades following predefined expectations of you–from society, family, culture? If you're a woman standing at a midlife crossroads, feeling stuck, or trying to figure out how to make a career pivot or life transition, this is your blueprint for the mindset shifts and tips you need to reinvent yourself in midlife. It starts with throwing out all the scripts that tell us who we are and what we’re supposed to do. Host Kristen Rocco sits down with Colleen Kochannek, a woman who famously declared to the world that at 58, she was finally living her first life. After many midlife wake-up calls that included an unexpected career layoff and profound personal losses, Colleen relied on her resilience, stopped performing the scripts of her past and stepped boldly into her self-proclaimed selfish era, using actionable mindset strategies to build a life entirely “by her, for her, and about her.” Together, Kristen and Colleen decode the mindset shifts and midlife click—the exact moment she stopped repeating the patterns that kept her small and started taking the bold micro-actions that create the life she actually wants. 🎧 You’re going to love Colleen’s no-bs reality check on: Why putting your own needs first in every single decision is the ultimate act of personal reclamation. How to actively train your brain to question everything—from your lifelong career path down to what you want for breakfast. Using micro-experiments to outsmart the danger signals your brain sends whenever you try something new. Why you don’t need to wait to feel confident before you make a move. Bold Moves: How Did You Know? is for women at a midlife crossroads ready to navigate a career pivot, launch a business, start a project, or make a life transition with confidence. Each episode delivers the essential mindset shifts and actionable advice you need to conquer fear, silence imposter syndrome, stop people-pleasing, and shed the outdated identities that no longer serve you—so you can finally start designing a life on your own terms. Join the Bold Moves Newsletter here: kristenrocco.substack.com Your next chapter is yours to write! If today’s story made your inner whisper feel more like a scream, don’t let the autopilot of life drown it out again. Join a community of women all making bold moves right alongside you. Connect w/ Guest Colleen Kochannek: Instagram & TikTok: @ColleenKochannek Website: stan.store/colleenkochannek Connect w/ Host Kristen Rocco Substack: kristenrocco.substack.com Instagram: @kristenrocco YouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcast 🌟 Love the Show? If this episode helped you step closer to your own midlife click, please leave us a five-star review on Apple Podcasts or Spotify! Colleen shared the perfect prompt to inspire your review: "I don't need to find confidence to go be bold. I can just go be bold."
T5 · E69
2 jun 2026
36:49
Temporada 4
Bold Moves: Momentum-Building Strategies for the Year of the Horse
In this Season 4 finale, I (host Kristen Rocco here!) explore four essential strategies that will help you create momentum for your bold move in 2026—the Year of the Horse. In the Chinese zodiac, the Horse represents unbridled speed and power, making this the perfect year to stop over-calculating and finally accelerate your bold move. However, even a horse at full speed can stumble if it loses its footing; this episode is your guide to surviving the "messy middle" of a bold move where the initial rush fades and the daily work begins. Bringing together the best insights from Season 4’s entrepreneurs, corporate leaders, and a former CIA strategist, this finale provides a tactical roadmap for generating momentum when the road gets rough. Whether you're building early momentum for a new bold move or need to break through a moment of paralysis, you’ll learn how to take the reins and turn potential stumbles into breakthroughs. Get the Bold Moves Momentum Audit Make your plan for maintaining momentum through the messy middle of a bold move. Find it on my Substack here: https://open.substack.com/pub/kristenrocco/p/momentum-building-strategies-for? What You'll Learn In This Episode Strategy 1: Building Early Momentum Learn what Bold Movers do before they make the bold move to fuel momentum from the get-go. Strategy 2: Maintaining Momentum Discover the internal tracks–the pre-built rails of systems, mindsets, and habits that allow your work to continue moving forward, even when your initial energy begins to fade. Strategy 3: Borrowing Momentum Learn how others can help you generate forward progress in your bold move, as well as the difference between "Supporters" and "Elevators"—and why you need the latter to reach the next level. Strategy 4: Restarting Momentum Explore what to do when you hit the "Valley of Trials" and your initial motivation completely disappears—including a 90-second biological hack for breaking through paralysis. 0:00 Year of the Horse Energy 4:08 Building Early Momentum 10:38 Maintaining Momentum 20:37 Borrowing Momentum 28:20 Restarting Momentum 35:45 Bold Moves Momentum Wisdom Featured Guests This Season Each guest’s full episode is waiting for you in this podcast's back catalog. Erin Fortin - Process Engineer turned Bicoastal Photography Studio Owner Sherehan Ross - Digital Marketing & AI Expert Rachel Lipson - Founder, Blue Balloon Songwriting School Genevieve Dozier - Corporate Leader & Entrepreneur Michelle Beyo - Future of Finance Disruptor and Entrepreneur Tyler Hakes - Entrepreneur & Growth Strategist Ashley Cheretes - Corporate AI Marketing Leader Simone Knego - Confidence Coach Mike Krupit - Executive Coach Kelly McGannon - Former CIA Strategist Love the Show? If these stories of bold moves have inspired you, please leave a rate and review on Apple Podcasts or Spotify. Your support helps other Bold Movers find this show and join our community! Connect with Kristen Stay connected between seasons on the Bold Moves Substack for behind-the-mic lessons and insights from my Bold Moves journey. Join me: kristenrocco.substack.com
T4 · E68
19 feb 2026
42:18
Building a Portfolio Career in Midlife with Genevieve Dozier
You might be asking yourself the question that haunts so many of us: “Is this it?” You’ve checked all the boxes. You have the title, the stability, and the resume. But internally, there is a restless voice asking if there's something more you’re meant for. The problem is, the idea of a major career transition, burning it all down and starting over, feels terrifying. Genevieve Dozier is here to prove that you can build a portfolio career that scratches all the itches. Genevieve is a Fintech leader who refused to accept the binary choice of "Corporate Executive" OR "Creative Entrepreneur." Instead, she built a Portfolio Career, simultaneously climbing the ladder at major financial institutions like BB&T and Fiserv while building her own business, Warpaint Consulting. In this episode, Genevieve challenges the "What if?" anxiety with a powerful new question: "Why not?" Why not build an "insurance policy" for your career? Learn how a side hustle can be more than a passion project; it can be a safety net against layoffs and corporate volatility. Why not be a C-Suite leader and a creative entrepreneur? Discover how to write books, speak on stages, and consult without losing your status as a respected executive. Why not start right now, exactly where you are? See why you don’t need to wait for the "perfect time." Genevieve wrote her book on airplane tray tables while traveling for work, proving that boldness happens in the margins of your busy life. This episode has it all: Genevieve challenges conventional career wisdom, normalizes that it's okay to step in and out of a career, and shares exactly why it's important to build a portfolio career that serves your professional growth. She was able to become a portfolio career trailblazer because she sought out mentors and advice that opened her mind to what was possible. Now, she’s paying it forward to be that example for you. Join the Bold Moves Newsletter here: kristenrocco.substack.com Your next chapter is yours to write! If today’s story made your inner whisper feel more like a scream, don’t let the autopilot of life drown it out again. Commit to becoming the main character in your life by taking the micro-action of subscribing to the Bold Moves newsletter, and together, let’s make your bold move happen. What you get every send: 🧠 The exact mindset shifts required to break free from what’s keeping you stuck. 💡 Behind-the-scenes insights from world-class Bold Movers. 🌱 Bite-sized micro-actions you can start using immediately to write your next chapter. Join a community of women all making bold moves right alongside you. Connect with Guest Genevieve Dozier: On LinkedIn: www.linkedin.com/in/genevievedozier Website: https://warpaintconsulting.com/ Connect with host Kristen Rocco Substack: kristenrocco.substack.com LinkedIn: /kristenrocco Instagram: @kristenrocco
T4 · E67
5 feb 2026
55:39
He Hid a Secret for 35 Years. How Vulnerability Changed His Life (feat. Mike Krupit, CEO, Trajectify)
What if you saw your vulnerability as a superpower rather than a sign of weakness? Mike Krupit spent decades as a Silicon Valley daredevil, launching eight startups and handling millions without flinching, but he admits his most important Bold Move wasn't in business; it was finally taking off the mask he’d worn for 35 years. In this episode, Mike peels back the layers on how he used professional risks to shield himself from personal vulnerability, and why dismantling the "tower" he built around his emotions was the only way to live an authentic life. If you are projecting perfection, but underneath, you're really living behind a mask, you are likely causing your own setbacks and dissatisfaction. We also dive into a tool called Autocratic Coaching to explain how micro-instructions can short-circuit the panic that comes with being vulnerable. Plus, we tackle the Sunk Cost Fallacy and why pivoting from something you've invested years in can actually be a great victory. Tune in now to hear why vulnerability is the key that unlocks a whole lot more of your potential and how to start, one step at a time. 0:00 - Meet Mike Krupit, CEO of Trajectify 1:52 - Personal Risk-Taking Leads to His Boldest Move 7:44 - Mike's Professional Career 15:27 - The Catalytic Moment that Changed Everything 16:47 - Vulnerability Requires Courage 25:11 - Sunk Cost Fallacy 33:24 - If Not Now, When? Join the Bold Moves Community And over on Substack, we’re dropping the masks and building our "Bold Moves" muscle —one messy step at a time. Join us as we figure it out together: kristenrocco.substack.com. Connect with Guest Mike Krupit: Website: www.trajectify.com Connect with host Kristen Rocco Substack: kristenrocco.substack.com LinkedIn: /kristenrocco Instagram: @kristenrocco
T4 · E66
22 ene 2026
37:47
When Not to Trust Your Gut + Leaving Your Comfort Zone (feat. Rachel Lipson, 2x Founder)
Today, we're flipping the script on a piece of advice we usually accept as a universal truth: trust your gut. This is a vital conversation because it challenges a well-known convention about your inner voice, particularly if you struggle with anxiety. You’re told constantly to trust your gut. It is the golden rule of intuition—if something feels wrong, don't do it. But what happens when your gut is driven by anxiety instead of wisdom? For Rachel Lipson, founder of Blue Balloon Songwriting School and Brooklyn Family Travelers, learning not to trust your gut was the key to her bold move. As a child battling agoraphobia, Rachel’s intuition screamed at her to stay safe and stay home. If she had listened to that feeling, she never would have left Michigan or her reputable teaching job for something more that was calling to her. In this episode, Rachel shares how she rejected the instinct to seek safety and moved to New York City to force herself out of her comfort zone. She reveals why “trust your gut” might be problematic advice for anyone with anxiety, and how she learned to proceed with caution instead of paralysis. Rachel also walks us through her 17-year journey of entrepreneurship, sharing her brilliant metaphor for sustaining a business. Plus, we cover her latest pivot into Brooklyn Family Travelers, where she teaches families how to use credit card points to explore the world. Hit play now and learn why you might need to stop trying to trust your gut to finally make your bold move! Join the Bold Moves Newsletter here: kristenrocco.substack.com Your next chapter is yours to write! If today’s story made your inner whisper feel more like a scream, don’t let the autopilot of life drown it out again. Commit to becoming the main character in your life by taking the micro-action of subscribing to the Bold Moves newsletter, and together, let’s make your bold move happen. What you get every send: 🧠 The exact mindset shifts required to break free from what’s keeping you stuck. 💡 Behind-the-scenes insights from world-class Bold Movers. 🌱 Bite-sized micro-actions you can start using immediately to write your next chapter. You don't have to do this alone. Join a community of women all making bold moves right alongside you. kristenrocco.substack.com 🌟 Love the Show? If this episode helped you step closer to your own midlife click, please leave us a five-star review on Apple Podcasts or Spotify! Connect with Guest Rachel Lipson: Brooklyn Family Travelers: brooklynfamilytravelers.substack.com Blue Balloon Songwriting School: blueballoonschool.com Connect with host Kristen Rocco Substack: kristenrocco.substack.com LinkedIn: /kristenrocco Instagram: @kristenrocco
T4 · E65
6 ene 2026
53:52
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