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

Hosted by Kristen Rocco: Midlife Career Coach & Mentor

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Jun 2026

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Bold Moves: How Did You Know? is the podcast for women at a midlife crossroads ready to navigate a career pivot, launch a business, or make a life transition with confidence. Host Kristen Rocco, a Bold Moves Coach, helps you move beyond the "midlife crisis" and directly into your "midlife click" by unlocking the essential mindset shifts and 'how to' strategies required for reinvention. Whether you’ve hit a wake-up call like a layoff or health crisis, or you’re feeling the burnout of high-performing in a career that no longer lights you up, Kristen helps you answer the question: "Is this all there is?" This show deconstructs the stories of "Bold Movers"—women who have been exactly where you are and found the courage to pursue their dreams. Each episode provides the mindset shifts and actionable advice you need to stop people-pleasing, shed identities that no longer fit, and start designing a life on your own terms. We dive into personal growth, self-improvement, and career transitions, mapping out the internal mindset shifts behind the exact questions you’re likely asking yourself right now: How do I figure out what I really want after years of following a prescribed, traditional path? How do I find the courage to step out of my comfort zone and make a career pivot? How do I overcome imposter syndrome and limiting beliefs? How do I balance my desire for purpose with my need for security? What are the micro-actions I can take today to build momentum? How do I decouple my worth from my job title? How do I stop living by the "shoulds" and find true alignment? How do I get the confidence to pursue something I’ve never done before? It’s been years since I’ve listened to my inner voice—how do I start now? Here, we turn down the external volume of societal expectations to help you find the inner clarity to make the move you’ve been dreaming of. It’s time to stop repeating the patterns that keep you stuck or playing small. It’s time to start taking the bold micro-actions that create the life you actually want. Your next bold move starts right here!

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June 16, 202642 min

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.Episode Resource:Listen to "Ex-CIA Analyst’s Top Secrets: Mind-Body Intelligence & Bold Move Intel, Revealed" and learn how to listen to your gutJoin the Bold Moves Newsletter here: kristenrocco.substack.comYour 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!Subscribe here: Kristenrocco.substack.comConnect w/ Guest Jen DeGroff:Website: beatrueicon.comConnect w/ Host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenroccoYouTube: 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?

June 2, 202636 min

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.Join the Bold Moves Newsletter here: kristenrocco.substack.comYour 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.Connect w/ Guest Colleen Kochannek:Instagram & TikTok: @ColleenKochannekWebsite: stan.store/colleenkochannekConnect w/ Host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenroccoYouTube: 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."

February 19, 202642 min

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 AuditMake 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 EpisodeStrategy 1: Building Early MomentumLearn what Bold Movers do before they make the bold move to fuel momentum from the get-go.Strategy 2: Maintaining MomentumDiscover 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 MomentumLearn 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 MomentumExplore 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 Energy4:08 Building Early Momentum10:38 Maintaining Momentum20:37 Borrowing Momentum28:20 Restarting Momentum35:45 Bold Moves Momentum WisdomFeatured Guests This SeasonEach guest’s full episode is waiting for you in this podcast's back catalog.Erin Fortin - Process Engineer turned Bicoastal Photography Studio OwnerSherehan Ross - Digital Marketing & AI ExpertRachel Lipson - Founder, Blue Balloon Songwriting SchoolGenevieve Dozier - Corporate Leader & EntrepreneurMichelle Beyo - Future of Finance Disruptor and EntrepreneurTyler Hakes - Entrepreneur & Growth StrategistAshley Cheretes - Corporate AI Marketing LeaderSimone Knego - Confidence CoachMike Krupit - Executive CoachKelly McGannon - Former CIA StrategistLove 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 KristenStay 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

February 5, 202655 min

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.comYour 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/genevievedozierWebsite: https://warpaintconsulting.com/Connect with host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenrocco

January 22, 202637 min

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 Trajectify1:52 - Personal Risk-Taking Leads to His Boldest Move7:44 - Mike's Professional Career15:27 - The Catalytic Moment that Changed Everything16:47 - Vulnerability Requires Courage25:11 - Sunk Cost Fallacy33:24 - If Not Now, When?Join the Bold Moves CommunityAnd 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.comConnect with host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenrocco

January 6, 202653 min

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.comYour 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.comBlue Balloon Songwriting School: blueballoonschool.comConnect with host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenrocco

December 16, 202542 min

Surviving a Stroke, Leaving Intel, and Building a Business with Erin Fortin

Do you need a wake-up call to start following your dreams? And a roadmap for building a business that supports them?Then let me tell you about my guest today, Erin Fortin.In July 2024, Erin was in the prime of her life. She was healthy, active, and focused on building a thriving business. But during a routine jog with her husband, her world went black.At just 37 years old, Erin suffered a stroke—a moment that stopped her in her tracks and completely reshaped her perspective on what it actually means to make a bold move.Today’s episode is about that wake-up call. It’s about the shift from feeling invincible to realizing that we don't get a vote on when our time is up. This conversation of building her business is viewed through the lens of the urgent, new philosophy she now lives by: Don't Wait.Before her health scare, Erin made a massive pivot from a "corporate robot job" as a chemist at Intel Corporation to building a business from the ground up: Erin Fortin Photography.We discuss exactly how she navigated that transition and the systems required for building a business that could survive—and even thrive—during her six-month medical recovery.We dive deep into:The Wake-Up Call: Erin’s candid story of surviving a stroke and discovering a hole in her heart she never knew existed.The "Corporate Robot" Job: How Erin knew it was time to trade her lab coat for a camera lens.The Math of the Leap: How she reverse-engineered her expenses and runway before quitting corporate life.Systems & Scaling: The specific tools and delegation strategies that kept her bicoastal business running while she was in the hospital.📸 The Full-Circle Moment: A behind-the-scenes look at photographing an event in Gloria Steinem's living room.Erin’s Bold Moves Advice: "We don't get a vote as to when and where and how we go. So do it now. Do it scared. Don't wait."Love this episode? There's a whole community of Bold Movers over on Substack. Join us and build your bold moves muscle with us! https://kristenrocco.substack.comConnect with Guest Erin Fortin:Website: erinfortinphotography.comInstagram: @erinfortinphotoConnect with host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenroccoMentioned in this Episode:Bold Moves: How Did You Know episode: The Real Cost of Low (And how to Fix It) with Confidence Coach Simone Knego

December 2, 202551 min

How Women Can Build Unshakeable Confidence & Beat Imposter Syndrome with Confidence Coach Simone Knego

Did you know that women typically apply for jobs only when they meet 100% of the qualifications, while men apply when they hit just 60%? Even more concerning, nearly 80% of women struggle with low self-esteem and shy away from self-advocacy at work.This isn’t a competence gap. It’s a confidence gap.I sat down with Confidence Coach Simone Knego to discuss how women can start chipping away at these statistics by building unshakeable self-confidence.Simone is a best-selling author, two-time TEDx speaker, and the co-host of the podcast Her Unshakeable Confidence. But her journey wasn't a straight line. For years, she battled her inner critic of self-doubt rooted in past trauma and the pressures of comparison.From raising six children to summiting Mount Kilimanjaro, Simone discovered that confidence isn't something you are born with; it’s something you build in the messy, chaotic moments of everyday life. In this episode, she shares the raw truth about the cost of under-confidence and the practical tools she used to go from unsure to unshakeable.Simone teaches us:The REAL Method: A four-step framework (Respect yourself, Embrace your failures, Ask for what you want, Live without limits) to build lasting self-esteem.The "Control-Alt-Delete" Hack: A mental strategy to identify false narratives.How to rewire your brain: Why positive affirmations work scientifically and the specific "5 I's" Simone uses every morning.Reframing Imposter Syndrome: How to stop justifying your existence by dropping the word "just" (e.g., "I'm just a mom") and why feeling underqualified is often a sign of growth.Join the Bold Moves Newsletter here: kristenrocco.substack.comYour 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. 🌟 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 host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenroccoConnect with Guest Simone KnegoWebsite: simoneknego.comBook: Real Confidence: A Simple Guide to Go from Unsure to Unshakeable at realconfidencebook.comSimone's reflection on how climbing Mount Kilimanjaro changed her life: https://simoneknego.com/how-climbing-a-mountain-can-change-your-life/

November 18, 202552 min

How We Built It: Content Marketing in the Age of AI

I'm so excited to be joined by a special co-host for this episode, Tyler Hakes. Tyler is the principal at the content marketing agency, Optimist, and we’ve been collaborating on a new project!In this “How We Built It” episode, Tyler and I pull back the curtain on our recent collaboration, where we launched a new methodology for content marketing called the Authority Moat Model. We show you how you can turn industry chaos—like the disruption we've all seen from AI—into a new market opportunity.Listen in to get the practical, three-part framework I developed from our process. We'll walk you through how to spot a trend, diagnose the real problem or unmet need it creates, and architect an innovative solution. This is a real-world case study for making a bold move inside of your bold move, whether you're an entrepreneur or an intrapreneur.And if marketing is your business, you’re in luck. We explain how our Authority Moat Model builds compounding authority and tangible ROI for your brand, inspiring trust with your audience in a way that AI never can.Love this episode? There's a whole community of Bold Movers over on Substack. Join us and build your bold moves muscle with us! https://kristenrocco.substack.comConnect with host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenroccoConnect with Co-host Tyler HakesOn LinkedIn: https://www.linkedin.com/in/tyler-hakes/Read our Authority Moat Model Transformation Narrative: https://www.yesoptimist.com/authority-moat-model/

November 4, 202545 min

Failing Forward with Michelle Beyo, CEO of Finavator

Most people learn the rules and play the game. But what happens when you reject the rules everyone else accepts? For Michelle Beyo, CEO and founder of Finavator, rejecting convention started early. In this episode, Michelle shares the pivotal moment her entrepreneurial parents told her they didn't believe in university and wouldn't pay for it, advising her to “go work somewhere and learn something practical" instead.This bold rejection of a standard path led her to a year in Australia, taking jobs from barista to marketer to working on a camel farm. That experience taught her to be agile and fail forward —a lesson that would define her career.Michelle walks us through the rollercoaster of entrepreneurship, including the "trough of sorrow". She reveals how the catastrophic Silicon Valley Bank crash in 2023 became the catalyst for her biggest pivot: creating the "Future of Finance Masterclass."Join us to learn how to ride the highs and lows of any Bold Move journey and find the courage to fail forward.Love this episode? There's a whole community of Bold Movers over on Substack. Join us and build your bold moves muscle with us! https://kristenrocco.substack.comConnect with host Kristen RoccoSubstack: kristenrocco.substack.comLinkedIn: /kristenroccoInstagram: @kristenroccoConnect with Guest Michelle BeyoOn LinkedIn: https://www.linkedin.com/in/michellebeyo/Get a discount on Michelle’s “Future of Finance Masterclass” with code: BoldMoves25 https://www.finavatorfuturefinancemasterclass.com/offers/moerwgYe?coupon_code=BOLDMOVES25

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