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

I got laid off at 39, and suddenly found myself at a midlife career crossroads. Instead of rushing to send out another resume, I asked myself a pivotal question that became the foundation for my bold move: What do I want?

Usually, I bring on incredible guests to share how they made their bold moves. But today, I’m going off-script.

I’m opening the next cohort of the Bold Moves Mastermind, and I wanted to take a moment—just you and me—to pull back the curtain on why I built this experience, share pivotal stories about my own career change that I haven't talked much about on the show, and walk you through the exact Bold Moves Method we use to clarify and plan your bold move so you can become the author of your own story.

If you’ve been feeling like you did everything you were "supposed" to do—your life looks successful on the outside, but inside you don’t feel fulfilled and you're craving a career change or next chapter—I’ve been right where you are.

In this intimate solo episode, I share:

• The moment I got laid off—and the single question that changed everything: What do I want? It sounds simple, but it was the first time I put my own needs before my employer's—and it forced me to stop outsourcing my worth to a title.
• The childhood TV dream I tucked away for 15 years while holding the microphone for everyone else's ideas instead of my own.
• The 3-part Bold Moves Method: I codified after interviewing 70+ Bold Movers to get your "someday" dream off the back burner and into action to navigate a career change with confidence:
  • YOU: Unpacking your midlife crossroads, silencing your inner critic, and stepping into your story as the main character.
  • WHO: Building your "Bold Moves Advisory Board," surrounding yourself with Supporters, Elevators, Expanders, and Community so you never make a bold move in isolation.
  • DO: Using the Aligned Action Pyramid to build confidence through small micro-actions, without needing to blow up your life or quit your job tomorrow.

Ready to take your bold move off of the “someday” list?

Leanr about the Bold Moves Mastermind right here: https://kristenrocco.substack.com/p/bold-moves-mastermind

And let’s make your bold move happen!

Connect w/ Host Kristen Rocco

• Subscribe to the Bold Moves Newsletter
• Follow me on Instagram
• Let’s connect on LinkedIn

Exciting Announcement! Learn about the Bold Moves Mastermind & Apply Here!

Are you unfulfilled in your career—even when you’re advancing and growing by landing promotions, earning advanced degrees, and taking on new projects? You feel stuck, undervalued, and bored. If that sounds familiar, you are experiencing what my guest calls the "fulfillment gap," and it might be time for a midlife career change.

Dr. Helen Krug von Nidda is a 20+ year HR veteran and a powerhouse in leadership development and career empowerment for women. She joins host Kristen Rocco to share career fulfillment research and introduce her MOVE framework to help women break through barriers and design a career aligned with their true life goals from her new book, Closing the Fulfillment Gap. She shares practical career change tips to help you bridge the gap between where you are and the career fulfillment you deserve.

Tune in to spark the ideas that will lead you toward a more fulfilling career.

• Why modern choices, remote flexibility, and promotions haven't made midlife women any happier than prior generations.
• How Autonomy, Relatedness, and Competence drive long-term career fulfillment more than compensation or extrinsic perks.
• How staying stuck in the comparison trap, running at max capacity, and overcommitting prevent women from answering what they actually want their lives to look like.
• A breakdown of Dr. Helen's research-backed MOVE framework—Motivation, Opportunities, Vision, and Encouraging Community.
• Discover whether you are a Seeker (pursuing authenticity), a Navigator (seeking balance), or a Venturer (ready for a high-challenge bold move) based on your current season of life.

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Complete this fun prompt to leave us a review today: "Joy looks like this for me: [fill in the blank]"

Connect with Guest Helen Krug von Nidda

• Website: with-helen.com
• Buy the Book: Closing the Fulfillment Gap: How to Find the Work Life You Want
• Subscribe to Career Joy With Helen:
• Follow Helen on LinkedIn

Connect w/ Host Kristen Rocco

• Subscribe to the Bold Moves Newsletter
• Watch this episode on YouTube
• Follow me on Instagram
• Let’s connect on LinkedIn

Bold Moves: How Did You Know? is for women at a midlife crossroads ready to make a career pivot, launch a business, or design a life on their own terms. Each episode delivers the real stories and bold micro-actions you need to move beyond the midlife crisis, shed identities that no longer fit, and step into your Midlife Click.

If you're feeling stuck in an identity that no longer fits and ready to grow into the best version of you, today's guest is living proof of what happens when you finally stop performing and start authoring your story from a place of authenticity and conscious choice.

Host Kristen Rocco interviews Trey Toler—Atlanta-based author, keynote speaker, and stand-up comedian—to unpack his powerful memoir, Good Damage. For years, Trey hid behind a polished mask and the role of the hilarious class clown to shield himself from the pain of his mother’s chronic illness and the secret of his sexuality. After her sudden death sent him spiraling into self-destructive patterns, Trey realized that while you can't control what happens to you, you are solely responsible for choosing who you become next. Through a profound shift in perspective, he stopped circling his trauma like a vulture and chose to live as a hummingbird—actively seeking life, color, and purpose.

🎧 You’re going to get immersed in Trey’s unbelievable transformation story and learn how he picked himself up out of the rubble to become the best version of himself, with plenty of comedic relief along the way:

• Vulture vs. Hummingbird: The powerful metaphor of hunting for decay versus actively searching for color, hope, and purpose.
• The Trap of the Performance: How keeping up a polished exterior hides your pain and prevents genuine healing and growth.
• Unmasking & Authenticity: Navigating the vulnerability of coming out and what it takes to stand fully rooted in your truth.
• The Illusion of an External Fix: Realizing that looking outward won't "fix" you until you do the internal work required to transform from within.
• Your Zone of Genius: How stepping into your natural gifts allows you to convert past pain into authentic connection and light.

Join the Bold Moves Newsletter here: kristenrocco.substack.com

Bold Moves: How Did You Know? is for anyone 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.

Connect w/ Guest Trey Toler:

• Memoir: Good Damage (Available on Amazon, Barnes & Noble, and everywhere books are sold)
• Instagram & TikTok: @toler_the_trey
• LinkedIn: Trey Toler

Connect w/ Host Kristen Rocco

• Substack: kristenrocco.substack.com
• Instagram: @kristenrocco
• YouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcast

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!

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."

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."

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!

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?

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."

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