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-mastermindAnd let’s make your bold move happen!Connect w/ Host Kristen RoccoSubscribe to the Bold Moves NewsletterFollow me on InstagramLet’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.Rate & ReviewComplete 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 NiddaWebsite: with-helen.comBuy the Book: Closing the Fulfillment Gap: How to Find the Work Life You WantSubscribe to Career Joy With Helen:Follow Helen on LinkedInConnect w/ Host Kristen RoccoSubscribe to the Bold Moves NewsletterWatch this episode on YouTubeFollow me on InstagramLet’s connect on LinkedInBold 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.comBold 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_treyLinkedIn: Trey TolerConnect w/ Host Kristen RoccoSubstack: kristenrocco.substack.comInstagram: @kristenroccoYouTube: 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.comConnect with Guest Dr. Sarah BergWeb: www.selfority.com.Substack: https://sarahbergmd.substack.com/IG: https://www.instagram.com/selfority/YouTube: https://www.youtube.com/@SelforityConnect w/ Host Kristen RoccoSubstack: kristenrocco.substack.comYouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcastIG: @kristenroccoLinkedIn: /kristenroccoLove 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.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. Join a community of women all making bold moves right alongside you.Connect w/ Kanika Chadda-Gupta:Instagram: @ kanikachaddagupta thatstotalmomsense.comConnect w/ Host Kristen RoccoSubstack: kristenrocco.substack.comYouTube: https://www.youtube.com/@BoldMovesHowDidYouKnowPodcastLove 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."