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

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 share...

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 fac...

UPDATE: Host Kristen Rocco is bringing together the Bold Moves community for a Podcast Club Power Hour to discuss this episode on July 8, 2026. Join us: https://www.kristenrocco.com/event-details/bold-moves-podcast-club-power-hour 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...

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...

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...

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 pr...

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...

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 i...

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 stro...

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 thes...

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 yo...

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...

Imagine your workday begins by delivering the world's most sensitive intelligence directly to the president of the United States. Sounds like a job for fictional characters like Jack Ryan, Carrie Mathieson (Homeland), ​​Owen Hendricks (The Recruit). But no. That was the reality for my guest, Kelly McGannon, during her 20-year career with the CIA. She delivered sensitive intelligence to two US pres...

We're live on Substack! Join us: kristenrocco.substack.com Being the first is bold. No one has gone before you. There is no playbook. You are charting the course, sometimes confidently because of your immense conviction and sometimes courageously because your gut sense is leading you. Being the first… that’s the theme of this episode with Ashley Cheretes, Director of Gen AI at Prudential Financial...

We're live on Substack! Join us: kristenrocco.substack.com Bold Movers, I am excited for you to meet Sherehan Ross, VP of Marketing at Modus Planning in this episode! As we transition into exploring a new question this season, how do you continue to be bold inside of your bold move, I knew Sherehan would be the perfect guest to kick off this season’s interview series! She has just started her next...

We're live on Substack! Join us: kristenrocco.substack.com Hey Bold Mover! It’s your host, Kristen Rocco, and welcome to the Season 4 premiere! For three seasons, we’ve asked the question, “How did you know?” We focused on the toolkit, characteristics, and mindset it takes to make a bold move. But what happens after ? What happens when you find yourself in the messy, unglamorous middle of your bol...

For three seasons, we've been on a journey to uncover what it takes to make a bold move–and this season sure did deliver! We heard from an incredible lineup of authors, activists, leadership strategists, business owners, and creators who pulled back the curtain on their most pivotal moments. In the season 3 recap, I’m reflecting on those moments and lessons from each of this season’s Bold Movers....

Do you feel that undeniable nudge for a change, a sense that you're ready for something different but aren't quite sure how to take the lead on that internal call to pivot? It's a common crossroads, and one my guest, Robyn Woods, helps people master. As a Leadership Development Consultant and the visionary founder of Wine & Mastermind, Robyn specializes in equipping leaders like you and me to...

Ever wonder how to navigate profound life changes and come out stronger? This week on Bold Moves: How Did You Know? recorded live and in person, my dear friend Jenna Kolodziejczak shares her incredible story of doing just that. After the traumatic premature birth of her twin sons and a grueling NICU experience, Jenna faced a total loss of her old life and identity. But this isn't just a story of h...

Today’s episode is a special one — and something of a tradition now. Around this time last year, I created a graduation-themed episode featuring powerful answers to the question I always ask my guests: “What do you know today about being bold that you wish you knew earlier on?” It became one of the most shared episodes — and it stuck with me. So this year, I'm bringing it back! This episode is you...

In this special 'Where Are They Now' edition of the Bold Moves: How Did You Know podcast, I reunited with Matt Cross, Co-Founder of Harvest Chocolate. Previously featured in episode 27, Matt shares the progress of his Bold Moves entrepreneurial journey over the past year. In this check-in episode, we follow up on his journey and explore the latest milestones of his business, including the bold mov...

In this powerful episode, host Kristen Rocco sits down with Sarah Alaimo, strategic fractional HR leader at Elevate Consulting Collective and author of the memoir Pearls and Probation: Adventures of an Alcoholic Good Girl . Sarah opens up about her deeply personal journey to sobriety, but this isn’t just a story about addiction—it's a story about courage, identity, reinvention, and choosing to bec...

In this episode, host Kristen Rocco introduces you to Sandy Rosenthal, an activist, author, and founder of Levees.org . Sandy shares her journey of uncovering the levee engineering failures that led to catastrophic flooding in New Orleans during Hurricane Katrina in 2005. She discusses how she became a vocal critic of the U.S. Army Corps of Engineers and the challenges she faced in advocating for...

Hey Bold Mover! It’s your host, Kristen Rocco. Today’s episode is extra special. Not just because it’s the 50th episode, but because launching this podcast marks a turning point in my life. It was the moment I let my curiosity lead me to my next bold move. Back then, I was searching for answers—why, despite my high performance, did I keep hitting roadblocks? I was achieving milestones, climbing th...

In this special 'Where Are They Now' edition of the Bold Moves: How Did You Know podcast, I reconnect with Ang Barnard, who was originally featured in episode four. Ang shares her journey over the past two years, including becoming a new mother, giving birth at home, extensive traveling, and her continued passion for speaking engagements on energy-shifting communication strategies. She also talks...