Apply for the Bold Moves Mastermind HERE!

Learn more about the Bold Moves Mastermind HERE!

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Today’s guests have walked completely different professional paths, but when it comes to career transitions, they arrived at the exact same midlife career crossroads.

With over 15 years in global talent management—leading initiatives across powerhouse brands like McDonald's, Cigna, and Randstad—Kathryne Fliman has built an enviable, high-performing career. Yet, as she approached her 40th birthday, she realized she was caught in a pattern of people-pleasing, putting corporate expectations and everyone else’s needs ahead of her own happiness.

Jen Phillips April was on a completely different trajectory, running a successful B2B content marketing business. But when introducing herself at events as a writer, she noticed the excitement was gone. She was tired of taking one-off writing assignments and craved higher-level strategy work.

Though Kathryne and Jen have different professional backgrounds, they entered the Bold Moves Mastermind facing the same crossroads: unsure of where to go next, but knowing career transitions were the only way forward.

Kathryne and Jen join host Kristen Rocco to discuss how they went from being stuck in a career that no longer fit to discovering and making their bold move. In this episode on navigating career transitions, find out:

• Why they joined the Bold Moves Mastermind
• How they gained clarity on their next career move
• Beliefs they had to unlearn before they could make their bold move
• Breakthroughs they experienced while working through the Bold Moves Method
• The strategic bold moves they made after completing the Mastermind

Connect w/ Host Kristen Rocco

Are you at a career crossroads and ready for what’s next? Map out your next move with confidence—with women who get exactly where you are because they’re right there too.

• Apply for the Bold Moves Mastermind HERE!
• Subscribe to the Newsletter
• Follow me on Instagram
• Let’s connect on LinkedIn

Connect w/ Guest Jen Phillips April

• Connect on LinkedIn
• Subscribe to Jen’s newsletter
• Try Jen’s GPT

Connect w/ Guest Kathryn Fliman

• Connect on LinkedIn

Episode Resources

Book Rec: I Love Me More by Jenna Banks

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.

Rate & Review

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.