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

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

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.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. 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/genevievedozier

Website: https://warpaintconsulting.com/

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

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 Trajectify

1:52 - Personal Risk-Taking Leads to His Boldest Move

7:44 - Mike's Professional Career

15:27 - The Catalytic Moment that Changed Everything

16:47 - Vulnerability Requires Courage

25:11 - Sunk Cost Fallacy

33:24 - If Not Now, When?

Join the Bold Moves Community

And 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.com

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

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.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. 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.com

Blue Balloon Songwriting School: blueballoonschool.com

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

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.com

Connect with Guest Erin Fortin:

• Website: erinfortinphotography.com
• Instagram: @erinfortinphoto

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Mentioned 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

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.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. 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 Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with Guest Simone Knego

Website: simoneknego.com

Book: Real Confidence: A Simple Guide to Go from Unsure to Unshakeable at realconfidencebook.com

Simone's reflection on how climbing Mount Kilimanjaro changed her life: https://simoneknego.com/how-climbing-a-mountain-can-change-your-life/

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.com

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with Co-host Tyler Hakes

On LinkedIn: https://www.linkedin.com/in/tyler-hakes/

Read our Authority Moat Model Transformation Narrative: https://www.yesoptimist.com/authority-moat-model/

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.com

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with Guest Michelle Beyo

On 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

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 presidents. Kelly's work profoundly shaped US policy, earning her the National Intelligence Meritorious Unit citation twice. More than an intelligence strategist, Kelly bridges her high-stakes career with a deep physical intuition honed through years of martial arts and practicing in high-stakes scenarios at the CIA.

Kelly is one of the most exceptional storytellers I’ve met, and these are juicy! She shares how she got recruited to the CIA (does the gray man actually exist?), her boldest, hallmark moment leading to historic changes at the Agency, the myths surrounding the CIA, and how she initiated significant wellness programs within the Agency to cope with the psychological toll of her role.

Kelly teaches us:

• How to remain anchored in your core values while navigating a demanding career and making bold moves.
• A practical technique you can use today for maintaining your calm in high-stress situations.
• How to tap into body intelligence for decision-making around your bold move.
• Why – not how – you should make a bold move.

Push play now to be debriefed on bold moves from a former CIA analyst. I promise, you can't miss this one!

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with Guest Kelly McGannon

On LinkedIn: https://www.linkedin.com/in/kellymcgannon/

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.

When Ashley applied for a new director of Gen AI role at her organization, this is exactly what she confronted: an interesting job description in an emerging space that no one in her organization–or anywhere else for that matter–had ever done before.

When you make your bold move, you’re going to be the first in some capacity. The steps to achieve your vision will look blurry.

I asked Ashley how she is navigating being the first to help us all in our Bold Move firsts. From keeping a "kudos folder" to overcome bad days to figuring out how to overcome her stakeholders’ hesitations about a new technology, she shares practices you can embrace to help you confidently lead and navigate the path when no one has gone before you.

Ashley teaches us her tips for:

• Overcoming imposter syndrome.
• What to do when you don’t have all the answers.
• How to break through the status quo to influence change
• And much more

This episode is a powerful two-for-one. You'll get actionable advice on the skills needed to be first in your bold move, alongside critical insights into AI from one of the industry's foremost experts. Ashley shares the same expertise she's brought to stages at Adobe Summit, The AI Leaders Forum, Boston University, and Vanguard, making this a can't-miss conversation.

Stay tuned until the end for her rapid-fire answers to your pressing questions about AI:

• Where do you see AI being the most effective? What problems is it solving for businesses?
• What are AI’s limitations?
• What are the AI courses you recommend?
• What’s the predictive capability of gen AI?
• What’s Agentic AI?

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.com

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with Guest Ashley Cheretes

On LinkedIn: https://www.linkedin.com/in/ashleycheretes/