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

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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 bold move, transitioning from fractional marketing consulting in her solo business to an in-house role where she’s leading the full marketing function from A to Z.

She’s made the leap, and now it’s game time. How does she keep her bold vision in focus?

Reflecting on our conversation, it struck me that Sherehan laid out a universal playbook for the first 90 days of any bold move, whether you're in a corporate role, an entrepreneur, or on a personal journey.

In this episode, you’ll discover:

• The foundational framework that elevates her vision: “Learn, Plan, Do.” It’s a roadmap to guide clarity, focus, and decisions
• Why true boldness is about delivering value, not always being polarizing.
• How Sherehan's commitment to upskilling guides her to new bold thinking and ideas
• The mindset you need to keep the momentum going

And lots more, so tune in now!

Did you hear our big announcement? I'm so excited to officially launch our new community and resource hub, The Bold Moves Substack channel! This is where we’ll connect, support, and elevate each other as we navigate our bold moves together! Join me and over 100 other Bold Movers there: https://kristenrocco.substack.com/

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with Guest Sherehan Ross

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

Take Sherehan’s course on “Using AI to Create Buyer Personas”: https://www.linkedin.com/learning/using-ai-to-develop-buyer-personas

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 bold move, wondering, “Okay… what now?” “How do I navigate my bold move now?”

That feeling is why, in this season, we’re going deeper. We're talking about how to build and maintain the momentum that keeps you going when the initial excitement fades and the real work begins.

In this season premiere, I’m sharing the powerful mindset for keeping your momentum going when you’re in the thick of it: the decision to Rise to the Occasion.

I’m also taking you behind the mic to share how I’ve been applying this framework in my own business—from navigating a new collaboration to leveling up my own skills to meet my ambitions.

Tune in to discover the three-part framework for rising to the occasion in your bold move!

In this episode, you’ll learn:

• How to apply a 3-part framework for Rising to the Occasion to keep your momentum going inside your bold move
• Why preparedness is the thing that helps you overcome self-doubt.
• How to put fear in the passenger seat to drive closer toward your goals
• Why embracing a growth mindset is more powerful than waiting for perfection.

PLUS, a huge announcement! I'm so excited to officially launch our new community and resource hub, The Bold Moves Substack channel! This is where we’ll connect, support, and elevate each other as we navigate our bold moves together!

If you’re dreaming of, planning, or already navigating your bold move and need the tools and community to keep going, this episode is your starting point!

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

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.

But that’s not all. Stick around to the end to hear about the exciting ‘what’s next!’ for the Bold Moves: How Did You Know podcast. I’m asking a brand new question as we head into Season 4!

In This Episode, I Reflected on the Biggest Lessons From:

• Author Andrea Bartz and her episode “Just Write Already!” (Jan 28, 2025)
• Business owner Scott Merritt and his episode “Laid off? Low job satisfaction? Facing a career setback? Second Act Careers Help You Find Your Purpose (Feb. 11, 2025)
• Leadership Strategist Sarah Schneider and her episode “Why You Need to Shake Up Your Identity to Make a Bold Move” (Feb. 25, 2025)
• Creator Mary McGreevy of her episode “Top Tips from Living a Bold Life…from Dead People!” (March 11, 2025)
• Me, your Host and Business Owner, Kristen Rocco of my episode “A Bold Mindset Is Everything: 5 Mindset Shifts for Success That Changed My Life” (March 25)
• Activist Sandy Rosenthal of her episode “Exposing the Hurricane Katrina Levee Cover-Up” (April 8, 2025)
• Author and Business Owner Sarah Alaimo of her episode “This Is Way More Than a Sobriety Story” (April 22, 2025)
• NICU Family Support Coordinator Jenna Kolodziejczak of her episode “How Jenna Landed Her Dream Job with the Bold Moves Recipe” (May 20, 2025)
• Leadership Coach Robyn Woods of her episode “Your Blueprint for Pivoting to Your Bold Move with Intention, Clarity, and Courage” (June 3, 2025)

Love the Show? Support My Bold Move!

This podcast is a one-woman production, driven by my deep passion for championing bold moves and helping you see your greatest potential. If these stories have inspired you, here are two simple ways you can support the show—and they mean the world!

1. Leave a Rating & Review: For an independent show, your rating and review are the most powerful way to help strengthen this show. It takes just 30 seconds and helps others discover these Bold Moves conversations.
2. Follow for Season 4: Hit the "Follow" or "Subscribe" button in your podcast app to get notified the moment the new season drops. You won't want to miss what's next!

See you in Season 4!

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

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 navigate change with intention, clarity, and courage. In this episode, she introduces us to her powerful concept of Pivot Leadership.

Tune in to discover:

• Robyn's personal pivot journey and the surprising realization that stopped her from pursuing what seemed like the obvious next step.
• The common obstacles and fears that hold so many of us back from making a pivot, even when we feel that visceral pull.
• What "Pivot Leadership" means and how it transforms a simple change into an act of intentionality and ownership.
• Robyn’s four core pivot points – "It's Not Working," "Ready for a Change," "Health Impact," and "New Opportunities." We break each one down with personal stories (I share some of my own "how did you know" moments here too!) to help you use them as an evaluation tool for your journey.
• Answers to YOUR questions about pivots:
  • How can you actually weave pivots into your life?
  • How do you better listen to that "unsettling feeling" and know when it's time to take action?
  • The game-changing difference between "supporters" and "elevators" for your pivots, and the best way to activate both

If you're ready to understand when to pivot on a deeper level and lead yourself towards your next bold move, this conversation with Robyn is for you! Robyn offers actionable advice and thought-provoking questions to help you move from simply experiencing a pivot to truly leading it.

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 Robyn Woods

Website: https://wineandmastermind.com/

linkedin.com/in/robynwoodshr/

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 hardship; it's a masterclass in reinvention using the Bold Moves Recipe: Desire, Who, and Action. Listen as Jenna reveals how she moved from a place of deep personal struggle and "survival mode" to rediscovering her purpose. You'll hear how a persistent Desire to help others in similar situations began to take root, how she found her Who through crucial support and connections, and the brave Action steps she took – from therapy and volunteering to strategically re-entering the workforce.

If you're curious about how to turn life's biggest challenges into fuel for your most purposeful chapter or how the Bold Moves Recipe works in action, this episode is a must-listen. Jenna’s journey to her dream job supporting NICU families is proof that it’s possible.

If you are ready for a change, ready to say goodbye to the doubts that keep your dreams on hold, you’re going to love this episode where Jenna shares how she made her dream job a reality.

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

Episode Resources

Want to dive deeper into the Bold Moves Recipe?

Jenna's story is a powerful illustration of the Bold Moves Recipe in action. If you're inspired to apply this framework to your own life:

• Listen to the full episode where I describe the Bold Moves Recipe and its 3 ingredients in detail while coaching you on how to apply them to your life: https://www.kristenrocco.com/podcast/episode/26c79328/curious-how-to-make-bold-moves-discover-the-bold-moves-recipe
• Share this episode with one person you know who needs support and encouragement in a moment of hardship or change.

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 Jenna Kolodziejczak

Linkedin.com/in/jenna-kolodziejczak-6777732b4

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 your bold moves graduation speech, straight from those who’ve been in the arena — entrepreneurs, creatives, leaders, authors, and advocates. They’ve taken big leaps, faced setbacks, and kept going. Now, they’re sharing what they wish they could’ve told their younger selves about being bold— so you can carry their hard-earned wisdom forward.

Whether you’re a new grad, early in your career, or standing at a midlife crossroads, this one’s for you.

When you're done listening, check out last year’s graduation episode, “A Bold Moves Graduation Speech: What We Wish We Knew About Being Bold Earlier On,” — it’s the perfect companion to double your bold inspiration and fuel your Bold Moves journey even more: https://www.kristenrocco.com/podcast/episode/206e05dc/a-bold-moves-graduation-speech-what-we-wish-we-knew-about-being-bold-earlier-on

Now go out and show the world what you've got! I’m supporting you all the way!

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

Special thanks to all the Bold Move guests featured in this episode:

Kate Grantham, Owner of KIG Events

Imran Syed, Founder & CEO of Hatchproof

Polina Ruvinsky, Founder of HypeHQ

Mikkel Leslie, Founder of A Fulfilled Life Coaching

Julie Stoltman, Founder of Reframe Career & Leadership

Sarah Alaimo, Author and Founder of Elevate Consulting Collective

Kate Weshler, Host of Root to Bloom

Morli Desai, Business Advisor

Scott Merritt, Co-host of Second Act Stories and Founder of Strategic Global Media

Andrea Bartz, Best-selling Author

Sandy Rosenthal, Founder of Levees.org

Sarah Schneider, Leadership Strategist and Executive Coach

Mary McGreevy, Creator of Tips From Dead People

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

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 move of transitioning into a new space and creating a unique chocolate experience for his community in Tecumseh, Michigan.

Matt explains:

✔️ How he and his wife turned their chocolate factory into a community hub with unique experiences.

✔️ The challenge of balancing customer feedback with maintaining your vision.

✔️ How offering ice cream unexpectedly boosted foot traffic and customer loyalty.

✔️ His advice for entrepreneurs one year later.

Don't forget to check out Matt's original episode titled "Building a Chocolate Factory with Matt Cross, Co-Founder of Harvest Chocolate."

Connect with host Kristen Rocco

Join Bold Moves Podcast Club: https://www.kristenrocco.com/bold-moves-podcast-club

Website: kristenrocco.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with guest Matt Cross

Website: https://harvestcraftchocolate.com

Instagram: https://instagram.com/harvestcraftchocolate

Facebook: https://www.facebook.com/HarvestCraftChocolate

Linkedin https://www.linkedin.com/in/matt-cross-/

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 become the best version of yourself.

Even if alcohol has never been your struggle, you’ll walk away from this conversation with a deeper understanding of what it means to make bold, life-altering changes, to face your truth, and to pursue a life aligned with who you really are.

Sarah shares what it was like to navigate the high expectations of being a “good girl,” the hidden pain behind a polished exterior, and the moment she realized she could no longer keep living the same story. Her vulnerability, honesty, and clarity offer so much more than a recovery roadmap—they’re a guide to personal transformation.

“I didn’t see anybody out there who looked like me who was speaking out about the process,” Sarah says. “And I just decided that there are a lot of other ‘good girls’ out there who might be afraid to start that journey and need to see someone who looks like them or has a similar story.”

Sarah proves that when you stop hiding, you start truly living, and she invites all of us to pause, reflect, and ask: What would it look like to live more honestly?

Like this episode? There's a whole community of Bold Movers over on Substack. Join us and build your bold moves muscle with us! kristenrocco.substack.com

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with guest Sarah Alaimo

Website: https://elevateconsultingcollective.com/

Instagram: @sarahdalaimo

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 the truth.

Sandy's efforts to expose the cover-up and uncover the truth have led to significant changes in levee flood protection systems and educational initiatives to ensure such engineering failures never happen again. The episode delves into Sandy's bold move of exposing a historic cover-up, the hurdles she overcame, and her continued fight to ensure this never happens again.

Tune in to discover:

✅ Sandy Rosenthal's work and bold moves as an activist and author

✅ The levee failures of Hurricane Katrina and the government cover-up

✅ The emotional toll of Hurricane Katrina

✅ The grassroots campaign sparked by Sandy and the early days of Levees.org

✅ How Sandy rallied the community–and the nation

✅ How Sandy faced government opposition

✅ Sandy's resilience to continue fighting for the truth and change

✅ What Sandy knows today about being bold she wishes she knew earlier on

Like this episode? There's a whole community of Bold Movers over on Substack. Join us and build your bold moves muscle with us! kristenrocco.substack.com

Connect with host Kristen Rocco

Substack: kristenrocco.substack.com

LinkedIn: /kristenrocco

Instagram: @kristenrocco

Connect with guest Sandy Rosenthal

https://levees.org/

sandyrosenthal.net

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 the ladder, and getting recognition, but something still felt off. I was searching for more.

Fast forward to 2025, and everything has changed. The difference? A bold mindset. Because mindset is everything when it comes to writing your own story and creating success.

What I didn’t realize then that I do now is that you need to embrace key mindset shifts for success that allow you to push past fear, uncertainty, and self-doubt to keep pursuing your bold move.

In this 50th-episode celebration, I take you the behind-the-scenes of how these 5 powerful mindset shifts for success have changed my life:

✅ Fear of Uncertainty → Trust in Yourself

✅ Fear of Failure → Freedom

✅ From Comfort → Stretching Your Limits

✅ From Playing Small → Owning Your Value

✅ From Waiting for Permission → Stepping into Your Power

Tune in to hear the behind-the-scenes of how these mindset shifts unlocked new opportunities, growth, and success.

If you're ready to build a bold mindset for success, this episode is for you!

Like 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

Take the listener survey: https://docs.google.com/forms/d/e/1FAIpQLSdgwwN2dxCqdnGSgIhpiZagKGXdBVEWi4vaoYRXrx_O6e83LQ/viewform?usp=sf_link