Step Into Next

Helaine Knapp & Leanne Shear
  • 5.0 (59)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

You know that unsettling in-between space after one big chapter ends and before the next one begins? That's where we live. Step Into Next is about navigating the sometimes messy and maddening but also always exciting space "in between," in between, with honesty, humor, and heart. Hosted by Leanne Shear and Helaine Knapp, two entrepreneurs who've learned that growth doesn't stop at the finish line.

Episodes

  1. 5D AGO · VIDEO

    What's Next Doesn't Have to Be the Next Big Thing!

    After one big chapter ends, the question everyone asks is: "So… what's next?" But what if what's next doesn't have to be the next big thing? In this episode of Step Into Next, Helaine and Leanne get honest about the in-between season, that liminal space after you've built something meaningful, closed a chapter, or hit a major milestone, and you're not quite sure what comes next. They talk about: -Why pressure, expectations, and identity can make "figuring out what's next" feel overwhelming -The difference between control vs. surrender (and how The Surrender Experiment by Michael Singer reshaped how they think about growth) -Barack Obama's idea of asking "What's my next highest and best use?" - and why that question is both clarifying and stressful -Letting go of doing things just because you're good at them -The slow, intentional process of unstitching your identity from a former role, company, or achievement -Why once you've experienced flow and alignment, it's hard to settle for anything less Along the way, they share real-time stories, from post-LASIK realizations and dating metaphors to pent-up creative energy, retiring from past identities, and learning how to sit with uncertainty without rushing to fill it. If you're navigating a career transition, life pivot, entrepreneurial pause, or personal reinvention - and wondering why the next step feels so unclear, this conversation is for you. Because sometimes, your next highest and best use… is exactly where you are right now.

    19 min

  2. JAN 13 · VIDEO

    Jeff Ragovin: "You don't need to know the next thing"

    We're so excited to welcome our first guest, Jeff Ragovin, to Step Into Next.  Jeff is a longtime friend and mentor to Helaine, an entrepreneur behind $1B+ in exits, and someone whose career has taken a lot of unexpected turns.  Including starting out in meteorology and working as a weatherman…yes, actually.  From Buddy Media to Salesforce and beyond, Jeff's path has been anything but linear…and that's one of the keys to his success! In this episode… Jeff shares his journey through tech, leadership, and multiple reinventions What it really feels like to sit in the in-between after big wins Knowing a chapter is ending long before you're ready to leave it Staying in roles longer than expected out of responsibility and integrity Untangling your identity from your work during transitions How curiosity and passion projects, like Bounty Uncharted, open new doors Why believing you can figure it out matters more than having a clear plan If you're in a moment of transition and feeling unsure about what's next, this conversation offers reassurance without pretending it's easy. Jeff's story is a reminder that uncertainty shows up at every stage - and that sometimes the next chapter starts by following your passion, being open to wild opportunities, and trusting yourself one step at a time.

    37 min

  3. JAN 6 · VIDEO

    The Liminal Space: Easing Into What's Next

    January is often framed as a fresh start, but for many of us it feels more like an in-between.  The holidays are over, routines haven't fully returned, big plans aren't locked in yet, and motivation comes in waves. Instead of rushing to define the year or forcing clarity, this episode is about staying in the liminal space a little longer. The space in  between what ended and what's still forming.  In this conversation we'll talk about: You are not behind - you're right where you need to be Letting momentum be subtle, uneven, and still real Releasing pressure around resolutions and timelines Trusting that foundations matter more than outcomes If you're moving a little slower or giving yourself permission to take things one step at a time, this episode is for you.

    19 min

  4. 12/09/2025 · VIDEO

    The Messy Middle & Normalizing the Struggle

    In this episode, Helaine and Leanne pull back the curtain on what they call "the struggle" – those seasons where self doubt, burnout, and rejection are loud, but you keep going anyway. Drawing from the real behind the scenes story of writing and publishing Making Waves, they share how their first version of the book didn't sell, the painful feedback that "women don't buy business books," and what it took to completely reengineer the project into an inspirational memoir that actually reflected Helaine's full story. Along the way, they talk about what it means to normalize struggle, why it's okay to be in the struggle but dangerous to become the struggle, and how to keep it at arm's length instead of letting it define you. You'll hear honest conversation about perfectionism, people pleasing, creative collaboration between friends, and the emotional rollercoaster of entrepreneurship, book deals, and big pivots in mid-career and midlife. If you're a woman founder, leader, or professional navigating a career transition and wondering if your setbacks mean you're off track, this one will feel like a deep exhale. In this episode, we cover: What "the struggle" actually looks like in real life and business The difference between sharing your struggle and dwelling in it The rocky path from startup style business book to vulnerable memoir Gender bias in business publishing and why women's stories matter How to hold onto your "why" when the feedback is brutal and the outcome is uncertain Perfect for women entrepreneurs, aspiring authors, and anyone in a messy middle season craving real talk about resilience, reinvention, and writing your next chapter while you're still living it.

    22 min

  5. 12/02/2025 · VIDEO

    Our Secret Sauce: The Process for Writing and Working Together

    What really happens when two women try to build something meaningful together while juggling careers, identity shifts, burnout, and the pressure to have it all figured out? In this episode, Helaine and Leanne pull back the curtain on the messy, funny, and unexpectedly healing process behind writing their book Making Waves and building a creative partnership from the ground up. They talk about what it feels like to work with friends, how to set boundaries without losing the relationship, and why understanding your learning style (verbal, written, or visual) can completely change the way you collaborate. Helaine shares a raw and unfiltered look at a real day in her founder life with investor pressure, media appearances, emotional exhaustion, and the quiet unraveling that pushed her toward storytelling as a form of survival. Leanne reflects on the power of being heard, the trust that comes from say-do integrity, and the belief that collaboration is stronger than competition. If you are navigating a career shift, rebuilding after burnout, or stepping into your next chapter, this conversation offers relatable truths, honest humor, and the reminder that you do not have to figure everything out alone. Themes: • Working with friends and setting boundaries • Burnout, reinvention, and founder honesty • Learning styles and communication • Trust, consistency, and say-do integrity • Collaboration versus competition • Turning chaos into clarity through storytelling A must-listen for women in motion including career shifters, creatives, founders, and anyone figuring out what comes next.

    19 min

  6. 12/02/2025 · VIDEO

    The Importance of Finding Your Voice and Owning Your Story

    In this episode, Helaine and Leanne take a very on-brand detour from an industrial-sized snack bag into the real heart of today's conversation: finding the why behind your voice, your work, and the stories you choose to tell. Through laughter, tangents, vulnerability, and a few questionable tuna-packet moments, they unpack what it really takes to create something meaningful; whether it's a book, a business, or a new chapter of your life. Helaine shares the surprising truth behind writing Making Waves: how she never dreamed of becoming an author, why she said yes anyway, and how the process ended up becoming a form of identity therapy during one of the hardest professional transitions of her career. Together, they explore the deeper reasons we share our stories: to build credibility, to relaunch ourselves after endings, to process what's been hard, and to offer someone else the courage to speak up too. This is a conversation about power, reinvention, creative partnership, and the unexpected clarity that comes when you finally decide to use your voice. If you're navigating a transition, trying to understand your own why, or wondering how to start telling your story, this one will hit home.

    27 min

  7. 12/02/2025 · VIDEO

    Our Origin Story: How Two Entrepreneurs Became Unlikely Writing Partners

    In this first episode, we open the door to the conversations women rarely get to have out loud. The ones about ambition, identity, reinvention, and the quiet pressure to have it all figured out by now. Helaine and Leanne share the real stories behind their own pivots, the lessons they wish they'd learned earlier, and the moments that reshaped how they work, lead, and live. This episode sets the tone for the entire show: honest, elegant, a little whimsical, and grounded in the perspective of women who've built impressive careers and are now asking, okay, what's next? If you're navigating a transition, building something new, or craving a voice that feels like a wiser sister talking you through the hard stuff, this is the place to land. You'll walk away with clarity, reassurance, and a reminder that reinvention is a strength!

    18 min
  • 7 Episodes

5
out of 5
59 Ratings

About

You know that unsettling in-between space after one big chapter ends and before the next one begins? That's where we live. Step Into Next is about navigating the sometimes messy and maddening but also always exciting space "in between," in between, with honesty, humor, and heart. Hosted by Leanne Shear and Helaine Knapp, two entrepreneurs who've learned that growth doesn't stop at the finish line.

Information

  • Creator
    Helaine Knapp & Leanne Shear
  • Years Active
    2025 - 2026
  • Episodes
    7
  • Rating
    Clean
  • Copyright
    © 2025
  • Show Website
    Step Into Next