On ‘Step Into Next’ Leanne and Helaine love to cover what they call the “liminal” space; and that in-between can mean a LOT of different things, and this episode certainly proves that.

In this one, they unpack what it really means to trust “divine timing” (without bypassing grief, frustration, or real-world messiness). They also (somewhat surprisingly!) explore spirituality as a practical tool for letting go of control, why “everything happens for a reason” can be harmful in certain moments, and how surrender looks different depending on where you are in your journey.

The conversation moves through:

• Navigating the uncomfortable gray space between one identity and the next

• The space in between after breakups/divorce, selling a company, or retiring from a pro sport career

• Having confidence in any gray area 

• Helping close friends navigate the space in between without being pushy or insensitive (and why Mel Robbins’ “Let Them” paradigm can be a powerful tool!)

• Why comparison (especially via social media) can derail your sense of self

• Defining what divine timing means to us and reframing it in a way that doesn’t dismiss real loss or pain

• Why imposter syndrome may be less of a personal flaw (and is it really a “syndrome”?!) and more of a systemic issue

• How women are conditioned to doubt themselves in business, leadership, and life

• If the the phrase “everything happen for a reason” is true
  

  This episode is for anyone who feels behind, uncertain, or questioning whether they’re doing life “right” while simultaneously navigating power structures that weren’t necessarily  built for them.

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.

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.

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. 

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.

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.

Helaine and Leanne kick off the series by looking back at how ambition, burnout, and trust shaped their unlikely partnership. It’s a real talk about what happens when one chapter ends, another begins, and you’re still figuring out who you are in between.

From a legendary snack bag to legacy itself, Helene and Leanne unpack how finding your why helps you find your voice.

Highlights:

• Why purpose, not polish, drives creative work
• How writing a book became identity therapy
• What to share (and protect) when telling your story