Jeff Ragovin: “You don’t need to know the next thing”
Step Into Next
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...
info_outline
The Liminal Space: Easing Into What’s Next
Step Into 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...
info_outline
The Messy Middle & Normalizing the Struggle
Step Into Next
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...
info_outline
Our Secret Sauce: The Process for Writing and Working Together
Step Into Next
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...
info_outline
The Importance of Finding Your Voice and Owning Your Story
Step Into Next
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...
info_outline
Our Origin Story: How Two Entrepreneurs Became Unlikely Writing Partners
Step Into Next
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...
info_outlineIn 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.