How Does She Do It All: Kaitlin Becker

When the world sees you as a children’s TV star, they assume your life is all smiles and glitter—and maybe even a private jet. But for Kaitlin Becker, best known for playing Mika, Blippi’s best friend, the reality of single motherhood looked very different behind the scenes. In this intimate and refreshingly honest episode, Kaitlin opens up to Olivia about choosing to end her marriage in 2021, navigating the guilt and relief that comes with that decision, and how co-parenting just one street away from her ex shaped her new normal.

With the hustle of auditions, voiceover gigs, and writing new shows, Kaitlin shares what it’s like to entertain other people’s children while missing her own—and the emotional gymnastics required to keep showing up both as a performer and a present parent. She speaks candidly about the disconnect between public perception and personal reality, especially as a single mom in the entertainment industry. The internet may think she’s a millionaire, but the truth is much messier, more human, and deeply relatable.

Through it all, Kaitlin finds joy in the quiet moments—playing the piano alone, sneaking off to Broadway shows solo, and bonding deeply with her son, Everett. She reminds us that single motherhood isn’t a story of lack—it’s a story of freedom, creativity, resilience, and radical self-trust. If you've ever wondered what it really looks like to grow up alongside your child, this episode is your invitation in.

How Does She Do It All: Joy Mangano

The night Joy Mangano’s husband walked out the door, she sank to the floor and cried until morning. But by sunrise, a new woman had risen—one who would go on to transform not only her own life, but an entire industry. In this emotionally charged episode, Olivia Howell sits down with Joy to explore what it really takes to rebuild after heartbreak, raise three children as a single mom, and pursue a dream when everything is stacked against you.

With brutal honesty and signature warmth, Joy opens up about growing up in a traditional Italian household, suppressing her inventive nature to fit into expectations, and the moment she chose courage over comfort. As she tells it, there was no roadmap—only a burning instinct that she could do more, be more, and give more to her children by betting on herself. From experimenting with her earliest inventions in the back of her father’s auto body shop to launching the Miracle Mop on QVC, Joy shares how she created a new life not just out of necessity—but out of vision.

This is more than a story about entrepreneurship. It’s about legacy, motherhood, grit, and the quiet magic of building a bond so strong that her children now stand beside her in business and life. Joy also shares her latest chapter as co-founder of CleanBoss, a cutting-edge cleaning brand created with global superstar Pitbull. CleanBoss offers powerful, non-toxic, plant-based cleaning products—including their best-selling botanical disinfectant and zero-mess laundry sheets—all designed to make everyday cleaning safer, faster, and more effective. With CleanBoss, Joy is once again reinventing how we care for our homes, proving that practicality and innovation can—and should—go hand in hand.

Whether you’re a single mom, an aspiring entrepreneur, or someone at a crossroads, Joy’s story is a reminder that you don’t have to do it all—you just have to start.

How Does She Do It All: Autumn Calabrese

There’s a certain quiet strength in single motherhood that rarely gets the spotlight. In this episode of How Does She Do It All?, Olivia sits down with Autumn Calabrese—fitness icon, entrepreneur, and solo mom—to uncover the real, unfiltered story behind her powerhouse presence. From a two-year-old on her hip and a one-bedroom apartment to launching her 18th at-home fitness program and raising a teenage son, Autumn shares how she rebuilt her life on the other side of divorce—one step, one sweat session, and one deep breath at a time.

Autumn doesn’t sugarcoat the messiness. She opens up about the early days of single parenting, the emotional aftermath of divorce, and the invisible weight of being the default parent, breadwinner, and emotional anchor. But she also shares the tools that carried her through: fierce non-negotiables, nightly check-ins with herself, and a whole lot of grace. With vulnerability and power, she reclaims her story—and reminds us that progress, not perfection, is the path forward.

This conversation is more than a peek behind the curtain. It’s a testament to what’s possible when women refuse to let hardship define them. Autumn’s honesty about burnout, boundaries, and learning to prioritize herself is a lifeline for any mom trying to hold it all together. If you’ve ever wondered how someone does it all—this episode doesn’t just answer the question, it rewrites the entire narrative.

How Does She Do It All: Lisa Easton

When Lisa Easton’s 23-year marriage ended, she thought the hardest part was behind her. But life had more in store: financial devastation, total responsibility for four grown children, and the sudden death of her ex-husband. With no partner to lean on, no safety net, and nowhere to go but her sister’s spare bedroom, Lisa did what many would think impossible—she rebuilt, from the ground up, with little more than belief, discipline, and sheer will.

In this powerful episode, Olivia sits down with Lisa, now the radiant CEO of Millionaire Morning Mamas, to trace the journey from bankruptcy and grief to multi-million-dollar success and personal transformation. Lisa doesn’t sugarcoat a thing—she shares the emotional weight of being a single mom to adult children, the brutal financial truth of post-divorce life, and how she clawed her way back using manifestation, self-care, and a strict morning routine. She reminds us that sometimes the only way out is through, and that women—especially single moms—carry a strength the world rarely acknowledges.

This is an episode about resilience, reinvention, and radical self-trust. Lisa shows us what’s possible when a woman decides to stop waiting for permission and starts betting on herself instead. Whether you’re a single mom in survival mode or just wondering what’s next for your life, Lisa’s story will crack your heart open and fill it with hope.

How Does She Do It All: Olivia Howell

Before Olivia Howell became the host of How Does She Do It All, she was already living the question every single mom silently asks herself: How do I hold all of this? In this special episode, the mic turns toward Olivia as her sister—and co-founder of Fresh Starts—Jenny interviews her about what single motherhood really looks like behind the scenes. With candor, humor, and heart, Olivia reflects on becoming a single mom in 2019, raising two boys through a pandemic, and the emotional labor of parenting solo—even when you were doing it alone long before the title made it official.

Olivia shares the sacred rituals that keep her grounded: morning meditations before the kids wake, walking meetings on a treadmill, and late-night sitcoms with her sons. She doesn’t sugarcoat the hard parts—parenting two deeply feeling, wildly different boys in today’s world takes stamina, self-awareness, and constant reparenting. But she also shares the unexpected joys: quiet dinners with just one kid, deep conversations about consent, and the jazz-like rhythm of their little family of three, playing in sync.

This is an episode about freedom and fatigue, about trading marital chaos for peace in a smaller space, and about how healing can happen in a tiny room with rice cakes, a good sitcom, and your kids beside you. It’s also a gentle reminder that the key to “doing it all” might just be learning to do it differently—with intention, with support, and with the fierce belief that your sacred space is wherever you decide to rebuild it.

How Does She Do It All: Leslie Gray Streeter

When Leslie Gray Streeter became a mother, she never imagined doing it alone. But just two years into parenting, her husband passed away suddenly, and Leslie found herself navigating single motherhood while completing her son's adoption—alone but determined. In the years since, she’s built a life full of morning routines, chickpea-powered meals, late-night homework negotiations, and quiet moments of resilience. In this episode, Leslie opens the door to her world with unflinching honesty, sharp humor, and the kind of wisdom that only comes from surviving the unimaginable and still laughing at your kid’s inability to find the hamper.

Leslie and Olivia dive deep into the realities of solo parenting after loss, from the emotional toll of being the only one who knows where the lunchbox is, to the quiet victory of hiring a house cleaner without guilt. Leslie shares how her village extends beyond her family to include bosses who check in, sisters who show up, and kids’ friends who think she should be on TV game shows. Her story is a powerful reminder that support comes in many forms—and that taking up space as a single mom isn’t just necessary, it’s revolutionary.

Whether she’s reinforcing bedtime boundaries, navigating middle school drama, or just trying to watch White Lotus without being interrupted, Leslie shows us the messy, beautiful truth about what it means to show up for yourself and your child. This is an episode about grief, growth, and grace—and what it looks like to reclaim your identity, your time, and your home one chickpea at a time.

How Does She Do It All: Scarlett Longstreet

In this episode of How Does She Do It All, we’re joined by Scarlett Longstreet—writer, content strategist, and single mom of three girls—who opens up about what it really takes to parent solo with purpose, grace, and a sense of humor. Scarlett shares her honest experience navigating divorce, rebuilding her life, and learning how to prioritize herself in the midst of motherhood. With warmth and wit, she reflects on the emotional weight of starting over and the strength it takes to lead a family on your own terms.

Scarlett gives us a behind-the-scenes look at how she balances raising three daughters while working full-time in a demanding creative career. She talks about the importance of building efficiencies into daily routines, the value of outsourcing when possible, and how she creates structure in a household that runs on love and logistics. She also unpacks the importance of setting boundaries, both with her kids and with herself, and why modeling joy and fulfillment is one of the greatest gifts she can give her children.

This conversation is filled with practical wisdom and deep emotional truth. Whether you're a solo mom yourself, considering the leap, or just need a dose of real-life encouragement, Scarlett’s story will remind you that single motherhood isn’t just doable—it can be expansive, grounded, and deeply beautiful.

How Does She Do It All: Adrianne Wright

In this heart-centered episode of How Does She Do It All, Olivia sits down with Adrianne Wright, a powerful storyteller, single mom, and founder of Rosie. Together, they explore the healing path of single motherhood—what it looks like to rebuild after divorce, reclaim your time, and create a life rooted in peace and intentionality. Adrianne shares candid insights from her own experience, reminding us that solo parenting isn’t just about survival—it can be a season of unexpected joy and deep personal growth.

Adrianne opens up about the quiet strength it takes to tune into your body, honor your capacity, and let go of unrealistic expectations. She talks about reshaping her daily routines to work with her life instead of against it, and how learning to ask for help has become a powerful act of self-love. From deeper connections with her children to the art of managing time with grace, Adrianne gives us permission to move through motherhood at our own pace.

This episode is a beautiful reminder that single motherhood is not a deficit—it’s a reimagining. Whether you're navigating the early days of divorce or further down the road, Adrianne’s story will inspire you to trust your rhythm, redefine what “doing it all” means, and build a life filled with love, peace, and possibility.