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.