How Does She Do It All: Olivia Howell
In this heartfelt episode of How Does She Do It All, Olivia Howell shares her journey of becoming a single mom after divorce, raising two sensitive sons, and finding unexpected peace in solo parenting. She opens up about co-parenting challenges, creating sacred routines, and building a joyful home after heartbreak. A must-listen for anyone navigating divorce recovery and single mom life.
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
What happens when you become a single mom overnight… and still have to finish the adoption process? Journalist and author Leslie Streeter joins us to share her raw, funny, deeply moving story of parenting solo after loss. From 5am wakeups and chickpea cookie dough to grief, boundaries, and outsourcing the house cleaning—this episode is a warm hug for every mom doing it on her own.
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.