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 sisterโ€”and co-founder of Fresh Startsโ€”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 soloโ€”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 doesnโ€™t sugarcoat the hard partsโ€”parenting two deeply feeling, wildly different boys in todayโ€™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. Itโ€™s also a gentle reminder that the key to โ€œdoing it allโ€ might just be learning to do it differentlyโ€”with intention, with support, and with the fierce belief that your sacred space is wherever you decide to rebuild it.

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How Does She Do It All: Lisa Easton

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How Does She Do It All: Leslie Gray Streeter