Persistence, Positivity & Collaboration: Sarah Ray on Joy-Based Delegation and Building Career Momentum With Two Under Five

When I sat down with my second Look Both Ways guest, Sarah Ray, it reminded me why I love talking with her so much. She takes what could be one of the most exhausting seasons of life and reframes it with clarity and optimism.

To her, parenting is its own version of progressive overload—the gradual increase in stress that ultimately builds strength. In other words, the hard stuff is what makes us stronger.

We talk about her philosophy of joy-based delegation, raising grounded and well-rounded barn kids who can tack up a horse before they can recite the alphabet, and the sanity-saving reminder that every phase of parenting is just a season.

Sarah is hungry, driven, and endlessly curious—qualities that have fueled her career in health tech. But her story also includes postpartum anxiety, imposter syndrome, and the too-familiar blurring of work and life (including a conference call with her six-day-old baby on her chest). With baby number two, she’s finding her stride.

And yes, you’ll also hear mentions of Taylor Swift, Jimmy Buffett, and the classic business book The E-Myth.

Here is Sarah’s story.