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Parenthood didn’t just change our guest’s calendar; it rewired her relationship with work. Kaleana Quibell spent years inside Bay Area benefits, rolling out wellness, mental health, and family programs for marquee tech companies. Then two kids, an eight-minute delivery room sprint, and a parade of sick days revealed what the slide decks missed: policies don’t parent; people do. She chose a different path—part-time caregiving, part-time consulting, and a new platform, Both And, that maps real options for working families.

We dig into the practical moves that make flexibility real. Kaleana explains why to set up an LLC before you “need” it, why a simple website and scope template save hours, and how to quote your first “pick your brain” call without flinching. We unpack health insurance for independents, state leave programs, and the growing set of platforms bundling coverage with invoicing. If benefits have kept you tethered to a job that no longer fits, this is your permission slip—and your playbook—to build a safety net outside the org chart.

Care gets reimagined, too. Instead of outsourcing the moments that matter, Kaleana shows how to offload everything else: a mother’s helper for two hours, a retired neighbor for errands, targeted help for laundry or car seats. That patchwork approach turns invisible labor visible, lowers stress, and catches the inevitable surprises—school closures, coughs, and last‑minute travel—without blowing up your week. We also confront culture head-on: how “above and beyond” rewards availability over outcomes, how moms are judged on extras, and why consulting can flip the power dynamic to pay for results.

By the end, you’ll have a clearer map for stay, shift, or step away: negotiating part-time or IC roles, keeping a toe in your craft, and measuring success by time, health, and presence—not just salary. Ready to design a career that fits your family and your ambition? Listen, share with a friend who needs options, and subscribe for more real‑world playbooks. Then tell us: what’s the first lever you’ll pull to reclaim your time?

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