Working backwards to tackle big projects

Amy and Chris outline using goals-first planning to remodel, travel, and accomplish large family ambitions.

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Episode notes

Amy Winther is the Head of Product Design for Core Products at Square and the writer behind Motherboard, a Substack sharing honest stories about senior women in big tech. Chris Winther is a former financial planner turned stay-at-home dad and the primary parent for their three kids.

They’ve built a family setup that flips the traditional script. Amy’s the full-time working parent and Chris runs the home. And what’s wild is how fast it came together. One brutal childcare moment, their third nanny situation falling apart, and they made the call in basically an hour. We discussed:

Childcare chaos that forced a fast decision: The nanny and scheduling breaking point that made them change their whole setup in basically an hour.
Flipping the traditional script: Why Amy stayed in her career and Chris became the primary parent, and what surprised them about how it felt in real life.
Money, power, and partnership: How “what’s mine is yours” removed tension early, and how they split ownership across work and home without resentment.
Being the only dad in kid spaces: The awkwardness at playgrounds and playdates, the “creepy guy” fear, and how Chris found his footing and community.
Schools and doctors calling mom first: The practical playbook for getting institutions to recognize the primary parent, even when defaults are outdated.
Their annual family meeting system: The repeatable way they plan goals, calendars, health, and money so life doesn’t just “happen” to them.

Where to find Amy Winther