After more than fifteen years working to the top of luxury fashion, culminating in her role as COO of Brandon Maxwell, Lauren Phelps walked away. She had just lost her mother to brain cancer and was pregnant with her first son, and she realized something: the memories she carried of her mom weren’t the milestones or big moments, trips and celebrations. They were the in-betweens. The way her mother brushed hair away from her face during a bedtime story. The songs. The painting together on the back porch. She didn’t want to miss those moments with her own children.

Today, Lauren is a fine artist working out of her studio at the historic National Arts Club in Gramercy Park, where her oils, charcoals, and pastels are devoted almost entirely to the bond between parent and child. She is currently illustrating a book with bestselling author Michael Sampson (out soon), with her own debut as author-illustrator launching in 2027.

In this episode, Lauren and I get into the big little moments, and we bond, hard, over what it’s like to raise deep-feeling kids who show those feelings in wildly different ways. Our older ones tend to process through complication and quiet; our younger ones leave nothing unsaid. We close the conversation with Lauren in the middle of a real one: her 8-year-old is scheduled to perform an almost unbelievably complex musical piece in front of his entire school the next day, and he’s wavering. We talk through how to hold space for a child who is caught between wanting something and being terrified of it.

(An update from Lauren the morning after we recorded: he performed. He was incredible.)

This one is two moms pulling back the curtain on what it actually feels like to parent big-feeling children and on holding each other up while we do it. I hope it helps you and you connect with it the way we did with each other.

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