Headstone with Pete Wright

Aliza Kline has built her life around connection—the kind that happens when people gather around a table, or descend beneath the surface of the water, or find themselves saying “yes” to something unexpected. For over two decades, she’s created institutions that made those moments possible: Mayyim Hayyim, the reimagined mikveh in Boston, and OneTable, the social platform that’s helped more than a million people share Shabbat dinner. Her work has changed how Jewish ritual lives in the modern world—and how people connect to each other through it.

And now, she’s walked away.

In this conversation, Aliza joins me to explore what it means to build something that doesn’t need you anymore. What does it take to step back when your fingerprints are still visible on the work? How do you trust that the thing you’ve nurtured can keep living without you? We talk about the power of generosity, the practice of grace, and the paradox of legacy: that the things we make to last often outgrow us—and that maybe that’s the point.

From her childhood in Colorado Springs to her leadership in New York, from the living waters of the mikveh to the glow of a Friday night table, Aliza has spent her life creating spaces for people to rediscover belonging. But her real lesson is quieter: that legacy isn’t measured in names or titles, but in the courage to release control—and the faith that meaning will keep flowing, even after you’ve stepped aside.

Links & Notes

What is Headstone with Pete Wright?

A well-lived life deserves a great last line.

Headstone is a podcast about legacy—not the kind etched in marble, but the kind we carry in memory, in laughter, in the stories we tell long after someone’s gone.

Hosted by Pete Wright, Headstone uses one deceptively simple question—What do you want on your headstone?—to explore the lives behind the legacies. In each episode, guests reflect on meaning, mortality, creativity, failure, grief, and joy, finding humor and humanity in the messy middle of it all. It’s not a show about death. It’s a show about life—and the words we hope will outlast us.

Because sometimes, the story that survives you… is the best one you ever told.