Surviving the Loss of a Child

Surviving the Loss of a Child

Author: Paul Ollinger April 16, 2026 Duration: 1:04:01

“How am I ever going to be happy again?” That was the question the wife of this week’s guest asked him after the death of their one-month-old son, Fisher. Michael Cruz Kayne is a comedian, actor and a staff-writer on The Late Show with Stephen Colbert, where his work has earned him a Peabody Award, a WGA Award, and two Emmy nominations. He made his off-Broadway debut in Sorry For Your Loss, a raw, comedic, and deeply vulnerable one-man show about coping with a parent’s worst fear, the loss of a child. This is a sad but inspiring conversation. I found Michael’s attempt to make sense out of his grief and to honor Fisher’s brief life to be an uplifting act of service. You can watch the show starting March 27 on the Dropout network.

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Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 50

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