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.

✍️ Subscribe to Paul’s Substack here. ✍️

📈Rate Reasonably Happy here.📈

👀 Watch Sorry for Your Loss here. 👀



Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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: 100

Reasonably Happy with Paul Ollinger
Podcast Episodes
How Victimhood and Narcissism Hold Us Back (w/ Scott Barry Kaufman) [not-audio_url] [/not-audio_url]

Duration: 50:05
Scott Barry Kaufman is a cognitive scientist and best-selling author of the book Rise Above: Overcome a Victim Mindset, Empower Yourself, and Realize Your Full Potential. Scott’s writing dives deep into the psychology of…
Jeffery Toobin on Presidential Power | Reasonably Happy Podcast [not-audio_url] [/not-audio_url]

Duration: 58:30
CNN legal analyst and bestselling author Jeffrey Toobin breaks down the hidden power of presidential pardons — and how they reveal the true character of American presidents. From Trump’s transactional pardons to the cont…
A Poet’s Wild Past w/ Edward Hirsch [not-audio_url] [/not-audio_url]

Duration: 50:46
Acclaimed poet and Guggenheim Foundation president Edward Hirsch joins us in an unforgettable episode to discuss his powerful memoir My Childhood in Pieces: A Stand-Up Comedy and a Skokie Elegy. Hirsch reflects on his ch…
Has Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger [not-audio_url] [/not-audio_url]

Duration: 53:12
Has affirmative action failed in America??In this eye-opening conversation, Richard Kahlenberg—author of Class Matters and a longtime education and housing policy scholar—explains why race-based affirmative action has fa…
Facing Down Trump with Jocelyn Benson [not-audio_url] [/not-audio_url]

Duration: 45:15
In December 2020, Michigan Secretary of State Jocelyn Benson was decorating the family Christmas tree with her 5-year-old son when she heard a crowd outside her home chanting "Stop the Steal!" In the days and weeks that…
Paul Wants $$ From Qatar (and other hilarious Substack posts) [not-audio_url] [/not-audio_url]

Duration: 26:55
This week, Paul reads his three most recent Substack posts, including: A very funny take on Qatar's bribery of pretty much every institution in America, How his dog's feel about castration, and Why many of us will have o…
From Chaos to Cambridge [not-audio_url] [/not-audio_url]

Duration: 55:31
Rob Henderson’s dad walked out when Rob was an infant. Not long after, Rob’s drug-addicted mother placed him into the foster care system and a near-constant cycle of neglect and displacement. According to his 2024 book,…
From Chaos to Cambridge - Rob Henderson [not-audio_url] [/not-audio_url]

Duration: 55:31
He was drinking by age five, shuffled through ten foster homes, and emotionally shut down by the time most kids are starting kindergarten — yet Rob Henderson clawed his way from chaos to Cambridge. In this powerful episo…