Gretchen Rubin Will Teach You to be Happy

Gretchen Rubin Will Teach You to be Happy

Author: Paul Ollinger May 26, 2026 Duration: 58:34

✍️ Follow Paul Ollinger on Substack by clicking here ✍️

“Happiness is a choice that requires effort at times.” -Aeschylus

Whenever I go back and re-listen to one of my podcast interviews, I always discover elements of the conversation I didn’t recall. Upon revisiting this 2025 conversation with best-selling author Gretchen Rubin, I of course remembered that she is a warrior for happiness and the practices that help her huge readership attain it. But listening again, I was struck by how cool Gretchen is. Not “cool” in a biker-jacket / beat poetry / clove cigarette way, but in the “I know who I am, what I’m committed to, and how I can add value to the world” way. I don’t claim to know Gretchen, but it seems logical to me that this self-awareness is a by-product of the kind of work she evangelizes. And it is work. As Aeschylus advised in the quote above, happiness is always there if we choose it, but only if—in the hard times—we are willing to get off the couch or smile through the pain. In times like these, Gretchen’s writing can help us find a path through the noise and, as she describes it, “identify ways we can take happiness from the transcendent to the concrete.” A great way to start that process is to listen (or re-listen) to this episode and take her happiness quiz here. You can also find many more applicable insights on Gretchen’s Substack, Secrets of Adulthood. Remember, happiness is growth—keep growing!

---

Come see me (Paul) tell jokes (or give a talk), in person:

* June 4 - Atlanta Athletic Club

* June 5 and 6 - Laughing Skull Lounge, Atlanta

*June 12 - Wade Hampton Golf Club, Cashiers, NC

* June 19 and 20 - The Comedy Catch, Chattanooga

* June 25 - Happy Couples Show, West Side Comedy Club, NYC

* July 21 - The Venice West, Los Angeles (on sale soon)

* July 23 - Cobbs Comedy Club, San Francisco

* Aug 1 - Sticks and Stones Comedy Club, Southampton, NY

* Aug 8 - Atlanta Country Club

* Aug 13-16 - McCurdy’s Comedy Theatre, Sarasota, FL



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: 50

Reasonably Happy with Paul Ollinger
Podcast Episodes
Jared Dillian on ‘The Awesome Portfolio’ [not-audio_url] [/not-audio_url]

Duration: 45:04
My guest today is Jared Dillian, a former Wall Street trader, DJ, and the best-selling author of Street Freak, No Worries, and his new book, The Awesome Portfolio.Let me ask you a question: Can you let your investments r…
Dave Winfield, Baseball Legend [not-audio_url] [/not-audio_url]

Duration: 50:40
If MLB first-ballot Hall-of-Famer Dave Winfield’s story tells us anything, it’s that you can’t judge a person by how things appear on the surface.What we saw from the outside: a formidable 6’6”, 220 lb athlete who had ju…
Life in the Soviet Union (w/ Vitaliy Katsenelson) [not-audio_url] [/not-audio_url]

Duration: 58:21
Vitaliy Katsenelson grew up in the Soviet Union - in Murmansk, the largest city north of the Arctic Circle. Today, he is the CEO & Chief Investment Officer of IMA (Investment Management Associates).An award-winning write…
Senator Phil Gramm Dispels Economic Myths [not-audio_url] [/not-audio_url]

Duration: 1:00:09
This week, I sit down with Phil Gramm, economist, three-term United States Senator from Texas, former chairman of the Senate Banking Committee, and co-author of 'The Triumph of Economic Freedom: Debunking the Seven Great…
‘Young Money’ with Jack Raines [not-audio_url] [/not-audio_url]

Duration: 57:39
This week, I’m talking to Jack Raines, the guy behind the mega-popular Substack Young Money and author of a great new book called Young Money: A Field Guide to Wealth and Purpose in Your Twenties.After graduating from co…
Can You Fake Happiness? w/Beth Cabrera [not-audio_url] [/not-audio_url]

Duration: 44:08
“People do not decide their futures: they decide their habits and their habits decide their future.” – F.M. AlexanderIf you want to improve, be kind to yourself. That’s the message from this week’s guest, Dr. Beth Cabrer…
Freeze the Rent! And Other Silly Policies ( w/ Paula Pant) [not-audio_url] [/not-audio_url]

Duration: 1:12:21
Last week, I received a bill from New York City for $71,1783.16. It was the balance due for my Non-primary residence surcharge, aka the pied-à-terre tax that is a premium on top of the $55k or so we pay in regular, old f…
Nobel Prize Winner on "Moral Economics" [not-audio_url] [/not-audio_url]

Duration: 49:36
This week, I sit down with Dr. Alvin Roth, Nobel Prize-winning economist, Stanford professor, and author of Moral Economics: From Prostitution to Organ Sales, What Controversial Transactions Reveal About How Markets Work…
How Empathy Is Destroying Western Civilization (with Gad Saad) [not-audio_url] [/not-audio_url]

Duration: 1:10:26
In this episode of Reasonably Happy, I sit down with Dr. Gad Saad, an evolutionary behavioral scientist, longtime professor, and author of the New York Times bestseller Suicidal Empathy: Dying to be Kind. Gad lays out wh…