Reasonably Happy with Paul Ollinger

Paul Ollinger
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Jan 15, 2026 • 1h

From Apartheid to Atlanta w/ Robyn Curnow

My guest is Robyn Curnow, a native South African who spent over two decades at CNN, where she hosted CNN’s Newsroom, and anchored The International Desk with Robyn Curnow. Prior to that, she served as the network’s Africa correspondent out of Johannesburg and covered Europe out of CNN’s London Bureau. If you don’t recognize her name, I bet you’ll recognize her distinctive voice because you likely saw her interviews with some of the most prominent people of our lifetimes, including Nelson Mandela, Jimmy Carter, Bill Clinton, George W. Bush, Michelle Obama, Oprah Winfrey, and Archbishop Desmond Tutu. Robyn has covered news stories as diverse and dynamic as Africa’s HIV/AIDS epidemic, the rise of Boko Haram, the 2010 World Cup, and the murder of Jammal Khashoggi. This work earned her and her colleagues multiple Emmy nominations, the Royal Television Society Award, and the duPont-Columbia Award. On her new podcast, Searching for America—which I love—Robyn explores our society and culture through the eyes of a new-comer. Like a modern-day de Tocqueville, she offers a sincerely interested outsider’s perspective on the quirks of American life, including the Halloween Industrial complex, the obsession with high school graduation and college acceptance, turducken, and—most importantly—our collective love of Dolly Parton. She lives in Atlanta where she and I serve on a school board together. Rate and Review Reasonably Happy: https://ratethispodcast.com/paulopod Read Paul’s Substack essays here: https://words.paulollinger.com/ Listen to Searching for America here: https://open.spotify.com/show/3j83wBMdUQnOcQTfK2pg9I
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Jan 7, 2026 • 1h 12min

Rewrite Mental Illness w/Laura Delano

Laura Delano is the author of Unshrunk: A Story of Psychiatric Treatment Resistance. Laura was fourteen years old when she saw her first psychiatrist, which was not something openly discussed at the time in her wealthy hometown of Greenwich, CT. Over the next 14 years, Laura was diagnosed with bipolar disorder, depression, social anxiety disorder, eating disorder, poly-substance dependence, and borderline personality disorder. These conditions earned her prescriptions for Seroquel, Abilify, Klonopin, Ativan, Ambien, Prozac, Effexor, Celexa, Cymbalta, Wellbutrin, Lexapro, lithium, and many more. During this time, she engaged in self-harm, spent time in psychiatric hospitals, and attempted to take her own life. In 2010, Laura decided she had had enough with all the diagnoses and the drugs. Her book tells the story of how she weaned herself from this medical regimen and found a stable life free of prescriptions. You’ve gotta listen to this conversation. Laura and I talk about mental health, the pharmaceutical industry, how her behavior affected those around her, how her family dealt with their difficult sister and daughter, and how that love finally helped to see her through.Btw, the ‘80s punk band whose name I couldn’t remember around the 10-minute mark is Suicidal Tendencies. Thanks to my pal, “Nashville Ben” for recommending Laura’s book for me. Please rate and review ⁠⁠Reasonably Happy⁠⁠ (DO IT!)  Subscribe to Paul’s ⁠⁠Substack newsletter⁠⁠. Check out Laura’s website here.  NOTHING IN THIS EPISODE SHOULD BE REGARDED AS MEDICAL ADVICE. IF YOU ARE EXPERIENCING PHYSICAL OR MENTAL DISTRESS, PLEASE SEEK THE HELP OF A MEDICAL PROFESSIONAL. ALSO, DO NOT CHANGE YOUR PRESCRIPTION REGIMEN W/O CONSULTING YOUR DOCTOR.
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10 snips
Dec 18, 2025 • 1h 26min

Find your Essential Intent w/ Greg McKeown

In this conversation, Greg McKeown, bestselling author of 'Essentialism' and 'Effortless,' shares his wisdom on prioritizing what truly matters. He emphasizes the importance of choosing opportunities over obligations and offers practical strategies like the 90% rule for decision-making. Greg also discusses the impact of deep mutual understanding in relationships, revealing the seven words that can effectively de-escalate conflicts. His insights challenge listeners to evaluate their intentions and focus on meaningful pursuits in life.
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Dec 3, 2025 • 41min

High Net Worth Divorce with Laura Wasser

People magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedia—handled cases for A+listers like Angelina Jolie, Kim Kardashian, Johnny Depp, Ryan Reynolds, Dr. Dre, Kevin Costner, Maria Shriver, and Jimmy Iovine, among many others. And while “celebrity divorce attorney” might conjure up images of a rapacious shark in Prada boots squeezing every dollar out of her clients’ exes, Laura preaches the gospel of divorce with dignity. Her book, It Doesn’t Have to Be That Way: How to Divorce Without Destroying Your Family or Bankrupting Yourself is a jungle guide for ending a marriage while preserving decency, values, and a couple’s wealth. As she writes, “…the more acrimony, argument, and angst, the more money your attorney makes. We profit from your inability to resolve issues.” In other words, don’t pay your lawyer $1,000/hr to determine—as famously captured in When Harry Met Sally—who gets the “stupid, wagon wheel, Roy Rogers, garage sale coffee table.” Her book is a plea to all those going through one of the most stressful human experiences possible to summon your best self and think about who you want to be when the dust settles. Laura and I talk about the fundamental language of divorce, including spousal support, child support, no-fault divorce, community property, and also the more philosophical dimensions of the process, like the concept of “fairness” and how one defines “winning.” Sincere thanks to my former Facebook colleague, Matt Jacobson for making the connection to Laura. I appreciate, Jake! (encore presentation) Follow Laura on ⁠on Instagram⁠ and learn more about her practice ⁠here⁠.   ✍️Subscribe to Paul’s Substack ⁠here⁠ ✍️
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Nov 19, 2025 • 57min

Surviving the College Application Process w/ Jeffrey Selingo

As the father of two prep school students, I was very eager to meet this week’s guest. Jeffrey Selingo has written about college admissions for more than 25 years and is a New York Times bestselling author of four books, including Who Gets in and Why and his latest, Dream School: Finding the College That’s Right for You. Drawing on two years of research and a survey of 3,000 parents to give families permission to think more broadly about what signals a “good” college for their child, Jeff outlines the excellent choices our kids have outside of the Top 20 schools that get so much of our attention. I found his book a reassuring and therapeutic guide as our family begins the college search process. The basic message is that there are a lot of great schools for our kids out there and, with a little effort, you and I can find a place where our son or daughter will belong and thrive. And isn’t that the point? In this conversation, Jeff and I discuss the pressures surrounding elite college admissions, the evolving landscape of higher education, and the importance of finding the right fit for students. We explore the long-term financial implications of college choices, the impact of student debt, why parents are less willing to stretch financially for kids’ college expenses, and the value of college experiences beyond academics. The discussion also touches on the competitive nature of elite schools, the future of college admissions, and the weird middle ground colleges have adopted around standardized testing. A regular contributor to The Atlantic, The New York Times, and The Wall Street Journal, Jeff is also a special advisor to the president. He lives near Washington, D.C., with his own college-bound children. ✍️Please rate and review Reasonably Happy (https://ratethispodcast.com/paulopod) (Seriously, DO IT!) ✍️ 👊Get Paul’s Substack newsletter (http://words.paulollinger.com) 👊 📘Purchase Jeff’s book, Dream School (https://jeffselingo.com/books/dream-school) 📘
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Nov 12, 2025 • 44min

Paul’s Insights into NYC, Email, and Estate Planning

Hello friends. On this week’s episode, I read to you—like a daddy rocking his baby to sleep—the most recent posts from my Substack newsletter, which you can find here. (You can subscribe for free or pay a few bucks, if you want to support my work, but really I just appreicate you reading / listening and sharing.) These essays cover both life in general and some political stuff also. I put the political ones at the end, so you don’t have to involve yourself in that, if you don’t want to. But please do notice the balanced nature of my analysis, in that I am pointing out the flaws of both Left and Right, though it probably feel as if I’m being more critical of whichever team you’re on! Ain’t that weird? The Great NYC Rationalization - how living in New York requires constant self-justification How Email Will Save the World - why linear, 1990’s comms tech is better than text! The Hilarious World of Estate Planning - (it’s not really hilarious, but that’s the joke) Cancel Culture is Alive and Well - Trump, Jimmy Kimmel and free speech  Kamala’s Book is Brat AF - how the former VP’s memoir shows us how little we missed  What Bumper Stickers Tell us About America -  Please rate and review Reasonably Happy here. Get Paul’s Substack newsletter here.
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Nov 5, 2025 • 1h 5min

Confronting Mortality with Thad Reichley

Imagine being told you have a terminal illness. Would it change the way you approach each day? Two years ago, Thad Reichley went to the doctor because he had the flu. When initial attempts to address his symptoms were unsuccessful, additional procedures revealed the presence of three dozen tumors in the lining around his lungs. He was diagnosed with stage 4 metastatic melanoma. There is no known cure for the disease. A father, husband, educator, and pro-level endurance athlete, Thad’s “job” over the past 24 months has been to fight cancer and stay alive. In addition to his treatments' side effects (fever, vomiting, inflammation of the eyes, and savage bouts of colitis), Thad has learned to navigate the negative “you are not enough" voices in his head. He’s also come to change his expectations about what makes a good day. “Sometimes” he says, that while trying to carpe every diem, “just walking the dog has to be enough.” Thad and I know each other through his wife, Leigh, who was my colleague on the sales team at Facebook in LA. She’s a very funny, very committed person who, as you will hear, is no stranger to cancer. I am grateful to Thad for sharing his story and hope it inspires YOU to go to the doctor if you haven’t been in a while. As importantly, I hope that it reminds you to cherish and protect your health and loved ones for as long as you have them. Here’s how Thad sums it all up: 1. Go to the doctor 2. Listen to your wife 3. Hug your kids, and 4. Tell the people in your life you love them. Prior to his diagnosis, Thad spent two decades as an educator, both as a teacher and an administrator at well-known schools like Crossroads in Santa Monica and Mark Day School in Marin County. He earned his BA at the University of Washington, Master's degrees from both UCLA and Brown University, and his doctorate from the University of Southern California. ✍️Please rate and review Reasonably Happy (https://ratethispodcast.com/paulopod) ✍️ 👊Get Paul’s Substack newsletter (http://words.paulollinger.com) 👊
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Oct 29, 2025 • 59min

Walking Away from Fame and Money with Rachel Heck

Rachel Heck was a golf prodigy who qualified for the US Women’s Open at age 15 and made the cut. As a freshman in high school, she committed to play at Stanford University, where she went on to win both individual and team national championships and became Nike Golf’s very first NIL sponsored athlete. But when the time came to turn pro, Rachel decided that a life on the road and in the spotlight wasn’t for her. Instead, she earned and accepted her commission as an officer in the U.S. Air Force Reserve. I was very pleased to speak with Rachel, not just because she is a person of exceptional talent and character, but because she is also the daughter of my Rhodes College friends, Stacy and Robert Heck. She and I discuss her journey (so far), particular: -Struggling with perfection -The true definition of success -The importance of motherhood -How her dad “Pavlov’ed” her and her sisters into loving golf -The importance of role models, including: Condoleezza Rice (her academic advisor), Annika Sörrenstam, and Stanford Coach Anne Walker -Her favorite (and second favorite) golf course! ✍️Please rate and review Reasonably Happy (⁠https://ratethispodcast.com/paulopod⁠) ✍️ 👊Get Paul’s Substack newsletter (⁠http://words.paulollinger.com⁠) 👊
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Oct 22, 2025 • 54min

Family, Politics & The American Dream with Raj Goyle | Reasonably Happy

Raj Goyle is running for Comptroller of New York state, and he wants your support. He’s got mine because I think Raj is what America is all about. A first-generation Indian-American, Duke undergrad and Harvard Law grad, Raj was the co-founder of Bodhala, a legal spend analytics and management platform which he and team sold to Onit. As the leader of Phone Free New York, Raj led a bi-partisan effort to get phones out of the classroom across New York state. And now he wants to take his immense talent and experience to Albany for the most important position (Comptroller!) you’ve never thought about. As you’ll hear, there’s plenty that Raj and I disagree about. But he’s the kind of person we need more of in government: a smart, driven leader who wants to make government work for citizens. Among lots of other things, Raj and I discuss: -Zohran Mamdani, the NYC mayoral candidate whom Raj supports and I DO NOT -What a comptroller does -Money, happiness, and public service -What it was like for his parents–both doctors–to emigrate to the U.S. -How Jimmy Carter helped shaped his belief in ethical capitalism and an accountable government AI’s impact on the economy and what we can do about it ✍️Please rate my podcast (https://ratethispodcast.com/paulopod) ✍️ 🗳️Learn more about Raj (https://rajgoyle.com/) 🗳️ 👊Get Paul’s Substack newsletter (http://words.paulollinger.com) 👊
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4 snips
Oct 15, 2025 • 1h 11min

Stoic Street Smarts w/ Ed Latimore

Ed Latimore, a former professional boxer with a degree in Physics, shares gripping stories from his memoir, exploring themes of discipline, self-mastery, and emotional control. He discusses how his challenging upbringing shaped him and the importance of providing a loving environment for his son. Ed emphasizes the significance of sobriety in nurturing his relationships and advocates for forgiveness as a powerful means of personal freedom. With a mission to inspire youth, he reflects on the lessons learned from his life and boxing journey.

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