Welcome back to this holiday conversation with ‘Essentialism' author Greg McKeown (see his very impressive resume below). As you set your goals and intentions for 2026, Greg’s insights will be a great way to think through WHAT REALLY MATTERS to you. To demonstrate how challenging this seemingly obvious exercise can be, I asked Greg how to help me focus my sincere but varied slate of professional ambitions. It gets a little uncomfortable, but that’s the point! And if you get one thing out of this episode, I hope it’s the 7 words Greg shares that will help you be a better spouse, parent, friend and co-worker. Thank you to my friend, the painter and 1985 high school soccer phenom, Brendan O’Connell for bringing Greg’s work to my attention. Please rate and review ⁠Reasonably Happy⁠ (Seriously, DO IT!)  Subscribe to Paul’s ⁠Substack newsletter⁠      Start your Essentialism journey ⁠here⁠    Okay, here’s Greg’s BIO: Greg McKeown has written two New York Times bestsellers: “Essentialism: The Disciplined Pursuit of Less,” which Goodreads users voted “The #1 Leadership and Success Book to Read in a Lifetime,” and “Effortless: Make It Easier to Do What Matters Most.” Together, they have been published in 37 languages. Greg is a highly sought-after public speakers globally and has spoken to over 500 companies while traveling to more than 40 countries. His clients include Apple, Google, Microsoft, and Nike. (Perhaps you’ve heard of these companies. Hmm?)  Greg hosts the cleverly named "The Greg McKeown Podcast,” which is ranked in the Top 5 of all self-improvement podcasts, and has hosted luminaries like Arthur Brooks, Matthew McConaughey, and Maria Shriver. His work has been covered in The New Yorker, The New York Times, Time, Fast Company, and Harvard Business Review…among others. 

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 ✍️

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) 📘

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.

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) 👊

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) 👊

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) 👊

Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a professional boxer and earn a degree in Physics. I spoke to Ed about his new memoir, Hard Lessons From the Hurt Business: Boxing and the Art of Life in which he shares stories about discipline, sobriety, and self-mastery. Ed and I talk bout how emotional control can outpower ego, how true masculinity is rooted in accountability, and why forgiveness is the ultimate form of strength. He also discloses that he (loves and) likes his wife! Thanks to Rob Henderson for bringing Ed to my attention. ✍️Please leave us a rating here ✍️ 🥊Learn more about Ed here 🥊 👊Get Paul’s Substack newsletter here 👊

John O’Leary’s life story has just been made into a movie called Soul On Fire, starring William H. Macy and John Corbett. When John was 9 years old, he played with fire and got burned. Like really, really burned, over 100% of his body, 87% of which were third-degree burns. Doctors gave him less than 1% chance of living and told his parents he would not survive. Yet thanks to the amazing support of his family, the community, and medical care providers, he got through it. His journey back took years, required dozens of surgeries, and cost him all of his fingers. Today, John is a world-renowned inspirational speaker who addresses large audiences around the globe. John is also the author of the best-seller On Fire!: 7 Choices to Ignite a Radically Inspired Life and In Awe: Rediscover Your Childlike Wonder Unleash Inspiration, Meaning, and Joy. He hosts the Live Inspired podcast. John and I have a lot in common. We were both one of six kids in a big, Catholic family and raised by amazing parents who were married for over 50 years and whose humility and grace inspire us to this day. We’re both husbands and dads, and both want our audiences to be radically aware of the value of their lives and the opportunity to make every day count. In this conversation, we discuss the importance of: Living in the moment Gratitude Family Courage Friends who will fight for you Finding your Talents “Saying Yes to being used for good.” ✍🏾Please leave us a rating: https://ratethispodcast.com/crazymoney. ✍🏾 👊Get Paul’s Substack newsletter: https://substack.com/@paulollinger 👊 Watch the trailer for Soul On Fire: https://www.youtube.com/watch?v=CslVGLETWps

Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50 Reflections on Money and Meaning. We cover the fun, non-obvious aspects of money and emotions, such as how comparison drives us crazy and why our bias toward action —doing something when things are going wrong — often leads to worse investment results. He offers small tips (like giving your savings account a name) that will help you save more and spend less. Daniel shares lessons from his (Mormon) mission to the Philippines, and we both reflect on how our frugal parents informed who we are today, in almost entirely (but not 100%) good ways. From the dangers of debt and overconfidence to escaping the toxic loop of “I’ll be happy when…,” we cover a lot of ground and have lots of laughs along the way. Listening to these two money-talkers with great hair will improve your life! Read Paul’s Substack: https://words.paulollinger.com/ Listen to Daniel’s podcast, Standard Deviations: https://www.standarddeviationspod.com/episodes *don’t forget the “PhD” part or he gets very mad.😁

Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the politically controversial fact that children raised in two-parent homes have better personal and professional outcomes (ON AVERAGE) than those raised in single-parent homes. Specifically, two-parent homes produce children who are more likely to graduate from high school and college, more likely to stay out of jail, to achieve stable employment, high earnings, and eventually to get married themselves, thus replicating the same advantages they had for their children. For pointing this out, Kearney was excoriated by academic colleagues who accused her of having a right-wing political agenda, which is preposterous considering that she had spent the 20 years prior to writing her book researching social policy, poverty, and inequality. Melissa is the Gilbert F. Schaefer Professor of Economics at the Unversity of NotreDame. She holds a BA in Economics from Princeton and a PhD in Economics from MIT. This is an encore episode from 2023. Follow Paul and read his work here. Learn more about Melissa Kearney here.

If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his fortune away to nonprofits tackling some of society’s most urgent challenges. In this week’s episode, Craig and I discuss the early days of Craigslist, its radical “revenue-minimization” strategy, and how its simple tools changed the classified ads game in the late ’90s. He told me how Sunday school values shaped his approach to business, why he demoted himself to customer service rep, and what he learned by hiring a CEO to run the company he built. Our conversation explores the art of giving money away strategically: from supporting veterans and military families to investing in cybersecurity and protecting democracy. We also get personal - talking favorite TV shows, the pros and cons of AI, and the big question: how much is enough? Listen now. Read Paul’s Substack here⁠: https://words.paulollinger.com/ Learn more about Craig’s philanthropic endeavors ⁠here⁠: https://craignewmarkphilanthropies.org/ Please rate, review, and share this great episode!

What happens when you mix grief, comedy, and a brutally honest take on life’s hardest moments? You get John Kenney’s new book, I See You’ve Called in Dead. In this episode, I (i.e., me–Paul–the host) sit down with John Kenney—award-winning author and longtime New Yorker contributor—for a candid and sometimes very funny conversation about writing, death, and living imperfectly, a topic we all know something about. I first learned of John 20 years ago when someone gave me a copy of his book Truth in Advertising and said, “this author is smart, wicked funny, and a little dark - you’ll love it.” I did. So I was thrilled to get the chance to talk to him about the new book and to hear a first-hand account of his journey from Ogilvy & Mather copywriter to getting published in the New Yorker and eventually becoming an award-winning novelist. One of six boys in a big Irish family, John dedicates the book to his late brother, a firefighter who died of pancreatic cancer, potentially related to his work at Ground Zero, starting the afternoon of 9/11/01. I just re-listened to this conversation, and I am grateful to John for being so open about his career, his family, and his admiration for the father who became a widower far too soon. I hope you enjoy it as much as i did. . Learn more about John: https://www.instagram.com/johnkenneywriter/?hl=enFollow Paul: https://words.paulollinger.com/

Political strategist, author, and CNN commentator Brad Todd joins Paul Ollinger for a no-BS and eye-opening conversation about what’s really happening in American politics. From growing up in East Tennessee to advising senators, governors, and big-time campaigns, Brad’s been in the trenches for decades — and he’s got the stories to prove it. Paul and Brad dig into the rise of populism, how the Republican Party has changed, and the real challenges facing Democrats in 2025. Brad gives unfiltered takes on Donald Trump’s second term, what a post-Trump GOP might look like, and why primaries and caucuses shape the country’s future. You’ll also hear what Supreme Court Justice Amy Coney Barrett was like at Rhodes College (where both Paul and Brad went to school), some high-stakes dog track bets, and why politics is still a young person’s game. It’s part insider scoop, part history lesson, part comedy — the kind of conversation that’ll make you think, laugh, and maybe even yell at your screen. If you want the truth about U.S. politics without the cable news noise, this is it.

What happens when a suburban soccer mom falls into heroin addiction, commits felonies, and ends up in prison—only to climb back out and become a four-time New York Times bestselling author? In this unforgettable episode, Paul sits down with Lara Love Hardin, author of The Many Lives of Mama Love, a mind-blowing memoir of crippling dependence, incarceration, and survival. Oprah, who picked ‘Mama Love’ for her official book club, described it as "a powerful exploration of redemption, joy, and the human capacity for change.” With unflinching honesty and unexpected humor, Lara shares her journey from PTA meetings to jailhouse shot-caller. In just a few years, she went from stealing from her neighbors to support her narcotic habit to ghostwriting best-sellers for global heroes like Bishop Desmond Tutu. Her story isn’t just about addiction or recovery—it’s about resilience, forgiveness, and how second chances can rewrite a life. If you’ve ever wondered whether transformation is truly possible, this conversation will make you believe in the messy, complicated, and inspiring fight to begin again. Learn more about the work Lara does to help women newly-released from prison get back on their feet: The Gemma Project https://www.thegemmaproject.org/ Subscribe to Paul’s Substack here: https://words.paulollinger.com/

📬 Subscribe to Paul’s Substack: https://words.paulollinger.com/ 📖 Learn more about Jonathan Rauch: https://jonathanrauch.typepad.com/ What happens when someone who grew up Jewish, gay, and atheist finds deep inspiration in the teachings of Jesus? In this fascinating conversation, Jonathan Rauch returns to the podcast to talk about his new book 'Cross-Purposes: Christianity’s Broken Bargain with Democracy'. Jonathan explains why the decline of organized religion has left a dangerous void in civic life—one now filled by hyper-partisan politics and fear-driven culture wars—and why he believes America needs a renewal of non-political Christianity rooted in courage, forgiveness, and love. We dive into his evolving relationship with faith, his hope for a less fearful, more compassionate citizenry, and the surprising ways music has shaped his worldview—including the life-changing moment he first heard Sgt. Pepper’s Lonely Hearts Club Band in third grade. Jonathan is a Yale grad, senior fellow at the Brookings Institution, award-winning author, and one of the most thoughtful public intellectuals of our time.

Andrew Heaton is the author of the new book Tribalism Is Dumb and the host of The Political Orphanage podcast. He sits down with Paul to unpack where tribalism comes from, how it is tearing us apart, and how we might fix it. With wit, warmth, and some surprisingly deep evolutionary psychology, Andrew explains how our ancient brains are wired to seek belonging—even if that means choosing teams over Truth. They cover everything from Dunbar’s number to the loneliness epidemic, from the comedy club to Capitol Hilll, and why political identity has become a poor substitute for real community. Whether you're center-left, center-right, or just tired of the noise, this conversation offers a refreshing dose of nuance, laughs, and insight into how we got here and where we could go. If you've ever felt politically homeless—or curious why shouting on Twitter feels like the new religion, this conversation is for you! Don’t miss the part where Andrew suggests that Paul change the name of his podcast to “Drinking Liberal Tears with Paul.” (It’s not going to happen, but just think of how popular it would be if we did!) Subscribe to Paul’s Substack: http://words.paulollinger.com Follow Andrew at https://mightyheaton.com/ 

This week, Paul sits down with Sarah Personette, CEO of Puck, the fast-growing news outlet the New York Times described as “Vanity Fair for the Substack era.” From her ambition to become a CEO at age seven to her senior roles at Facebook, Universal-McCann, and Twitter – which ended after Elon Musk bought the company, Sarah unpacks what it takes to lead teams through uncertainty, disruption, and reinvention. She explains Puck’s blend of high-caliber journalism with modern distribution, and how to survive the oncoming AI onslaught. Sarah speaks candidly about navigating career transitions, modeling work-life balance, leading global teams, and raising children with intention while running billion-dollar operations. Whether you're a founder, a parent, or just starting out, her mantra—“Stay calm, stay focused, stay classy”—is a playbook for thriving in today’s chaotic world. It’s a raw, funny, deeply human look at the future of media, work, and purpose-driven leadership. Also, don’t miss Paul gushing with ‘80s nostalgia about the movie About Last Night starring Demi Moore and Rob Lowe. (Don’t worry - it’s relevant) Learn more about Puck here: https://puck.news/ Subscribe to Paul’s Substack here: http://words.paulollinger.com Watch About Last Night: https://www.amazon.com/About-Last-Night-Rob-Lowe/dp/B000I8HIM2

Paul sits down with comedian and actor Mehran Khaghani and gets deep into the psyche of a man who was brought to America from Iran as a 3 year old who discovered himself after years of addiction and psychedelics only to emerge on the other side as one of the funniest comedians working today and starring in the hit Off Broadway Steven Soderbergh show "The Fears".

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 the victim mindset, narcissism, and the impact of performative vulnerability on social media. Having overcome childhood misdiagnoses that placed him in special ed classes and bullying peers, Scott went on to earn a PhD from Yale. He shares this deeply personal story of as a teachable moment to discuss mental health, cancel culture, psychological flexibility, and what truly helps us grow as humans. Thought-provoking, funny, and brutally honest—this is a must-watch for anyone navigating identity, trauma, or the modern self-help world. Scott’s other books include Transcend: The New Science of Self-Actualization and Choose Growth: A Workbook for Transcending Trauma, Fear, and Self-Doubt. Read Paul’s Substack here: http://words.PaulOllinger.com Learn more about Scott’s academic on his website and his magic and mind-reading on https://www.theamazingdrscott.show/