Reasonably Happy with Paul Ollinger

On this third episode of 5 Questions, I speak with Andy Borowitz, whose massively popular newsletter The Borowitz Report tops out around 200 words per post. So this intro is going to be brief!Even if you belong to Andy’s army of loyal readers, you might not know that he is also the co-creator of The Fresh Prince of Bel-Air and wrote on classic 80’s TV shows, The Facts of Life and Square Pegs, which helped to launch Sarah Jessica Parker’s career.In this fast-paced conversation, Andy and I discuss:* His career in and out of Hollywood* How to write succinctly* His grammatical pet peeve(s)* Whether AI will ever be able to write comedy* The best advice he got from Susie Essman (aka, the secret to a happy life)Subscribe to The Borowitz Report here.Subscribe to Paul Ollinger's Reasonably Happy here. See Paul tell jokes near you:• 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• July 23 - Cobbs Comedy Club, San Francisco• Aug 1 - Sticks and Stones Comedy Club, Southampton, NY• Aug 8 - Atlanta Country Club (private show)• Aug 13-16 - McCurdy’s Comedy Theatre, Sarasota, FLThat is all - have a wonderful day! Get full access to Reasonably Happy at words.paulollinger.com/subscribe

My guest today is Rosebud Baker. Rosebud is one of the sharpest and most honest voices in comedy today. She’s an Emmy-nominated and Writers Guild Award-winning writer whose credits include Saturday Night Live, Inside Amy Schumer, and That Damn Michael Che.In her new autobiography, Fully Baked: A Messy Memoir, Rosebud shares the story of being the grand-daughter of James Baker, the former Secretary of State and Secretary of the Treasury who also served as White House Chief of Staff for Presidents Reagan and George H.W. Bush.She also relates unfiltered observations on her parents’ divorce, her addiction to drugs and alcohol, her multiple miscarriages, and the death of her younger sister, Graeme.Her latest Netflix special is called The Mother Lode. She filmed half of it while eight months pregnant and the other half after giving birth. It was named one of the best comedy specials of 2025.See Rosebud’s upcoming dates and get the book here.✍️ Follow Paul Ollinger on Substack by clicking here ✍️See Paul tell jokes live near you:• 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

✍️ Follow Paul Ollinger on Substack by clicking here ✍️A.J. Jacobs is a journalist, bestselling author, self-described “human guinea pig,” and one of the most interesting people I know. He was a great choice to be my second guest on my 5 Questions series of Substack livestreams.Over the past two decades, A.J. has built a remarkable career by asking questions most of us would never think to ask—and then answering them by turning himself into the experiment.He’s read the entire Encyclopedia Britannica, lived according to the Bible as literally as possible, pursued bodily perfection, traced his family tree to millions of relatives, thanked every person involved in making his morning cup of coffee, explored the world of puzzles, and most recently spent a year trying to live according to the original meaning of the U.S. Constitution.The result has been a string of New York Times bestsellers, including The Know-It-All, The Year of Living Biblically, Drop Dead Healthy, Thanks a Thousand, The Puzzler, and The Year of Living Constitutionally. Along the way, he’s become one of America’s most entertaining guides to the intersection of happiness, curiosity, gratitude, self-improvement, and human connection.What I love about A.J.’s work is that beneath all the humor and outrageous experiments is a serious question: How should we live? And instead of lecturing, he goes out and tests ideas on himself—often with hilarious consequences.We talk about:* The United States’ 250th Birthday* Geeking out on compound anniversary words like “semiquincentennial”* What I should keep in mind while I help my kids search for colleges* Summer blockbuster moviesSubscribe to A.J.’s Substack, A.J. Jacobs Get full access to Reasonably Happy at words.paulollinger.com/subscribe

✍️ Follow Paul Ollinger on Substack by clicking here ✍️Hello friends, this week's Reasonably Happy is me reading some of my favorite posts from my Substack over the past six months. They cover the Manosphere, schadenfreude, career trajectories, and more. I understand that you don’t always have time to read everything I crank out—you’re on the move, working out, or re-arranging your sock drawer. And that’s okay. So today—as I do occasionally—I’m sending you this podcast version of me reading TO YOU. And now you don’t have any excuses to not enjoy my wonderful writing. You’re right - it’s quite generous of me, but I enjoy it. You can read all my stuff and catch some upcoming live streams here!COME SEE ME PERFORM COMEDY NEAR YOU (in Atlanta, Chattanooga, NYC, L.A., SF, Southampton, Sarasota)...* June 4: Atlanta Athletic Club (members only)* June 19-20: Comedy Catch, Chattanooga ON SALE* June 25: Couples Therapy Comedy at West Side Comedy Club, NYC* July 21: The Venice West, Los Angeles - On Sale soon* July 23: Cobbs Comedy Club, San Francisco - ON SALE* Aug 1: Sticks and Stones Comedy Club, Southampton, NY -* Aug 8: Atlanta Country Club (members only)* Aug 13-16: Headlining McCurdy’s in Sarasota, FL - ON SALE* October 15: Capital City Country Club (members only) Get full access to Reasonably Happy at words.paulollinger.com/subscribe

✍️ Follow Paul Ollinger on Substack by clicking here ✍️Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions, my bite-sized, live-streamed Substack interview show that I’ll be producing in addition to longer-form episodes of Reasonably Happy. Dave’s column was syndicated to hundreds of newspapers around the globe for several decades. He has published dozens of books on myriad topics that sold millions of copies—of books, not topics—in 22 languages. The New York Times called him “the funniest man in America.” (And when has the NYT ever been wrong?) In other words, he’s accomplished an incredible amount in the funny game, and I'm thrilled I got to talk to him. In this fast-moving 30 minute conversation, we talk about:• What he’s looking for in a nursing home.• Advice for me on shepherding my kids through the college search process (even though it doesn’t matter where they end up)• The rock band he plays in with Stephen King, Amy Tan, Roy Blount, Jr., Scott Turow, and many other• Which other authors make him laugh• What Baby Boomers could learn from Gen Z (and vice versa)Listen now and share with all your friends! Also, come see me 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 Country Club, Cashiers, NC (Talk)* 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

✍️ 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

✍️ Follow Paul Ollinger on Substack by clicking here ✍️My guest today is Roy Wood, Jr. You know him from The Daily Show and from his acclaimed stand-up specials, where he proves that smart comedy can still hit hard. A native of Birmingham, AL, Roy has that rare ability to make you laugh while also making you think—whether he’s talking about race, class, media, relationships, or the strange little hypocrisies we all live with. In addition to The Daily Show, Roy has performed on The Tonight Show, The Late Show with David Letterman, BET’s Comic View, Conan, and many other top TV programs. He is now the host of the CNN current events-comedy show, Have I Got News for You. His 2025 memoir, The Man of Many Fathers explores—among other things—Roy’s complicated relationship with his father, Roy Wood, Sr., a civil rights journalist and African American radio pioneer.Today, Roy and I talk about money, family, fatherhood, and we go deep on the craft of comedy.Speaking of comedy, see my upcoming shows below. Save the date / buy your tickets!COMEDY NEAR YOU - GET YOUR TICKETS!* May 16: QED, Astoria Queens, 9:30* May 20: Dunwoody Country Club (members only)* May 21: Atlanta Punchline - ON SALE* May 22-23: DC Comedy Loft ON SALE* June 4: Atlanta Athletic Club (members only)* June 19-20: Comedy Catch, Chattanooga ON SALE* June 25: Couples Therapy Comedy at West Side Comedy Club, NYC* July 21: The Venice West, Los Angeles - On Sale soon* July 23: Cobbs Comedy Club, San Francisco - ON SALE* Aug 1: Sticks and Stones Comedy Club, Southampton, NY -* Aug 8: Atlanta Country Club (members only)* Aug 13-16: Headlining McCurdy’s in Sarasota, FL - ON SALE* October 15: Capital City Country Club (members only) Get full access to Reasonably Happy at words.paulollinger.com/subscribe

✍️ Follow Paul Ollinger on Substack by clicking here ✍️“Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people believe that the American Dream is dead. But my guest today calls this hogwash, baloney, and complete malarkey. Joseph Moore is a historian, entrepreneur, investor, and the author of a new book called How to Get Rich In American History: 300 Years of Financial Advice that Worked (And didn’t) in which he explores how ambition, risk, and reinvention have shaped America from the very beginning. He also reveals the money myths, sacred cows, side hustles, and NAYsayers that have always been a part of our society. What if so-called timeless beliefs about money like “invest for the long run,” “compound interest builds wealth,” and “real estate always goes up” weren’t always true…and play out less often than you think they do. Joseph’s book is part history, part playbook, and part reality check. He brings lessons to life with rigor that is deeper than an oil well and a wit that is dryer than the Texas plains. And in so doing he demystifies the past in order to clarify the present for anyone thinking about money, success, and what it really means to “make it” in America.📕 Follow Joseph here. 📗 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

If you’ve ever wondered if having everything you’ve ever wanted would make you feel like a complete human being, this episode is for you. My guest today is Dr. Paul Hokemeyer, a psychotherapist who works almost exclusively with ultra-high-net-worth individuals—the kind of people most of us assume have life completely figured out. Spoiler alert: they don’t. Dr. Hokemeyer is the author of Fragile Power, a fascinating look at the emotional and psychological challenges that come with extreme wealth, fame, status, and success. In his work, he’s seen firsthand how money can insulate people from consequences, distort relationships, and quietly fuel addiction, anxiety, and isolation. In other words, he has a front-row seat to the uncomfortable truth behind the fantasy. Today, we talk about why power is more fragile than it looks, how wealth can complicate identity and purpose, and what it actually takes—whether you’re worth $10,000 or $10 billion—to build a life that feels meaningful.✍️ Subscribe to Paul’s Substack here. ✍️📈Rate Reasonably Happy here.📈👀 Learn More about Dr. Paul here. 👀 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

“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

Chris Pavone is the bestselling author of some of the smartest and most stylish thrillers of the past decade. His latest book, The Doorman is set in a glamorous Manhattan apartment building where the lives of the ultra-wealthy residents intersect with the man who quietly watches it all—the doorman. Over the course of one explosive day, secrets, class tensions, and personal betrayals collide in a fast-moving plot that doubles as sharp social satire about modern New York and the divides of race, wealth, politics, and status. This invites an inevitable and much-deserved comparison to Tom Wolfe’s Bonfire of the Vanities, though the Masters of the Universe are now fleece-vest-wearing tech and hedge-fund bros (not that there’s anything wrong with that). Full-disclosure: I loved this book. It's a page-turner! It's eminently-readable! But even more, it's an insightful look at modern society through the lens of New York City. Before becoming a novelist, Chris spent nearly two decades in book publishing, working on—or with—the editorial team for authors like John Grisham and Pat Conroy. Chris' debut novel, The Expats, became an international bestseller, won the Edgar Award and the Anthony Award for Best First Novel, and was translated into more than 30 languages. Since then he’s written a string of critically acclaimed thrillers—including The Accident, The Travelers, and The Paris Diversion—known for their globe-trotting settings, psychological depth, and characters navigating secrets, ambition, money, and power. ✍️  Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠  (DO IT!) ✍️  📚 Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE 📚🗽 Order 'The Doorman' book HERE. 🗽🚩 Follow Chris Pavone on Substack 🚩 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

This week’s podcast is a conversation with my former Atlanta neighbor, Steve Chamberlain, a former media executive whose career has intersected with some of the biggest brands and celebrities in entertainment history. I originally wanted to talk to Steve because of his experience leading the go-to-market plan of The Beatles Anthology, one of the most commercially successful recording projects of all-time. It was to be the follow-up episode to last week’s interview with Peter Doggett, author of 'You Never Give Me Your Money: The Beatles After the Break Up'.And while Steve and I discussed this at length, I found his experience as an executive vice president at Turner Broadcasting in the 1980s even more interesting. Working directly for Ted Turner, Steve’s responsibilities included everything from home video to cable syndication and World Championship Wrestling. He shares a great story about utilizing 1-900 telephone numbers to monetize wrestlers' smack talk. It’s a fun insight into the early days of a pre-Internet media “start-up.”Steve oversaw the 50th Anniversary celebrations for both Gone With the Wind and Casablanca, then—after Turner— went on to captain the release of Frank Sinatra’s Duets, which eventually led to his work with the Fab Four.Check it out here or wherever you get your podcast love.✍️ Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠ (DO IT!) ✍️📚 Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE 📚#music #movies #film #marketing #beatles #entertainment #TedTurner #wrestling #ricflair Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Money, Fame, and Misery: Meet the Beatles (w/ Peter Doggett )In the late ‘60s, The Beatles had it all: worldwide fame, critical admiration, and more money than they ever could have imagined. So why were these four young men so miserable? (And often short of cash!) My guest today is Peter Doggett—one of the great rock music writers of our time, and a man who has spent decades studying what happens when ambition, fame, and enormous piles of cash—and drugs—collide. Peter is the author of You Never Give Me Your Money, a brilliant and deeply human book about the Beatles, not only at their creative peak, but also at their breaking point, when the most successful band in history discovered that unimaginable wealth and universal adoration do not, in fact, lead to contentment and enlightenment…but do lead to lawsuits, divorce, and—sometimes—heroin addiction. Peter has written for Rolling Stone, Mojo, Q, and many others. His work has this rare quality: it makes you love the music more while feeling slightly better about your own messy life. His latest book is Surf's Up: Brian Wilson and The Beach Boys. Btw, if you like this episode, you’ll also love the new Amazon documentary about Paul McCartney called Man on the Run. Check it out.  Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠  (DO IT!)    Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE  Order Peter’s book HERE.  Get full access to Reasonably Happy at words.paulollinger.com/subscribe

My guest this week is Nir Eyal, whose two books ('Hooked’ and ‘Indistractable’) have sold over 1 million copies in over 30 languages. This week he published his latest - Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Extraordinary Results. In our chat, Nir and I discuss: Why beliefs can help us perform at our top potential (or vice versa) The difference between facts, faith, and belief How beliefs can benefit us, even if they’re not “true” The importance of cognitive flexibility And, the power of prayer, even for non-believersNir also shares a powerful story about the thing he learned by buying his mother birthday flowers from the “wrong” florist. Nir's work has been featured in the New York Times, Forbes, Harvard Business Review, Psychology Today, and many more. He attended The Stanford Graduate School of Business and Emory University. Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!) Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠  Learn more about Nir on his website. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Guess who I got to meet last week - Gina Gershon. That’s right, the incredibly beautiful and talented actress, author, singer, and long-standing disruptor of polite expectations. You know Gina from unforgettable roles in Bound, Showgirls, Face/Off, Cocktail, and a career that has zig-zagged fearlessly between Hollywood glamor, indie grit, Broadway, and music. We talked about her work and life as recounted in her new memoir, 'Alpha Pussy: How I Survived the Valley and Learned to Love My Boobs’ (a title that caught the attention of my 16 year-old son and, well, me). Gina shares stories about Prince, David Mamet, Paul Thomas Anderson, Robert Altman, Michael Mann, and Lou Reed. And she spills the beans about kissing both Tom Cruise and Jennifer Tilly (I’d go with Jen, personally). Oh, she also tells why it was so much fun to improv with Larry David on 'Curb Your Enthusiasm’. Need I say more? Okay, yes - just a little: What I took away from this interview is that artists like Gina who prioritize freedom above commerce sometimes miss out on millions of dollars and a degree of “stardom,” but they maintain their sense of self and Alpha vibe. Check it out. Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!) Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠  Buy Gina's book HERE. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Matt Kaplan is a science correspondent at the Economist and author of the new book I Told You So!: Scientists Who Were Ridiculed, Exiled, and Imprisoned for Being Right in which he shares the stories of researchers—from Darwin to Pasteur to modern Nobel Prize winners—who had to fight for their revolutionary ideas to be accepted. "But Paul…” you might say. "This sounds very interesting, but how does it fit into the conversations here on Reasonably Happy?” Good question! It’s because I like contrarians and truth-seekers. I worry about prevailing power structures or narratives that restrict innovation, progress, free markets, and personal liberty, whether those obstacles be bureaucracy, fascism, religion, or political correctness. And perhaps by pondering these historical examples, we’ll be less likely to repeat past mistakes. Over the last two decades, Matt has written about everything from paleontology and parasites to virology and viticulture. In addition to the Economist, his writing has appeared in National Geographic,  Nature, and the New York Times. He completed a thesis in Paleontology at Berkeley, and one in science journalism at Imperial College, London. In 2014 he was awarded a Knight Fellowship to study at MIT and Harvard. Born in California, he lives in England.   Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!)    Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠  Buy Matt’s book, I Told You So! here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

How do you handle it when you screw up badly? (Like really badly.) Former hedge fund trader and Wharton graduate Tom Hardin was convicted of Securities Fraud and Conspiracy to Commit Securities Fraud, which are felonies. In 2008, during the beginning of the great finanical crisis, Tom desperately needed to put some points on the board at his fund. And since everybody else in the industry seemed to be doing it, Tom allowed himself to trade equities on material, non-public information—something he knew was illegal. After being stopped by the FBI on the streets of Manhattan, Tom agreed to become an informant and wore a wire over 40 times to aid the agency in its investigation of big fish like Steve Cohen of SAC who paid a $1.8 billion fine and Rajaratnam of of Galleon Group who went to jail for 7.5 years. I spoke to Tom this week about his new book, Wired on Wall Street: The Rise and Fall of Tipper X, One of the FBI’s Most Prolific Informants. A scrappy, middle-class kid from suburban Atlanta (Go Braves!), Tom willed himself into the University of Pennsylvania’s famed Wharton School of Business, which launched him into the finance industry. He eventually earned a seat at a prestigious hedge fund and was on his way until the intense pressure of the gig led him to make a terrible decision that earned him only $46,000 but ended his career. Today, Tom works with Fortune 500 companies, financial institutions, law firms, business schools, and leadership teams, delivering keynotes and advisory engagements on behavioral ethics, culture risk, and organizational conduct. NOTE: The actor in 'Traffic’ actor whose name I was trying to remember is Benicio Del Toro, not Guillermo Del Toro. Please forgive me.Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠  (DO IT!)   Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE Pre-order Tom’s book HERE. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Ben Markovits is the author of several acclaimed novels, including his most recent release The Rest of Our Lives, which explores marriage, infidelity, empty nesting, and mortality. The book, which was short-listed for the Booker Prize, focuses on a 55-year-old law professor’s midlife crisis and transformative road trip after his children leave home. You might say it examines the sources of happiness in our lives as we age. Ben’s writing has appeared in The New York Times, The New Yorker, and The Guardian. He spoke with me from his home in England.Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠⁠ (DO IT!)   Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠  Read Ben's book ⁠NYT essay Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Erin Somers' new novel, The Ten Year Affair is a story about Millennial disillusionment (and extramarital sex). The New Yorker called it “intoxicating” and W praised the book for its “sometimes mocking examination of young middle age.” I wanted to speak with Erin because her characters reflect a sense of grown-up melancholy arising when goals like home ownership, careers, and parenthood don’t provide the fulfillment that was expected of them. So what do we do, she asks implicitly, when we find ourselves in a life designed to have meaning but does not deliver on that promise? Her characters also embody the impossible and contradictory messages society has imposed on gender roles for her generation. For men: be sensitive, inclusive, do half the housework, but still make a lot of money. For women: go conquer the corporate world while simultaneously being a present, nurturing mother and a sensual, doting wife. To me, this issue—even more than the deliciously provocative infidelity—is what has me continuing to think about the book, weeks after I finished it. Erin's writing and reportage has appeared in The New York Times Magazine, The New Yorker, The Paris Review, Esquire, GQ, The Nation, The New Republic, and elsewhere. Vogue named her first novel, Stay Up With Hugo Best, to their list of the Best Books of the Year for 2019.✍️Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠⁠ (DO IT!) ✍️https://ratethispodcast.com/paulopod📈Subscribe to ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠.📈https://words.paulollinger.com/📔Get Erin's book ⁠here⁠. 📔https://www.erinsomers.com/ Get full access to Reasonably Happy at words.paulollinger.com/subscribe

AI will have at least as big an effect on society as the invention of electricity. That’s the prediction of MIT’s Bryan Reimer. Bryan is the co-author of the new book ‘How to Make AI Useful’ in which he explores AI’s power and potential to change the world. He and I sat down this week to discuss the facts, fears, and fiction around what might be the most transformational innovation of our lifetimes. Brian offers a grounded, human-centered perspective on how AI is evolving—and why most of the extreme hype and trepidation miss the point. Rather than a doomsday takeover, he frames AI as a long-term productivity tool that works best in collaboration with humans, not instead of them. Along the way, we discuss energy demands, competition between the U.S., China, and Europe, deepfakes, “oh sh*t moments,” and how everyday people can start using tools like ChatGPT right now to improve their work and lives. Bryan is a research scientist at MIT’s Center for Transportation & Logistics and the MIT AgeLab. With over two decades of experience in human-centered technology research, he has become a leading voice in the future of mobility and making AI systems more practical, accessible, and beneficial for everyday use.  ✍️Please rate and review ⁠⁠Reasonably Happy⁠⁠ (DO IT!) ✍️📈Subscribe to Paul’s ⁠⁠Substack newsletter⁠⁠.📈📔Get Bryan’s book here. 📔 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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/paulopodRead Paul’s Substack essays here: https://words.paulollinger.com/Listen to Searching for America here: https://open.spotify.com/show/3j83wBMdUQnOcQTfK2pg9I Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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

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

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

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

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

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 doctor2. Listen to your wife3. Hug your kids, and4. 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) 👊 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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

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

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

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

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

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 producechildren who are more likely to graduate from high school and college, morelikely 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. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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

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

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

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

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.📬 Subscribe to Paul’s Substack: here.📖 Learn more about Jonathan Rauch: here. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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.comFollow Andrew at https://mightyheaton.com/ Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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.comWatch About Last Night: https://www.amazon.com/About-Last-Night-Rob-Lowe/dp/B000I8HIM2 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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

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.comLearn more about Scott’s academic on his website and his magic and mind-reading on https://www.theamazingdrscott.show/ Get full access to Reasonably Happy at words.paulollinger.com/subscribe

Zibby Owens is an author, publisher, and bookstore owner. She opens up about her writing journey, legacy, loss, and identity as the daughter of Blackstone founder Stephen A. Schwarzman. Zibby shares how grief, motherhood, October 7th, and why it’s okay–great even–to marry the tennis pro! She shares how resilience shaped her path, from launching a award-winning podcast and starting her own publishing house to writing memoirs and novels. She reflects on growing up in privilege, breaking free from societal expectations, and using her platform to speak out about antisemitism in a world that is increasingly dangerous for Jews. Zibby’s story is a masterclass in reinvention, purpose, and creative freedom.Read Paul’s Substack: https://words.paulollinger.com/ Learn more about Zibby here - https://www.zibbyowens.com/ Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 controversial case of Hunter Biden, Toobin offers sharp analysis, historical insight, and headline-worthy commentary. He discusses why Gerald Ford’s Nixon pardon was unnecessary, how the January 6th pardons expose Trump’s political strategy, and why public cynicism is fueled by elite immunity. Plus, Toobin opens up about his career, love for golf, admiration for Jim Gaffigan, and his obsession with Evel Knievel’s wardrobe. This episode delivers sharp wit, surprising revelations, and crucial context for anyone interested in politics, justice, or power.Follow Paul: https://www.instagram.com/paul_ollinger/?hl=enCheck out Jeffery's book: https://www.simonandschuster.com/books/The-Pardon/Jeffrey-Toobin/9781668084946 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 chaotic upbringing in 1950s Jewish Chicago, his complicated relationships with his parents, and the wild characters who shaped his life. He opens up about the tragic loss of his son Gabriel, how grief became poetry, and why humor and heartbreak often walk hand in hand. From poetic craft and emotional truth to the role of art in a distracted world, this is a raw, funny, and deeply moving conversation about identity, creativity, and resilience.Follow Paul on Instagram: https://www.instagram.com/paul_ollinger/?hl=enCheck out "My Childhood" in Pieces: https://edwardhirsch.com/Audio excerpted with permission of Penguin Random House Audio from MY CHILDHOOD IN PIECES by Edward Hirsch, read by the author. © Edward Hirsch ℗ 2025 Penguin Random House, LLC. All rights reserved. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 failed America's working class and what can be done to fix it. A self-described “liberal maverick,” Kahlenberg dives into his controversial role in the Supreme Court case against Harvard, arguing that socioeconomic-based admissions would promote both racial equity and fairness without alienating the working-class voters Democrats are rapidly losing. From Harvard's legacy advantages and billionaire endowments to MLK’s and RFK’s forgotten views on class over race, this episode challenges elite institutions, political orthodoxy, and the future of education in America.Check out al of Richard's books and appearances: https://www.richardkahlenberg.org/Get Paul's book: https://www.paulollinger.com/the-book Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 followed, Donald Trump harassed her on social media, calling for her arrest and accusing her of treason, Benson alleges.On this week's Reasonably Happy podcast, Benson--who is now running for governor--joins Paul Ollinger to discuss how she modernized the DMV, what it feels like to be targeted by the President of the United States, and why the Democrats' murky future. Paul pushes her to take a stand against a party that keeps falling on the sword of cultural issues with which most of America disagrees, opening the door for the very President who tried to intimidate her. Unfortunately, Benson waffles on subjects like biological males in girls' sports and the fact that most college campuses have been captured by progressive ideology. Still, it's an interesting conversation with a rising political star who, if she can stand up to her party the way she stood up to Trump, could be a solid mainstream candidate someday.Read Paul's Substack here: Http://words.paulollinger.com Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 our TikTok handles on our tombstones.Please join Paul's Substack family by following here: http://words.paulollinger.com . And, if you're so inclined, follow him on Instagram: https://www.instagram.com/paul_ollinger00:00 Introduction to the Podcast and Substack02:48 Exploring Qatar's Influence and Ethics06:02 Proposal for a Qatari Comedy Club08:57 Corporate Life Lessons from Dogs12:00 Navigating Career Changes and Authenticity18:11 The Impact of Social Media on Identity23:10 A Humorous Obituary for the Future Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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, 'Troubled', Rob lived in nine different foster homes before his 8th birthday. This takes a toll on a kid, as Rob’s memoir reveals. “By the time I was four or five, my emotions had gone underground,” he writes about the self-preservation defense that kicked in amidst the chaos. So, it probably wouldn’t surprise you that Rob was drinking before he was six years old, doing drugs at twelve, getting into fights, committing vandalism, and harboring little hope for a future beyond high school. What will surprise you is that, despite all the trauma, Rob eventually graduated from Yale and earned a PhD from University of Cambridge. Yes, that Cambridge—the one in England.Subscribe to Paul's Substack here: http://words.paulollinger.comFollow Rob Henderson on Substack here: https://substack.com/@robkhenderson/likes Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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 episode, Rob, author of Troubled: A Memoir of Foster Care, Family, and Social Class, shares his incredible journey from trauma and addiction to earning a PhD from Cambridge University. He opens up about childhood instability, military discipline, elite university culture, and his groundbreaking concept of “luxury beliefs”—status-signaling values held by the privileged that often harm the poor. This conversation is raw, eye-opening, and packed with insights about resilience, class, and what truly shapes success.Check out Rob's Substack: https://www.robkhenderson.com/Read Paul's Subtack: http://words.paulollinger.comFollow Paul on Instagram: https://www.instagram.com/paul_ollinger Get full access to Reasonably Happy at words.paulollinger.com/subscribe