Reasonably Happy : Reasonably Happy Podcast

The Fragile Power of Wealth

Paul Ollinger — Thu, 30 Apr 2026 09:34:58 GMT

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.

Surviving the Loss of a Child

Paul Ollinger — Thu, 16 Apr 2026 11:17:51 GMT

“How am I ever going to be happy again?”

That was the question Michael Cruz Kayne’s wife asked him after the death of their one-month-old son, Fisher.

Michael is a comedian, actor and a staff-writer on The Late Show with Stephen Colbert, where his work has earned 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 special today on the Dropout network.

Please share this episode and the ‘Reasonably Happy’ podcast with a friend who loves thoughtful conversations.

Millionaires v. Billionaires in NYC

Paul Ollinger — Thu, 02 Apr 2026 09:53:42 GMT

Every December, I write a “Best Books I Read This Year” column for two reasons:

It provides a service to those looking for their next great book, and
I lack imagination.

But you, lucky reader, get to find out about one of my favorite books of the past several years right now because The Doorman is not just an exhilarating read, but its author is my guest on this week’s podcast.

The Doorman is a thriller set in a semi-fictitious Upper West Side apartment building called The Bohemia. It’s really The Dakota—where John Lennon was shot in 1980— and where Pavone lives with his family today.

The building provides an aquarium-like lens through which to observe the creatures swimming in its tony waters—a microcosm of New York City and how it has changed. Fifty years ago, The Bohemia housed mostly artists, celebrated academics, and diplomats. Today, Pavone writes, “as with everything else in New York, the cultural class (has been) replaced with financiers.”

Share with a book-loving friend!

The intra-1% tension is one of many insightful threads woven into a pitch-perfect dissection of money, race, status, and politics in modern New York City. The comparisons to Tom Wolfe’s Bonfire of the Vanities are inevitable and intentional.

In the podcast that you are going to listen to and love, Pavone told me he set out to write a modern version of Bonfire, a New York crime novel that is “about racism, but also about class…which is often what we’re talking about when we talk about race.”

He brings it to life through his characters. There’s Chicky Diaz, the eponymous doorman who carries crushing medical debt while serving the building’s elite. Among them are the ethereal Emily Longworth and her husband, Whit, a sketchy billionaire with more money than taste.

But the most interesting conflict isn’t between rich and poor, it’s within the rich. Julian Sonnenberg, the Longworth’s art dealer, has cultural capital but fading finances. While he and Whit are neighbors, they definitely are not equals. And each of them is acutely aware of this.

Julian sums it up, “The corrosive thing about New York is that there’s always someone with more — more money, more fame, more power, more respect.”

Nobody needs to feel sorry for Julian, who is part of what Pavone calls the “normal rich,” like lawyers who take nice vacations and belong to a country club or two. They don’t worry about having cash for a taxi, but in NYC they do worry. About the billionaires above them. About being fired for saying something insensitive at work. About the $70,000 tuition at private schools, where teachers wear “Tax the Rich” t-shirts on parents’ day. About where their kids will go to college. Sure, Chicky’s girls got into Ivy League schools, but will Julian’s white children be given the same consideration?

Pavone asks many questions, but answers few. For all his diagnosing the ills of virtue-signaling, inequality, and racism, his politics remain opaque, much to the reader’s benefit. If we were to ascribe motives to the author, we would stop observing the characters and start judging them.

Instead, he just presents us with the aquarium and lets us watch the fish, to notice which ones are circling. And which ones are getting eaten.

THE END (but see comedy dates below ↓↓↓)

New Comedy Dates: Added San Francisco and L.A.!

May 3: Charlotte - Duckworth’s - ON SALE
May 7: Private School Comedy, West Side Comedy Club, NYC
May 20: Dunwoody Country Club (members and guests only)
May 21: Atlanta Punchline - ON SALE
May 22-23: DC Comedy Loft (tickets available soon)
June 4: Atlanta Athletic Club (members and guests 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
July 23: Cobbs Comedy Club, San Francisco ON SALE
August 8: Atlanta Country Club (members and guests only)

The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain

Paul Ollinger — Thu, 26 Mar 2026 04:04:49 GMT

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.

Bye!

Money, Fame, and Misery: Meet the Beatles

Paul Ollinger — Thu, 19 Mar 2026 10:09:37 GMT

Greetings from New York City where it’s still too damn cold. But around the corner waits a 2-week spring break, which will hopefully provide the bridge to an actual spring. But who knows.

I’m writing today to share that I have moved my podcast to Substack. It will still be available on Spotify, Apple Podcasts, and a dozen smaller podcast apps, but will be hosted on the Substack platform, so also available on the Substack app.

The first episode is a new interview with Peter Doggett, one of the great writers of the rock era 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: The Beatles After the Breakup, a deeply human book about the legendary band, not only at their creative peak, but also at their breaking point. It chronicles the time 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 the rare quality of making you love the music even 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.

Know a Beatles super-fan? Send this interview to them!

Believe and You Will See! (w/ Nir Eyal )

Paul Ollinger — Thu, 12 Mar 2026 10:00:00 GMT

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-believers

Nir 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.

Gina Gershon on Fame, Desire, and Boobs

Paul Ollinger — Thu, 05 Mar 2026 11:00:00 GMT

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!)
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Buy Gina's book HERE.

The Courage to Be Right w/ Matt Kaplan

Paul Ollinger — Thu, 26 Feb 2026 11:00:00 GMT

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.

Insider Trading w/Tom Hardin

Paul Ollinger — Thu, 19 Feb 2026 11:00:00 GMT

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!)

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Pre-order Tom’s book HERE.

Surviving Middle Age w/ Ben Markovits

Paul Ollinger — Thu, 12 Feb 2026 18:38:00 GMT

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!)

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Read Ben's book ⁠NYT essay

Marriage, Infidelity, and Millennial Disillusionment with Erin Somers

Paul Ollinger — Thu, 05 Feb 2026 11:00:00 GMT

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/

A.I. Facts, Fears and Fiction (w/ Bryan Reimer)

Paul Ollinger — Wed, 28 Jan 2026 12:00:00 GMT

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!) ✍️

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📔Get Bryan’s book here. 📔

From Apartheid to Atlanta w/ Robyn Curnow

Paul Ollinger — Thu, 15 Jan 2026 19:15:00 GMT

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

Rewrite Mental Illness w/Laura Delano

Paul Ollinger — Wed, 07 Jan 2026 13:48:00 GMT

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.

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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.

Find your Essential Intent w/ Greg McKeown

Paul Ollinger — Thu, 18 Dec 2025 11:00:00 GMT

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!)

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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.

High Net Worth Divorce with Laura Wasser

Paul Ollinger — Wed, 03 Dec 2025 13:03:00 GMT

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 ✍️

Surviving the College Application Process w/ Jeffrey Selingo

Paul Ollinger — Wed, 19 Nov 2025 12:00:00 GMT

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!) ✍️

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📘Purchase Jeff’s book, Dream School (https://jeffselingo.com/books/dream-school) 📘

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

Paul Ollinger — Wed, 12 Nov 2025 12:00:00 GMT

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 -

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Confronting Mortality with Thad Reichley

Paul Ollinger — Wed, 05 Nov 2025 11:00:00 GMT

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) 👊

Walking Away from Fame and Money with Rachel Heck

Paul Ollinger — Wed, 29 Oct 2025 13:45:00 GMT

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) 👊