Surviving the College Application Process w/ Jeffrey Selingo

Surviving the College Application Process w/ Jeffrey Selingo

Author: Paul Ollinger November 19, 2025 Duration: 55:16
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

Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 100

Reasonably Happy with Paul Ollinger
Podcast Episodes
Fire Up Your Marriage with Carolyn Sharp | Reasonably Happy [not-audio_url] [/not-audio_url]

Duration: 54:17
"Love isn't enough." So says marriage expert Carolyn Sharp in her new book 'Fired Up: Four Secrets to Reigniting Intimacy and Joy in Your Relationship.' Paul talked with Carolyn (a college friend) this week and dove deep…
Comedian Matt Ruby | Reasonably Happy [not-audio_url] [/not-audio_url]

Duration: 56:53
Join Paul as he sits with the very funny Matt Ruby and discuss performing on psychedelic mushrooms, being raised by a bohemian mom who ran around New York City with Alan Ginsberg and more!Links to all things Matt Ruby in…
Nathan Macintosh | Reasonably Happy [not-audio_url] [/not-audio_url]

Duration: 57:09
Join hilarious comedian and hater of all things technology Nathan Macintosh as he sits with host Paul Ollinger and discusses his love hate for tech, the overabundance of screens in socoiety and the fear of what AI will d…
Paul Shaffer | Reasonably Happy [not-audio_url] [/not-audio_url]

Duration: 1:02:44
Join legendary musician Paul Shaffer, famed as David Letterman’s long-time musical director, as he shares his extraordinary career journey—from his childhood in Thunder Bay to iconic roles on Saturday Night Live and The…
Deepak Chopra & Dr. John Kaag | Reasonably Happy [not-audio_url] [/not-audio_url]

Duration: 52:46
Paul sits down to talk happiness with Deepak Chopra who is a world-renowned pioneer in integrative medicine and personal transformation alongside award winning author, professor, writer and speaker Dr, John Kaag.Visit Re…
Rickey Smiley: Living with Loss | Reasonably Happy with Paul OIlinger [not-audio_url] [/not-audio_url]

Duration: 48:59
Paul sits down with comedian and syndicated radio legend Rickey Smiley and talk about happiness in the face of grief after losing a son to opioid addiction, surviving being shot at point blank range and continuing a life…
Is music meaningless? | Reasonably Happy with Paul Ollinger [not-audio_url] [/not-audio_url]

Duration: 56:18
Paul is joined by SNL music director Eli Brueggemann to discuss everything from what landing a gig like Saturday Night Live does for a musician to how quickly a masters level university degree can become outdated because…
I sleep with a blankie | Reasonably Happy with Paul Ollinger [not-audio_url] [/not-audio_url]

Duration: 56:17
Paul sits down with lawyer turned comedian Liz Glazer to discuss how a successful lawyer and law professor can find happiness by saying goodbye to a tenured career by pursuing a life in the arts.Follow Reasonably Happy h…