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
How to Live a Stress-free Financial Life with Jared Dillian [not-audio_url] [/not-audio_url]

Duration: 1:00:00
Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on the little things like that daily Starbucks latte. Jared Dillian thinks th…
Judd Apatow on Money, Fame, and Adam Sandler (Encore) [not-audio_url] [/not-audio_url]

Duration: 48:26
Judd Apatow is one of the most important figures in comedy and film today. But he just doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, dir…
Author Gary Sernovitz [not-audio_url] [/not-audio_url]

Duration: 59:08
Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’s Chief Investment Officer who is suffering a mid-life crisis. If you poss…
How to Get Un-stuck with Merrick Furst, Ph.D. [not-audio_url] [/not-audio_url]

Duration: 1:06:24
Do you ever feel stuck in life? As if you are in the wrong place or you’re in the right place but doing the wrong thing? What do you do when you find yourself at a crossroad? Today, I speak to innovation expert Merrick F…
Paul Reads His Thanksgiving Essays [not-audio_url] [/not-audio_url]

Duration: 35:41
In this special “over the river and through the woods” episode, Paul reads four of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts includ…
Ed Begley Jr. on Finding Serenity in Hollywood [not-audio_url] [/not-audio_url]

Duration: 38:45
✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️🎤 See Paul’s upcoming comedy dates here and random thoughts on Instagram here. 🎤Ed Begley Jr. has been acting professionally since 1967 when he appear…
Lessons from an '80s Guitar god with Rik Emmett of Triumph [not-audio_url] [/not-audio_url]

Duration: 1:05:15
Rik Emmett is a vocalist, guitarist and former member of the rock band Triumph, which earned 18 gold and nine platinum records in Canada and the United States in the late 1970s and early’80s. Triumph was known for its BI…
The NHL, Brain Injury, and Psilocybin with Daniel Carcillo [not-audio_url] [/not-audio_url]

Duration: 50:17
When Daniel Carcillo played in the NHL, he was known as an enforcer so tough and volatile that he earned the nickname “Car Bomb.” In his 12 seasons in the NHL, Daniel was a member of two Stanley Cup-winning teams (2013 a…

«1...678910