112: How to Listen (and Why)


On this episode I interview an old friend of mine, Ben Mathes, founder of the Urban Confessional, which is a free listening project. A few years ago Ben started posting up outside bus stops and on street corners with a sign that reads “Free Listening” and he would do just that: listen. Over the last couple years it’s ignited something of a movement and Urban Confessional is now in 73 countries, 2000 volunteers strong, and  has been featured in the Huffington Post, The Atlantic, Fast Company, The Big Think, Glamour Magazine, and in over 45 international publications.  His blog, HOW TO LISTEN WHEN YOU DISAGREE, has been read over 2 million times and republished in over 100 publications across the world. They are currently the subject of a PBS produced documentary called "ARE WE LISTENING", and this year, they launched the HEARD PODCAST, which features honest conversations from visionaries, leaders, and other interesting people.

On this episode we discuss how Urban Confessional started, what Ben has learned about listening over the years, how these lessons have impacted his relationships and even what it was like doing free listening at last year’s Republican and Democratic National Conventions. At the end he offers a great resource called the “Practice Partner Guide,” with some great practical tips for how to listen. It’s wonderful stuff from a wonderful human, as you’ll soon see, and the applications include, then go much beyond the college application process.



The toughest decision Ben made last year [3:18] 2:18
Ben’s process for healing [6:08]
One of the biggest challenges Ben faced [8:55]
The impact of Ben’s most difficult challenge [10:13]
Reasons why receiving generosity can sometimes be hard [13:25]
What Ben finally did that changed everything [14:43]
Why it was hard for Ben to ask for help [15:41]
What Ben has learned about how to listen [18:41]
Some of Ben’s favorite questions [21:00]
How Ben decides whether or not to go deep with someone [22:50]
The mystery of learning to walk without a destination [26:07]
Two values that come into conflict in Ben’s life [27:37]
How Ben resists wanting to fix people while listening to them [29:00]
Lessons Ben learned from his free listening project [30:29]
How these lessons have impacted Ben’s life and relationships [32:31]
Ben’s experience doing free listening at the Republican and Democratic National Conventions [35:53]
How to listen when you disagree with people [38:32]
Why Ben does what he does [40:53]