Episode 14
July 3, 2019

Asking Deep Questions

Hosted by Nadia Halim with Jan Keck Suzanne Conklin Akbari Melissa Brizuela Michael Collins Chris Piuma

Michael, reading card: “What do you think about the most when you’re by yourself?”

Chris: “Uh-oh.”

The Ask Deep Questions card deck was developed by Jan Keck as a tool for getting past small talk and into meaningful conversations. What exactly makes a question deep, and a conversation meaningful? In this episode, Jan explains to me how he came to develop the cards, and how he sees vulnerability as the key to human connection. Then, since talking about the cards isn’t nearly as interesting as using them, I get together with a group of Megaphonic hosts and friends of this podcast to tackle some of the questions themselves. We approach them with questions of our own: Is vulnerability the only key to connection, or are there other ways to connect? Can you have true vulnerability without venturing into difficult territory that risks negativity and conflict? And answering the questions on the cards does indeed spark a great, wide-ranging conversation that touches on everything from the nature of intuition, to mortality, adolescent body dysmorphia, Chris’s aversion to being remembered, and the fascinating worlds inside Michael’s head.


Jan Keck is a community addict. He is the creator of Ask Deep Questions, which started out as a deck of cards to help his friends connect on a camping trip and is now being used to facilitate meaningful conversations through sharing personal stories on every continent around the globe. Jan’s mission is to help people feel less lonely, so by creating experiences, workshops and programs he is fueling the movement for deeper human connection. Growing up as an only child, he found his soul family at summer camp, in sports clubs and even politics. But when he moved from Germany to Canada in his twenties he had to re-create his community from scratch and learned that the fastest way to make deep connections is through meaningful conversations and experiences. Jan now lives in Toronto with his wife Natalia (aka Cookie), his son Mika and cat Gato and you can often find him hanging out with his mastermind groups, attending community events, or camping up north.

The players.

Nadia Halim, your host.
Suzanne Conklin Akbari, of The Spouter-Inn.
Melissa Brizuela, returning from episode 3.
Michael Collins, of This is Your Mixtape and Dear Reader.
Chris Piuma, your producer, and host of The Spouter-Inn and The Scene Of The Scene.

Show Notes.

The Ask Deep Questions card deck.

A video introduction to the Ask Deep Questions cards, with tips on how to use them.

Support The Opposite of Lonely on Patreon and you can hear the entire conversation—and join us on a members-only Slack!