Big Questions

Big Questions celebrates its one-year anniversary with takeaways from guests over the last year.

This episode speaks to anyone who meets an unexpected and unwanted twist of fate.

For 11 years, Jordan Harbinger was the voice of The Art of Charm podcast that got up to 3 million listens a month. Then, not long ago, Jordan and his partners split and Jordan was out on his own and having a hard time sleeping.

Cal finds out how a man who worked on the FBI Crisis Negotiation Unit for 24 years incorporates what he learned on the job into day-to-day life. Cal’s biggest take-away is that people who are good at asking questions have the essential elements to negotiate well.

Ammar Kandil, Thomas Brag and Matt Dajer go on adventures that define the group’s name: Yes Theory. They say yes to tasks that make them uncomfortable, and the difficulties they encounter lead to authenticity -- which intensifies their friendship.

The star of the Netflix comedy series Unbreakable Kimmy Schmidt talks with Cal at Chicago Ideas Week about the art of being funny in an age when tastes are quickly shifting.

Some people can teach you more in an hour than you’d ordinarily learn in a decade.

For me, that person is Frank Blake – the former CEO of Home Depot. 

The astonishing part of the hour in which we conversed was that Frank schooled me about a subject I thought I knew very well – asking questions.

The author of the New York Times best-seller When joins Cal at Chicago Big Ideas week and gives him advice on the best time of the day to eat, exercise and hold meetings.

Cal talks with Rob Lawless about the changes in travel since Cal went around the world back in the 80s. Whereas Cal used magazine work to get his journey off the ground and then was passed around the world by the people he met, Rob now uses the Internet to keep his trip going.

Laura Schwab tells Cal about the circuitous journey that took her from jumping rope as a girl in Louisville to being the president of Aston Martin.

The Grammy Award-winning saxophone player gets to the essence of the way we can all get the most out of our lives through the art of being awake.

From the time he was a boy who’d contracted polio and found the saxophone to improve the strength of his lungs, David Sanborn has been making a series of connections that evolved into an extraordinary life and career.

Cal meets the best-selling author at an entrepreneurial conference in Colorado called two12 and becomes highly curious as to how Ryan can be a writer and ALSO an expert at marketing books, as well as positioning companies. Generally, when a person has one of those talents or skills, he or she is lacking in the other area.

When Cal asks the conservative talk show host about the roots of his new book, Addicted to Outrage, Glenn goes back to his childhood to explain the events that made him who he is.

Cal finds there can be life after one’s heart stops beating. Chip Conley tells him what it was like to flatline at age of 47, how he recovered and went on to sell his boutique hotel company, which put him in the surprising place where he could mentor Brian Chesky and a group of millennials who’d founded Airbnb.

Cal reconnects with the man who had the World Trade Center fall on his head and finds the lessons he learned even more powerful over time.

The two reflect upon the conversation they had shortly after Michael survived the deadliest attack on American soil. That conversation was turned into a noted Esquire Magazine story published in Michael’s own words in the January 2002 issue.