Kelly has a fun conversation with longtime Saturday Night Live producer Lindsay Shookus about her experiences at the legendary comedy show as well as her current work co-leading the platform and networking community “Woman Work F’ing Hard.”

“Expecting perfection is guaranteed disappointment.”

“You’re not helping the woman next to you if you’re not being honest.”

“Whenever you’re struggling, it’s so important to have a cheerleader who’s there for you.”

Kelly reminisces with Chicago-bred comedian and author Mike Bridenstine whose new book is called  “The Perfect Amount of Wrong: The Rise of Alt Comedy on Chicago’s North Side.” 

“Chicago was an improv town and everybody knew it.”

“None of it was glamorous. None of it should have worked at all.”

“During that brief period, I was forced to unlearn everything I thought I knew about comedy.” 

Kelly talks to best-selling author Morgan Housel whose book “The Psychology of Money” sold over 3 million copies. His new book, “Same as Ever: A Guide to What Never Changes,” is a fascinating look at history’s most powerful lessons.

“Asking what the biggest risks are is like asking what you expect to be surprised about.” 

“The world breaks about once every ten years, on average – always has, always will.” 

“Mind-sets are harder to repair than buildings and cash flows.” 

Kelly sits down with high-performance psychologist Michael Gervais to talk about his new book “The First Rule of Mastery: Stop Worrying About What People Think of You.”

“The sooner you fundamentally change your relationship with other people’s opinions, the sooner you become free.” 

“The idea that we can take a magic pill that makes our fears disappear is seductive but not a reality.” 

“Our interdependence is an inexorable fact of life.” 

Kelly has a timely conversation with Harvard University professor Michele Lamont to discuss her new book “Seeing Others: How Recognition Works and How it Can Heal a Divided World.”

“Identity is and has always been a basis for hateful attacks.” 

“Unlike optimism, hope is not an expression of our temperament, but a plan for the future.” 

“We cannot ignore worth any more than we can poverty or inequality.” 

Kelly spends time with Catalina Daniels and James Sherman, two entrepreneurs who met at Harvard Business School and have written a new book: “Smart Startups: What Every Entrepreneur Needs to Know.”

“Knowing you are meant to be an entrepreneur is a journey unto itself.” 

“As soon as you observe a rising tide, you’re too late.” 

“Hire for curiosity.”

Kelly talks to Jill Stoddard, the founder and director of The Center for Stress and Anxiety Management, to discuss her new book “Imposter No More: Overcome Self-Doubt and Imposterism to Cultivate a Successful Career.”

“If you didn’t care, you wouldn’t worry about being exposed as incompetent.”

“The imposter voice often grows rather than shrinks with success.”

“Our minds are master critics.”

Kelly welcomes back Suneel Gupta to the podcast to talk about his new book “Everyday Dharma: 8 Essential Practices for Finding Success and Joy in What You Do.”

“For too long, we have fixated on the future of work and ignored the future of worth.” 

“It’s easy to recognize when you’re lost in the woods. The hard part is finding your way home.” 

“As it turns out, a great work ethic requires a disciplined rest ethic.”

Kelly interviews Keegan-Michael Key and Elle Key live at the Chicago Humanities Festival to discuss their new book “The History of Sketch Comedy: A Journey Through the Art and Craft of Humor.”

“There is something about comedy that is primal.”

“Just because something is uncomfortable, doesn’t mean it’s wrong.” 

“There was always a parachute and I learned that parachute was my imagination.”

Kelly connects with Liz Tran, the founder of Reset – an executive coaching and wellness company – to talk about her new book “The Karma of Success: Spiritual Strategies to Free Your Inner Genius.”

“Our work selves and our home selves are not separate beings.” 

“Get out of your own way and allow what is already happening to happen.” 

“Play is at the center of reality.”