Growing Older with Gusto

The Power Of Humor: Navigating Life's Ups And Downs With Greg Schwem

Growing Older with Gusto

Show Notes

Ever wondered how to navigate life's challenges with a smile? Join Gail Zugerman in a hilarious and insightful conversation with Greg Schwem, a well-respected corporate comedian and cruise ship entertainer who has turned life's gut punches into punchlines. Discover how Greg's superpower – humor – helped him navigate a gray divorce and a cancer diagnosis, all while keeping his audience laughing. Plus, get ready for some witty insights on online dating, the importance of human connection, and the power of laughter in the face of adversity.

Greg has recently written a book about his personal life called, “Turning Gut Punches Into Punchlines“.

He is on SIRIUS Radio and Comedy Central and has shared the stage with Jay Leno, Celine Dion, and Keith Urban!

—

Watch the episode here

Listen to the podcast here

The Power Of Humor: Navigating Life's Ups And Downs With Greg Schwem

How To Use Humor To Get Through Life's Curve Balls

Welcome to the show. This is a show that provides a platform for older people who are growing older in a positive and productive way to come on stage and dispense their wisdom. You can find out more about our show by going to www.GrowingOlderWithGusto.com. We have a very special guest for the holidays from the start of the new year who happens to be a comedian from Chicago. He is navigating the ups and downs of life by utilizing his superpower as a comedian and using his great sense of humor. His name is Greg Schwem. He spends much of his professional time on stage and onboard cruise ships.

The Chicago Tribune has proclaimed him as “The King of the Hill” in the growing world of corporate comedy. He's been on Sirius Radio and Comedy Central and has shared the stage with the likes of Celine Dion, Jay Leno, and Keith Urban. We're going to talk to Greg about how changes later in life don't necessarily have to be as scary as you might think if you find the humor in difficult, challenging, and unfamiliar situations. Greg has also written a very funny book based on his own personal life called Turning Gut Punches into Punch Lines. There's a lot to talk about with Greg so let's get going.

Welcome to the show, Greg.

Thank you for having me. Superpowers, I love that. I don't think I've ever been introduced as having superpowers. That's a lot of pressure.

From Journalist To Comedian: Greg Schwem's Unlikely Path To Success

Why don't we begin by having you tell our audience a bit about how you got started as a corporate speaker which the Huffington Post has called you “Your boss's favorite comedian”?

It's weird. I quit my job in journalism. I was a newspaper and a TV reporter in West Palm Beach, Florida. I did that for the first five years out of college. I was always a comedian though. I always did it as a hobby. I started doing it in high school. I finally decided after five years in journalism, which doesn't sound like a lot but it is a lot. It takes a toll on you, particularly with the kind of stories that I was covering which were certainly not funny. They were very depressing. I told a lot of morbid stories. I would do that during the day and then I would go to comedy clubs at night and make people laugh. I eventually decided I liked doing that better so I moved back to Chicago.

I became a club comedian, the guy who goes around to clubs around the country and makes people laugh. Little by little, I started getting approached because of the type of material that I was doing in my standup act. I was doing material about computers, business, meetings, and that kind of stuff. I would have people come up to me afterward and invite me down to their Christmas party, their golf outing, or little stuff like that. That snowballed. The more shows that I did for business groups, the more I got noticed by people who booked those kinds of events on a much larger scale. I was getting approached by corporate speakers bureaus, corporate booking agents, and meeting planners.

It is a word of mouth marketing, so to speak.

More from Growing Older with Gusto

Oct 16, 2026

Receiving a home after losing a loved one brings a heavy emotional toll alongside complex real estate decisions. Knowing how to protect your family's interests and avoid predatory cash buyers is crucial when navigating inherited property. In this episode, host Gail Zugerman sits down with Rhett Fruitman, co-founder and CEO of Inherited Property Match, to explore the critical steps heirs must take during a difficult transition. Discover how his nationwide service vets probate specialists, aligns co-heirs, and helps families manage timelines, carry costs, and tax considerations completely free of charge.

Oct 5, 2026

Navigating your retirement years with complete financial peace of mind starts with a clear, personalized Retirement Planning Process. Host Gail Zugerman sits down with wealth manager John Link to discuss how everyday retirees can build confidence without chasing unpredictable market returns. He reveals why conventional asset division between adult children can quietly trigger massive tax imbalances, introducing the crucial concept of estate equalization. You will discover practical ways to coordinate Social Security timing, manage unexpected healthcare costs before Medicare kicks in, and eliminate the paralyzing fear of running out of money. John Link also outlines his structured framework for enjoying hard-earned resources early through dedicated lifestyle accounts instead of leaving wealth behind by accident.

Sep 25, 2026

Growing older comes with endless physical and lifestyle changes, but navigating aging with humor can make every step of the journey far more enjoyable. Self-described sit-down, stand-up humorist Diane Dean-Epps joins this episode to discuss how laughter serves as an essential coping mechanism through life's unexpected twists and turns. As the author of Bangs 'N' Botox: My Aging Journey Into, Through, and Beyond Denial, Fillers & Human Preservatives and host of the BANGS ‘N’ BOTOX™: Women Who Wear Aging Well show, Diane shares her personal lightbulb moments—from doctor visits to total hip replacements. In this episode, explore how changing your perspective, staying active, and embracing life’s absurdities can help you grow older with gusto.

Aug 8, 2026

Host Gail Zugerman welcomes return guest Sky Bergman, an award winning film Documentarian, to discuss her latest project about finding humor as we grow older. Bergman shares the backstory behind "The Jollytologist", a documentary centered on Allen Klein and the healing power of laughter. She explains how simple attitude shifts and everyday curiosity pull anyone out of a rut. Bergman also talks about her path from Professor Emeritus of Photography and Video at Cal Poly, San Luis Obispo to full-time filmmaker. Listeners gain tactical insights on staying connected, pursuing new passions, and finding joy in life's smallest moments. She also previews her other recent projects, including "Lives Well Lived" and "Mochi".

Aug 1, 2026

Navigating life after work requires more than financial planning when your sense of self vanishes overnight. Retirement mindset mentor George Jerjian joins host Gail Zugerman to explain how individuals can successfully transition into their next stage of life using DARE Method Retirement strategies. By focusing on four key phases—discover, assimilate, rewire, and expand—you can shed your old professional identity and reconnect with your authentic self. George shares practical insights on taking a purposeful gap year and reprogramming your mindset for active growth. You'll learn why traditional retirement is an artificial concept and how staying engaged protects your long-term vitality. Discover how to create a meaningful second act and avoid falling into post-career stagnation.

See all episodes →