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If I Don’t Laugh I’ll Cry with Molly Stillman (ep. 656)

Molly Stillman

John O’Leary welcomes Molly Stillman to the Live Inspired Podcast to inspire us to see our lives through a lens of redemption and possibility.

Molly Stillman is a podcast host, community leader and author of the forthcoming book If I Don’t Laugh I’ll Cry. She has a deep passion for inspiring others to know they were created on purpose, with a purpose, and for a purpose.

Today, Molly shares her journey of growing up the daughter of a Vietnam Army nurse, losing her mother at age 17, and squandering an unexpected quarter of- a-million-dollar inheritance in less than two years while desperately trying to find her place in the world.

Through faith, humor and finding moments of joy even in the most trying of circumstances, Molly was able to rediscover her purpose in life.

My friends, this conversation will inspire you to see your own life through a lens of redemption and possibility… while also reminding you to not be afraid to laugh at yourself every once in a while!

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  • In June 1979, Molly’s dad had a reckoning with his substance abuse after driving inebriated more than 100 miles with her 4-year-old sister and waking up in a motel room.
  • While serving as an Army nurse in the Vietnam War, Molly’s mom, Lynda Van Devanter, began partying to cope with the chaos and death around her.
    • After returning home to a divided America, Lynda struggled with depression and alcohol abuse until she finally began to heal in the early 1980s while writing her memoir Home Before Morning. Lynda became the first women’s director of the Vietnam Veterans of America’s Women’s Project and continued to face adversity in working to establish privileges military women have today. Get a copy of Lynda Van Devanter’s Home Before Morning here.
  • After two dates, Molly’s dad proposed to her mom and six weeks later were married.
  • Life is a gift. When Molly was young, her mom was diagnosed with an auto-immune disease that was triggered by Agent Orange where her body was essentially eating itself from the inside out.
  • Laughter does the heart good like medicine. – Proverbs 17:22
  • Don’t call me Shirley. In the midst of absurdity around them, Molly’s parents didn’t let that define them and still found ways to laugh and bring light to any situation, including watching the movie Airplane! together.
  • Surely You Can’t Be Serious by David Zucker, Jim Abrahams and Jerry Zucker talks about how Airplane! was formative to comedy and humor in the early 1980s and beyond.
  • As a child, Molly dreamt of being a comedian on Saturday Night Live and shares how useful learning the skills of improv are in business and in life. [My friend Travis Thomas joined the Live Inspired Podcast for ep. 20 and ep. 524 to share his journey in improv and how it brought him to become the Leadership and Team Dynamics Coach for the U.S. Men’s National Soccer Team.]
  • August 26, 2006: After receiving an unexpected inheritance for a quarter of million dollars on her 21st birthday, Molly started a downward spiral of reckless spending. In two years, not only was her inheritance gone but she was also an additional $36,0000 in consumer credit card debt that took more than four years to come out of.
  • Hope is healing. Although her personality hasn’t changed, her purpose has changed completely since discovering her relationship with God.
  • Even at her financial rock bottom, Molly tithed because it changes the heart to require obedience, trust and surrender.
  • “Pain is a much greater teacher than blessing.” Facing pain, suffering, disappointment, betrayal and embarrassment is universal in our lives, yet these challenging situations make us stronger.
  • Pre-order a copy of Molly Stillman’s book If I Don’t Laugh I’ll Cry here.

Did you enjoy today’s episode? 

You’ll love my conversation with Travis Thomas. Travis first joined the Live Inspired Podcast in March 2017 to share how improvisation shaped his life and how the three words “Live Yes And!” has helped e. He returned in December 2022 to share what a seemingly insignificant step led him to working with the U.S. Men’s National Soccer Team, and how he builds team camaraderie while also focusing on each of the players individually. Listen to Travis Thomas on Live Inspired Podcast ep. 20 and ep. 524.


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  1. Q. What is the best book you’ve ever read?
    A. The Glass Castle by Jeanette Walls.
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. Wonder.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. A portrait of my mom that my husband commissioned. My mom is holding my son Elijah who we lost during the second trimester of pregnancy.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. My mom.
  5. Q. What is the best advice you’ve ever received?
    A. From my dad: Growing old is mandatory but growing up in optional.
  6. Q. What advice would you give your 20-year-old self?
    A. Keep going.
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. I was who I said I was. I was a person of integrity, trustworthy and loyal, and I was a person who brought joy to others and stewarded the gift of joy well.