Episode Details

What becomes possible when you stop waiting until you’re completely ready?

Today’s guest is Chuck Mobley, an entrepreneur, pilot, author, missionary, and storyteller whose life has repeatedly taken him into situations where certainty was nowhere to be found.

Chuck describes his philosophy simply: “If you’re going to make mistakes, make them doing something going forward.”

At 22, after an oil bust left him working only limited hours in Texas, Chuck heard about an opportunity in the Cayman Islands. He had never heard of the islands before. He applied, got the job, and arrived with $100 and a three-night hotel voucher. When the money ran out, he spent several nights sleeping on the beach before receiving his first paycheck.

That willingness to step into uncertainty became a recurring theme throughout his life.

In this conversation, we explore:

• Why Chuck believes people naturally gravitate toward safety
• Why he would rather see someone make a reasonable mistake than make no decision at all
• How his “say yes first, figure it out later” philosophy developed
• The role faith has played in his life
• Why he sees faith as trusting through uncertainty rather than having all the answers
• How he went from wanting to become a Major League Baseball player to working in HVAC
• Why becoming an HVAC technician was difficult despite not being mechanically inclined
• How an opportunity in the Cayman Islands changed the direction of his life
• Arriving in the Cayman Islands with $100 and a three-night hotel voucher
• Sleeping on the beach while waiting for his first paycheck
• What failure means to Chuck
• Why he believes failure is necessary
• Why getting back up matters more than avoiding every fall
• The role of grace and second chances in his understanding of failure
• The remarkable story of how he met his wife by jumping onto a parade float
• How that leap eventually led to a 39-year marriage and four children
• What traveling through different countries has taught him about gratitude
• His experiences in Haiti, the Dominican Republic, Panama, Mexico, Tanzania, Kenya, and Uganda
• Why seeing poverty firsthand changed his appreciation for everyday things such as clean water, medicine, and shelter
• His family’s desire to give back through mission trips
• Why humor helps him navigate difficult situations
• How laughter can sometimes lighten another person’s burden
• What he learned from running out of money while traveling through Europe
• Why getting through difficult situations can build confidence
• How he thinks about purpose, destiny, and personal choice
• Why he believes God can have a plan while people still have to walk through uncertain doors
• Why excessive caution can cause people to miss opportunities
• The question he hopes people ask when they’re afraid to pursue a different life

That question is:

Why not?

For Chuck, the world is full of places we haven’t seen, people we haven’t met, and experiences we haven’t had. His philosophy isn’t that every risk will work out.

It’s that inaction is also a choice.

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📖 Chuck’s Book

Leap Before You Look, But God

Chuck explicitly identifies the book as being written by Chuck Mobley.

He says it is available in:

• Kindle
• Paperback
• Audiobook

He says listeners can find it through:

• Amazon
• Spotify
• Barnes & Noble

He also says it is supposed to be available through Audible/Amazon, although he mentions having experienced problems with that availability.

Chuck says the book was an Amazon bestseller for a period when it launched.

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