After 700+ Conversations, Audley Stephenson Says Courage Comes Before Confidence

The Audacious Living Podcast host and author discusses personal reinvention, quiet courage and his upcoming book, Living Your Best Audacious Life Ever.

After more than 700 podcast conversations, Audley Stephenson has developed a clear message about personal growth: courage comes before confidence.

Stephenson recently joined WorldWide Entertainment TV to discuss his journey as a podcaster, author, public servant and basketball executive, as well as his upcoming book, Living Your Best Audacious Life Ever: How Unleashing Your Inner Greatness Can Change the World.

Finding audacity after the pandemic

Stephenson’s path toward “audacious living” became clearer during the COVID-19 pandemic.

At the time, he was serving as a commissioner of a basketball league and preparing for the excitement of the playoffs. When the pandemic brought the season to an abrupt halt, Stephenson said he experienced a period of depression without immediately recognizing what was happening.

“I remember literally saying, ‘Ever since I lost basketball,’” Stephenson recalled. “And the moment I said those words, I suddenly realized it’s because I don’t have basketball.”

That realization led him back to podcasting. Stephenson had first entered the podcasting space in 2008 and had already hosted several shows, including an NBA-focused podcast. Returning to the medium gave him an opportunity to create something meaningful during an uncertain period.

As he reflected on the major accomplishments and turning points in his life, Stephenson noticed a common thread.

“In every one of those instances when I achieved something great… audacity was the difference-maker,” he explained.

Audacious living means following your own path

For Stephenson, audacity is not about copying another person’s success or trying to live someone else’s life.

He described every person as having an individual path filled with challenges, obstacles, rewards and opportunities. The goal is not to constantly compare that path with someone else’s, but to understand what is meant for you.

“Your path is your own,” Stephenson said.

Living audaciously can mean stepping outside a familiar comfort zone, trying something new, entering uncertainty or taking a calculated risk. It does not necessarily require a dramatic public gesture. Sometimes, it begins with a private decision to move forward.

Three myths about audacity

During the interview, Stephenson explained that many people misunderstand what it means to be audacious.

 

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The first misconception is that audacity belongs only to the loudest person in the room or to people who perform dramatic acts, such as climbing mountains or taking extreme risks.

The second is that audacity is reserved for CEOs, elite athletes or other highly accomplished people. Stephenson countered that idea with the example of a baby learning to walk. A baby falls, gets back up and continues trying without allowing failure to define what is possible.

The third misconception is that audacity is reckless.

Stephenson said a major life change can be bold without being impulsive. Someone leaving a career, for example, can research other options, speak with people in different fields and plan the transition before making the final decision.

“An act can still be very audacious, particularly if someone has spent years in school studying” for a career they ultimately decide to leave, he explained.

Courage comes before confidence

One of Stephenson’s central beliefs is that people often wait for confidence before taking action. He believes the process works in the opposite direction.

“Courage has to happen first before you get the confidence to do anything,” Stephenson said.

He compared the process to learning how to ride a bicycle. A person does not begin with complete confidence. They take the first step, try to pedal and gradually build confidence through experience.

Stephenson also emphasized that fear and doubt are normal. The difference is that people who successfully reinvent themselves do not allow fear to control their next decision.

His years of podcasting have also become a form of personal growth. Stephenson said guests have often discussed subjects that mirrored challenges he was facing in his own life, making the podcast meaningful for him as well as his audience.

The lessons behind the new book

Stephenson’s upcoming book brings together three major sources of wisdom.

The first is the knowledge he has collected from hundreds of podcast guests. He described every guest as leaving behind a piece of insight, wisdom or experience.

The second is his own personal history, including growing up in a single-parent household, marriage and divorce, reconnecting with his father later in life, public service, basketball and podcasting.

The third is the collection of frameworks Stephenson has developed to help readers become more intentional in their actions. One of those principles is “Better Than Yesterday,” which focuses on continuous learning and improvement.

Stephenson said the book allowed him to gather lessons that would otherwise require someone to listen to hundreds of podcast episodes.

Living Your Best Audacious Life Ever is scheduled for release on December 1, 2026. Preorder information and updates are available at bestaudaciouslife.com.

Celebrating success without becoming stuck in the past

Stephenson recently passed the milestone of 700 podcast episodes, but he does not view the number as a final destination.

He said accomplishments should be celebrated, but people must continue moving forward. Reaching 700 episodes creates the opportunity to pursue 800, 900 and beyond.

The same philosophy applies to life. A past achievement can be meaningful without becoming an excuse to stop growing.

“Celebrate your wins,” Stephenson said. “Be proud of them, but don’t rest there.”

The power of small acts

Stephenson closed the interview with a story about helping a stranger find directions while he was on his way to eat a pizza.

Although he initially wanted to continue to the elevator and enjoy his lunch, he stopped to help. A woman held the elevator door for him, and the people inside began joking with him about sharing his pizza. When they exited, one of the men described Stephenson as “a really nice guy.”

For Stephenson, the moment represented something larger. A small act of kindness had created a positive experience that the people involved might later share with their families.

His final message was simple: everyone possesses inner strength and the ability to affect other people’s lives.

“Don’t let anyone tell you your light doesn’t deserve to shine,” Stephenson said. “Because it does.”

Watch and listen

Watch the full Audley Stephenson interview on WorldWide Entertainment TV and visit bestaudaciouslife.com for information about his book, podcast and social platforms.