In this special "Month of Jeff" episode of the Free Outside Podcast, I’m joined by the multi-talented Jeffrey James Binney—a comedian, filmmaker, ultra runner, and all-around adventurer. We dive into some deeply relatable topics like imposter syndrome, navigating failure, and finding joy in unexpected hobbies. Jeffrey shares his journey from performing on stage to running 100-mile races and thru-hiking the Pacific Crest Trail, offering insights on embracing discomfort, the power of persistence, and even how comedy shaped his resilience.

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We discuss the challenges of public success, the unpredictability of trail life, and the lessons learned from pursuing big, scary goals—whether it’s finishing an ultra marathon or creating a feature-length film. Plus, there are plenty of laughs as we explore quirky hobbies, share tales of trail mishaps, and unpack the wisdom behind knowing when to quit.

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takeaways

Imposter syndrome is common, but everyone is winging it.

Failure is a gift that teaches valuable lessons.

It's normal to feel unmotivated at times.

Stand-up comedy offers a unique sense of ownership.

The journey of trail running is filled with unexpected challenges.

Finding a coach can provide essential support and guidance.

Creativity often stems from a desire to experience everything.

Social media fame comes with its own set of challenges.

Mental health is crucial in managing public expectations.

Embrace the courage it takes to perform in front of an audience.

Sound Bites

"Nobody knows what they're doing."

"I got so bored by the end."

"You can do anything you want."

Chapters

00:00 Navigating Imposter Syndrome

11:47 The Journey of Comedy and Performance

17:15 The Highs and Lows of Stand-Up

23:14 The Transition to Ultra Running

28:59 Finding a Coach and Training for Success

33:59 Post-Trail Reflections and Future Goals

42:08 The Challenge of Writing a Book

47:15 The Journey of Solitude to Community

55:30 Navigating Expectations and Pressures

keywords: Jeffrey James Binney, imposter syndrome, motivation, failure, stand-up comedy, ultra running, creativity, social media, mental health