7 Documentaries Every Freelancer and Entrepreneur Should Watch for Inspiration

The road to success is often challenging. Whether you’re building a business, pivoting into a new career, or navigating the complexities of working for yourself, perseverance, discipline, and self-belief are required. But how do you stay motivated when the going gets tough? Sometimes, all it takes is seeing how others have overcome their own obstacles to reignite that spark within you.

We’ve curated a list of seven documentaries that we believe have the power to change your perspective, inspire resilience, and motivate you to take on any challenge. From mastering a craft to pushing beyond limits, these films showcase the incredible feats that are possible when you dare to dream and pursue your passion relentlessly.

1. Jiro Dreams of Sushi

This documentary chronicles the life of Jiro Ono, the most famous sushi chef in Tokyo, who, even at the age of 85, continues to strive for perfection in his craft. Jiro is the only chef to hold a three Michelin star rating and has been declared a national treasure in Japan. Yet, he doesn’t believe he has reached the peak of his career. His relentless pursuit of excellence proves that true success comes from immersing yourself in your work and continuously improving.

For freelancers and entrepreneurs, Jiro's story serves as a powerful reminder that mastering your craft and falling in love with what you do is key to achieving greatness. No matter where you are in your career, there is always room to grow and refine your skills.

2. The Dawn Wall

The Dawn Wall is a breathtaking documentary that follows rock climbers Tommy Caldwell and Kevin Jorgeson as they attempt to scale the unclimbable Dawn Wall of El Capitan in Yosemite National Park. This monumental feat took six years of meticulous planning and drew global attention as they embarked on the impossible.

For anyone questioning their path, this documentary helps you reconnect with your why. It’s about pushing yourself beyond perceived limits and discovering that you're capable of much more than you ever imagined. In the face of seemingly insurmountable odds, Caldwell and Jorgeson remind us that with enough determination, anything is possible.

3. Money Explained

Money management is a critical skill for freelancers, entrepreneurs, and remote workers, and Money Explained offers a crash course on the complexities of finance. This documentary series delves into our relationship with money, exploring topics like loans, debt, and financial planning. It provides valuable insights into how we can better manage our finances and make informed decisions.

This fact-based documentary is backed by extensive research, making it an essential watch for anyone looking to take control of their financial future. Understanding money is key to thriving in the gig economy, and this series will show you how you can build a solid foundation for your financial health.

4. Man on Wire

Man on Wire is the awe-inspiring story of Philippe Petit, who in 1974 walked a high wire between the twin towers of New York's World Trade Center. It was a daring act that defied logic, and Petit’s unwavering dedication to his dream is nothing short of inspiring.

This documentary is a masterclass in audacity and passion. Petit's story is a powerful reminder that sometimes, the most incredible achievements come from pursuing what others deem impossible. For those in a rut or facing a daunting challenge, Man on Wire provides that much-needed push to keep going.

5. The Defiant Ones

The Defiant Ones is a riveting music documentary that chronicles the rise of Jimmy Lovine and Dr. Dre, two industry legends who forged an unlikely partnership and revolutionised the music world. From humble beginnings, they climbed to the top, securing one of the biggest deals in music history and leaving an indelible mark on the industry.

This documentary not only features insights from hip-hop greats like Eminem, Snoop Dogg, and Ice Cube, but it also offers valuable lessons in perseverance, innovation, and the power of collaboration. The Defiant Ones is a reminder that success often comes from embracing the unconventional and staying true to your vision.

6. 14 Peaks

14 Peaks follows Nepali mountaineer Nimsdai Purja on his quest to summit all 14 of the world’s 8,000-metre peaks in just seven months—a feat that should typically take seasoned climbers seven years. This documentary is a thrilling exploration of courage, determination, and the power of letting go of fear.

Purja’s story is about breaking boundaries and achieving the impossible, a message that resonates deeply with anyone striving to leave their comfort zone and tackle big challenges. 14 Peaks will inspire you to push beyond your limits and pursue your goals with fearless determination.

7. Bezos

Bezos offers an intimate look into the life of Jeff Bezos, the founder of Amazon. This documentary explores how Bezos identified a problem, created a groundbreaking e-commerce solution, and built one of the largest tech companies in the world. It’s a story of vision and relentless pursuit of innovation.

For those in the tech industry or anyone providing solutions, Bezos serves as a powerful example of how one idea can change the world. It’s a reminder that with the right mindset, you too can create something that leaves a lasting impact.

Final Thoughts

These seven documentaries are more than just entertainment—they’re sources of inspiration, packed with lessons on perseverance and the power of believing in yourself. We hope this watchlist motivates you to up your game and face any challenge no matter how big it seems.

Have any other documentaries that have inspired you? We’d love to hear your recommendations. Share them with us on any of our social media channels.

And before you dive into this binge-worthy list, remember that with the Geegpay virtual dollar card, you can easily subscribe to your favourite streaming platforms like Netflix, Prime Video, and YouTube. Creating a virtual dollar card on the Geegpay app is quick and easy, and costs only $3. Download the Geegpay app to get yours now.