Generation Freedom Inspires and Motivates

Recently, I had the pleasure of viewing the full screening of Generation: Freedom. The documentary, which retails for $19 and has a running time of 1 hour and 39 minutes, is the brain child of Michael Hall and Chris Sakr. Michael shares his story, describing how he went from a job he once loved to one he was forced to endure, thanks to a company buyout. He discovered one of my favorite bloggers/podcasters, Paula Pant, of Afford Anything, on a long drive home and was hooked by the idea of financial freedom. Michael and Chris soon set out on a mission to interview people who had achieved financial independence, largely through the powers of the Internet. Generation: Freedom is the result.

About the Documentary

I’m a big fan of documentaries, and since I’m all about financial independence, I was eager to watch the film in its entirety. Michael and Chris conducted 17 interviews with some well-known personalities, including Paula Pant, John Lee Dumas (Entrepreneurs on Fire), and Stephen Chou (My Wife Quit her Job). And there’s a fair amount of diversity in the sample, from travel writers to motivational coaches to fine artists and furniture makers. The youngest is Brennan Agranoff, who founded his own sock company at the age of 13 (HoopSwagg). There are a lot of ideas waiting for you to steal!

Generation: Freedom Trailer

The documentary segments the interviews into the steps entrepreneurs use to create a successful online business.

  1. Find your passion
  2. Pick an income stream
  3. Find your audience
  4. Test your idea
  5. Begin
  6. Grow

Generation: Freedom as a Practical Guide

My expectations of documentaries related to personal finance are that they not only provide information, but offer useful strategies and tools that viewers can implement in their real lives. By this measure, Generation: Freedom lives up to the challenge. The documentary is particularly eye-opening for those just beginning to explore online money-making opportunities. There’s some great advice in terms of finding an audience, setting goals, and managing time…and some helpful acronyms.

  • PLAN – What are your target audience’s Problems? How do they talk about their problem (Language)? What kind of Anecdotes or stories can they relate to? Is your solution aligned with their Needs?
  • GPS – What is your Goal? What is your Purpose? What Strategies can you try to reach your goal? Break your large goals into manageable time increments – weekly, monthly, quarterly, annually.
  • Focus on the 20% of your effort that produces 80% of the results (Pareto Principle). Use tools, like the Pomodoro method, to maximize productivity. Outsource work so that you can concentrate on the critical tasks that require your unique skills.

Inspiring Stories Prompt Action

Information and tools can help readers create strategies, but they don’t inspire on their own. And that’s where Generation: Freedom excels. We get to eavesdrop on conversations with some wildly successful entrepreneurs. And from them, we’re reminded that entrepreneurship is hard work and success seldom arrives overnight. And for many of our featured innovators, their introduction into the brave new world was the result of a dysfunctional workplace or the loss of paycheck. That fact alone is enough to inspire people who are miserably enduring their job because they feel they have no other choice.

Passion plays a major role in their success stories. One of the challenges we face when starting out is identifying our own superpower – that thing that makes us unique. And once identified, it’s not always easy to figure out how to market it. Perseverance is one of the strongest traits of those interviewed. They did not give up when things got tough. For example, Megan Wristen stuck with it for eight years before she began seeing a profit from her blog. Experimentation – and failure – is part of the process.

The Internet is one of the few innovations that offer an equal opportunity playing field. Sure, it requires some smarts, technical skills, and money to get started, but the Internet door is wide open. And perhaps that’s what is most inspiring about the featured stories. We get the sense that anyone, including ME, can figure this out. And by launching an Internet business as a side hustle, we lessen the risks.

For bloggers and creatives, it takes particular courage to create an Internet persona. Increasingly, the product we sell is ourselves. It’s our personality, our art, our writing style, our philosophy that draws people to us. And that opens us up to criticism, which is rampant in the anonymous online world. It’s easy to get caught up in the negative comments that are inevitable. But the rewards for bravery are immense. In the end, it’s about creating a lifestyle that allows us to live out our dreams.

It’s the inspirational stories that really draw us into the Generation: Freedom, and the production team should be congratulated on capturing such rich and varied voices that truly inspire and motivate.

Production Notes

The content of the film is solid. But there are some annoyances that serve as unwanted distractions.

  • The introduction, with its emphasis on the transition from printing press and assembly lines to the Internet and entrepreneurship, is lengthy and doesn’t generate a lot of enthusiasm.
  • The audio track that runs in the background is distracting. It’s more appropriate to my candlelight yoga class.
  • A computerized voice introduces each new segment, which takes away from the personal feel of the film.
  • The film is interrupted by that same voice reading vocabulary definitions as a dictionary excerpt is displayed. And really, do we need a definition for “information” and “product”?

Together, these production decisions resulted in a more stilted film than desired. While they detract from the quality of the final product, they aren’t enough to dissuade me from watching the film from beginning to end.

Teacup Rating

I have my own special rating scale – the teacup scale. Here’s the crux of it. If you want to escape the workplace, or you lose your job, how helpful will the information in this documentary be to you? On that scale, Generation: Freedom gets a whopping 4.5 out of 5 teacups. Terrific content! The production distractions keep it from the perfect 5 teacup rating.

It’s a documentary I will highly recommend to people who enroll in my Early Exit Academy courses. The film offers practical information and the stories are truly inspirational.

About the Author Brenda

Dr. Brenda is a financial coach, educator, researcher, and sociologist. In addition to blogging at The Five Journeys, she is the founder of the Gutsy Women Club. Her passion is guiding people on their journey to financial freedom through coaching at DrBrendaMoneyCoach and online courses at