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Review | Generation: Freedom – How the Internet killed the day job

This powerpacked documentary will make you jump the fence and go for your dreams

Rating: 3.5 out of 4.

One of the numerous strengths of Shohawk Films’ documentary “Generation: Freedom” is the visceral punch it packs. It boasts a profound idea. It has a bunch of gritty human beings at its center, an amass of intellectual themes and boatloads of inspiration.

Filmmakers Michael Hall and Christopher Sakr have managed to put together a brilliant piece for would-be entrepreneurs, especially, those sitting on the fence. Their documentary features 16 online entrepreneurs, who chose to turn their lives around and rise above the drudgery of the rat race.

The literary world is awash with motivational and how-to literature on entrepreneurship. The likes of Gary Vaynerchuk, Daymond John, and many others have built upon their success in business by writing bestsellers.

With “Generation: Freedom”, Michael Hall and Christopher Sakr tread into the far-from-saturated space of documentaries for entrepreneurs.

Told in a linear manner and using extensive interviews, “Generation: Freedom” places you into the middle of the action, leaving you to wonder why you can’t take the plunge.

It answers existential questions that often give many the sleepless nights. What is my life’s task, what ideas can I build a business around, am I good enough to shun my job and start up on my own?

Though it doesn’t claim to have all the right answers, it does nudge you in the right direction with motivational stories of those who have been down that road and pulled it off.

Paula Pant Generation Freedom
Paula Pant

Most of the upstarts in the documentary are running a ‘microbusiness’.

Podcaster and blogger, Paula Pant, defines it the best. She declares, “I see a microbusiness as a business not intended to be scaled to attract venture capital. It’s typically bootstrapped and usually built for the purpose of supporting yourself while you enjoy your lifestyle”.

She also turns out to be the one who has the most actionable pieces of advice to offer.

As you hear from these entrepreneurs, you feel a nonpareil sense of freedom they exude. For most entrepreneurs, freedom to work on your own terms and achieving your full potential are the biggest driving factors.

Cole Cuchna, the founder of the Dissect Podcast, says, “I felt like I had more to give which I wasn’t able to give at my job.

Pat Flynn of Smart Passive Income gleefully shares that he and his wife often drop their kids to school, much to the amazement of everyone. Paula Pant says, “It gives you the freedom to clean your house at 1 PM on Wednesday.” J

The documentary mainly addresses two thorny issues:

  1. How to Start an Online Business?
  2. How to Sustain an Online Business?

The first one mostly perturbs the aspiring entrepreneurs needing direction in their early days. The second problem and its fruitful resolution are crucial for the existing business owners who have started and now must stay afloat.

The inspiration and wisdom flow nonstop in its 1hr38 mins of runtime. I managed to glean a few important lessons from Generation: Freedom which I am sharing below:

#1. Passive Income is dope

Generation: Freedom untangles a lot of knotty questions for the entrepreneurs to overcome their initial fears.

Buoyed by dreams of attaining freedom and lifestyle they desire, many entrepreneurs often grapple with the conundrum of how to make money online. To decipher this, the documentary sheds light on revenue generation models, SEO, paid ads, etc. All these avenues can unlock the doors to passive income.

Paula Pant, who is as enlightened as she is charming, defines Passive income as money that comes in without any direct correlation to time. She quite aptly underlines that passive income is obliterating the link between time and money.

Stephen Chou who helped his wife set up an online business, however, makes gives an important suggestion. He says, “It’s easier to start a business while working full time then it is to just quit cold turkey and then start a business.” Basically, start something on the side, build it to the point where you start to earn a decent figure and then entertain any thoughts of giving up your 9-to-5 job.

#2. Build your Personal Brand

Chris Ducker Generation Freedom
Chris Ducker

Chris Ducker, blogger and now the bestselling author of “Rise of the Youpreneur“, declares, “Three to five years from now, this (personal branding) will be an extremely widespread, lucrative business model.”

No wonder Chris has his guns trained on this space; his online business entails training for building a personal brand.

Motivational podcaster, Niyi Sobo, shares an invaluable strategy he used to put his personal brand on the growth trajectory.

He would interview influencers on his podcast and those influencers then shared the podcast with their set of audience. This simple yet effective move helped him gain followers and grow his brand, both.

#3. Delegate, Delegate, Delegate

A big part of enduring in business as per the advice of these small business owners is the delegation of responsibilities. Once your business has crossed the initial milestones you can’t be doing everything.

Chris Ducker shares one of his best practices. As an entrepreneur, he says, he listed down the things he hated doing, things he struggled doing and things he thought as a business owner he should not be doing and outsourced/delegated accordingly.

Online illustrator and entrepreneur, Lisa Congdon, calls it right down the middle, “Paying someone else to do something can be a better use of money when you have reached a point where you have only limited hoursin a day.”

John Lee Dumas, podcaster at Entrepreneurs on fire (he also features in Gary Vaynerchuk’s latest bestseller “Crushing it), notes all he does is record a podcast. His team does the rest. From creating a blog post, doing the creatives and distribution, etc, everything is delegated.


#4. Reasonable goals & high productivity are a must in early days

When you are running an online business on your own, it is important to set yourself up for success. The easiest way to do that is to have reasonable goals. Not having reasonable goals can shatter entrepreneurs’ dreams of doubling revenues and growth.

Insurance blogger, Chris Huntley remarks, “People often set grandiose goals and then get buried under their weight“. His curt yet emphatic advice to other entrepreneurs: Break the goals down.

John Lee Dumas reflects on a couple of productivity tools he puts to good use:

  • Pomodoro Technique. John Lee Dumas is a huge fan of the technique. It requires you to break down your day into 25 mins intervals so that you focus and get into deep work mode. Basically, block everything out and focus on knocking stuff out in that time frame.
  • The Pareto Principle. Dumas suggests doubling down on the endeavors that yield the maximum output and slowly, zero in on the top 2%.

#5. Stay focused and put in the hours until the business is profitable

Aaron James Draplin Generation Freedom
Aaron James Draplin

There are some nuggets of advice in this feature that will stick with you.

Towards the end of the documentary, while mooting sustainability of the business, Aaron James Draplin, founder of Draplin Design Co. affirms, “If you hustle and you are frugal, then you’ll get ahead.

It’s hard to disagree with him. If you expect to strike oil in the first month of starting an online business, you might be in for a rude shock. Many bloggers, podcasters and YouTubers virtually see 6-12 months of barren vistas before earning decent figures.

The idea is to stay focused, put in the hours and let things happen. Cole Cuchna states, “An act of creation or publication puts me in a position to have luck.”


Finally, “Generation: Freedom” proves to be invigorating documentary filmmaking. Online business is in a continual state of evolution and it will stay that way for some years to come. Says Lisa Congdon, “If you have a passion and you are really dedicated to your passion, then you can create a job and live a life that some people view as a dream life.” It sounds cheesy but is absolutely true.

Generation: Freedom, Official Trailer

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