Freedom Businesses

I have a dream that needs to die.

Ever since reading The 4-Hour Work Week in 2007—a book that influenced an entire generation of entrepreneurially-minded, recession-affected young adults like myself—I’ve dreamed about starting an online “freedom business.”

A freedom business typically looks like this:

  • You can run it online from anywhere in the world using your laptop
  • It often relies on automated technologies that provide “scalability” and let you remove yourself from the equation
  • Once the gears are in motion, profits happen easily and generate so-called “passive income”

Think of an online t-shirt business that outsources all of its production to third parties. Or a Kindle book, a monthly membership community, or an iOS app. If the owner sets things up intelligently, hires a little help when needed, and keeps the marketing machine going—she has herself a freedom business. It’s an attractive idea.

“How can I combine my passion for education, self-directed learning, and unschooling with the freedom business model?” I’ve asked myself approximately a dozen times in the past few years. I dream up a new idea, get really excited, and create a new website to flesh out my ideas. A few recent examples:

[Note that none of these programs are active, although they might look like it! That’s just how my mind operates—I need to flesh out the final product on the web to really get a feel for it.]

Sometimes I throw one of these out to the world to see if they’ll bite, like I did with LaunchPad, which failed to draw sufficient interest. But more often, I simply lose steam for the idea, because I realize that neither I nor anyone I know pays for online communities or courses.

Sure, I know that some people pay for things like this. Josh Ship sells access to his teen mentoring videos for $19/month. Julie Bogart offers her highly-regarded BraveWriter courses to homeschooling families. LocationIndie offers a worldwide community for location-independent business owners, and Fizzle does the same for budding entrepreneurs.

I feel like my freedom business ideas are backed by positive intentions: I want to increase the number of kids who find success outside traditional education in the world, I want to offer my services at a lower price than my a la carte private coaching, and I want to provide coaching in a group environment so that I don’t feel like I’m repeating myself with individual clients.

The problem is: I’ve never bought into the value proposition for a paid online community or course, so why should I expect others to do so? Whenever I’ve encountered an online course or community that charges $$, I’ve always felt like I can get what I need from the free trail period, find equally good resources for free, or simply felt like it’s not worth it. If I wouldn’t buy what I’m selling, why would the people I’m serving? (A business owner does not necessarily need to be a consumer of his own product, of course, but it feels like an integrity thing to me.) 

This leads me to believe that freedom businesses are more conceptually appealing than practically appealing to me. I love the idea of creating more freedom in my life, but I’m suspicious that this model isn’t the right way to go about it.

Sometimes I have to pinch myself and remember that I’m already doing a good job of building freedom into my career. Unschool Adventures is at the point where I can run a handful of trips (3-4 months total time investment) and have the rest of my year largely to myself. (I haven’t been successful, however, in removing myself from the trip-leading equation.) I’m not making much money by my peers’ standards, but I get to live where I want and do what I want. I still dedicate a few hours each day of the off-season to program development or marketing, but it still feels like freedom.

Writing is also a form of freedom business, and for the past few years I’ve been receiving a modest monthly income (approximately a rent payment) from the sales of my books through Amazon. I invested a ton of effort in those projects initially, but now they’re essentially selling themselves with a little ongoing marketing and public speaking on my part. So I’ve got that going for me, which is nice.

So why do I keep coming back to the online freedom business idea? Why does it feel like a virus that’s infected me?

I think it’s because I’m naturally drawn toward systems, technology, automation, and efficiency. I’ve always like the idea of doing more with less: working smarter, not harder. And in the Internet era, creating an almost-automatic, money-generating system has indeed become reality… for a select few. The stories of those select few—as propagated by books like The 4-Hour Work Week—make the rest of us (especially the systematizing ones) feel like suckers if we aren’t doing the same. It’s really another form of keeping up with Joneses with 21st century, globalized, Silicon Valley twist.

The freedom business idea gets a few things clearly right: it feels good to have control over your employment situation, the chance to travel more than once a year, and significant free time to pursue your self-directed learning, interests, and hobbies. That’s what’s really waiting at the end of the rainbow for freedom business owners, and to his credit, that’s what Tim Ferriss was ultimately selling in The 4-Hour Work Week. That positive vision keeps me coming back.

But ultimately, here’s what I think makes freedom businesses a bad idea for me: the most important experiences in my life have involved working face-to-face with people, not a computer screen. Summer camps, international travel, Berkeley and the co-ops: each provided a sense of community and first-hand experience of helping people that’s 10 times more motivating than any online coaching I’ve done. Books have been an important part of my life, too, but largely as tools that connected me (face-to-face) with new individuals and communities.

I don’t feel done with leading groups of young people. I don’t feel done with writing more books and articles. But I do feel done with this  “freedom business” dream.

Time to let it die.



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