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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.

  • Brad

    Great post Blake! I can relate… I’ve passed on all the paid services for “learning to code” as there are so many resources I can use that are free.

    Also, having community and people that you work is what makes work fun. Something I’ve found I greatly miss working alone.

  • Scott Noelle

    This is a bold admission, Blake. And I wonder if you are, to some extent, throwing out the baby with the bathwater.

    You’ve already mentioned the “baby” aspects, which include not only freedom from wage slavery but also enabling people who can’t afford working with you face-to-face to benefit from your gifts in a way that also supports your continued giving.

    me, the “bathwater” aspect of freedom businesses — a-la Tim Ferris,
    Brendon Burchard, and other internet marketing gurus — is that their
    models ultimately depend on your willingness to reduce people to numbers
    and/or pretend that your relationship with your customers is more than
    it really is.

    A few years ago I paid a shit-ton of money for a
    membership program with one of these “relationship marketing” gurus
    thinking he really cared about my success — not me personally, but in
    general — only to realize that he cared only enough to keep me
    interested in his next high-priced program. He did the minimum necessary
    to deliver on his promises. And I’m supposed to model my business after
    that? No thanks.

    My “freedom” business doesn’t give me tons of
    free TIME because I do care about making a difference for lots of
    people, so I invest a lot of time on that. But I’m free in the sense
    that it’s my choice to spend my time that way. And when I need more
    face-to-face connection with the people I serve, I can restructure my
    “virtual” services to accommodate that.

    If you formed a
    membership community who paid you modest monthly fees to get a little
    more than you already gift to the world for free, I have no doubt that
    you could still focus all the time and energy you want on face-to-face
    work like Unschool Adventures AND serve your online members easily by
    letting them in on your insights from the face-to-face experiences —
    for example, via a members-only blog or private Google hangouts.

    Not saying you *should* do that, but that you could if you wanted to.

  • Blake! I saw your website listed on and ended up at this post.

    Though I do my best to stay away from recurring memberships, I spend a considerable amount on online courses each year. I just look at them as an education expense, and as a new way to compensate teachers.

    I’ve also been involved with producing and marketing natural wellness online courses through working at Floracopeia. My experience is that online courses are often an easier way to get the teachers’ messages to more people, and the income it provides allows the teachers to further their work instead of always just trying to spread the first level of their material.

    However I totally get your points about why you’re not feeling in integrity with the subscription/course gig, and there’s definitely a lot of shadow to the industry. The market is also increasingly saturated, as everyone wants an easily produced digital product to peddle. However, I still think there’s a lot of opportunity for people who figure out how to reach their market with the right message and product. My question for you is… maybe there’s a different way that you could present your material that feels genuine to you? Like what if you taught the material live and interacted with students? What if you cultivated the same community experience you loved, but through webcast? Or, what if the whole online thing was free as a way to build community and momentum before an in-person event–could the online work make in-person experience more impactful?

    • Thanks Alex, these are really good thoughts and suggestions! Especially the questions at the end. Got me thinking…