First, please explain what ‘unschooling’ means.

Unschooling is an education philosophy that accepts that we humans are intrinsically interested in learning. The idea is: if you take away the structure and forced learning that the modern school system imposed on children, they will learn much quickly and more effectively. They’ll pursue subjects that they’re actually interested in learning about, and grow up to be much more effective at the subjects which they actually care about.

The modern school system, in my opinion, is all about cultivating mediocrity. We take kids and force them to learn a specific set of knowledge that everyone must learn to pass onto the next grade. This doesn’t take into account, at all, the huge range of available knowledge in the world. The truth is that some people are better at some things than others. I was incredibly good at reading, writing, tribal leadership on the web, web publishing, from a young age.

Unschooling allowed me to spend many of my waking hours, and even late into the night, practicing what I was interested in, instead of what some bureaucrat somewhere decided that I should learn to be successful.

Schools teach you to follow the rules, and do what you’re told. They teach you that everyone should be the same, and fit in. The reality of the world is the most successful people don’t do what they’re told, and they don’t fit any one specific mold. Why would you want to be like everyone else, if you can be so much more successful by being different?

What age or grade did you stop traditional schooling?

I went to kindergarten, I left. When I approach high school age, I’d decided that I wanted to try school again, so I tried 9th grade and left because I was spending most of my days learning basic information on a variety of topics — most of which I cared nothing about. In 9th grade, there was a dance class that I started to take at the school that I enjoyed immensely — as it was one of the most challenging subjects being taught at the school.

So, instead of going to 10th grade, I started taking anywhere from 7 to 18 dance classes a week at a local dance school and rapidly excelled at ballet and modern dance over the next few years. I wouldn’t have been able to do this if I’d been in school, because I would have been forced to learn algebra instead of doing what I wanted.

What was your average day like (schedule, activities you participated in, etc.)?

The thing about unschooling is there is no average day, there’s no schedule. You do what you want when you wanted to do it. Some days I’d spend entire days coding websites, writing blog posts on Livejournal. Other days I’d spend hours choreographing dances, or taking dance classes, at the dance school that I spent a lot of time at. By the second year of dancing, I’d started contributing so much value to the dance school (by helping with upkeep and general culture around the school) that I no longer had to pay for classes.

I’m not saying that to boast, it’s just that when you have a free schedule you can find ways to support yourself and your work that doesn’t involve trading time for money, or time for education and so on.

What mattered most to me was to do what I was actually intrinsically motivated to do every day. If I didn’t want to work on a website, I wouldn’t. If I didn’t want to go to dance classes, I wouldn’t. The thing is, when you get beyond the initial stages of learning a skill, especially one as difficult as dance, you start to enjoy doing it way more than you enjoy not doing it. When you enter this sweet spot of actually enjoying doing the work (which I don’t believe many kids in school ever get to, because they’re shuttled around every 45 minutes to a new subject that they don’t care about), you can spend hours working on the subject until you’ve achieved a complete level of mastery. Daniel H. Pink describes this in more detail in his brilliant book Drive: The Surprising Truth About What Motivates Us.

Is there anything you feel you missed out on by being unschooled?

One of the biggest challenges I had was socializing. I just didn’t have many friends for most of my childhood, which I think was mostly because I was on such a different schedule than everyone else. Most of the kids had friends from school. There weren’t that many people my age engaged in the way that I was with places such as the dance school and other locations that I was hanging out at. Most of my friends were a lot older than I was, but it’s hard to go hang out at a coffee shop with a 14 year old when you’re in your mid twenties, you know?

I’ve read on your blog that you graduated from New York University. What made you decide to attend a traditional four year university after being unschooled?

By the time I reached the age to go to college, I was hell bent on getting out of Chicago, and college seemed to be the best venue to do this. College was a great experience, I met a lot of truly remarkable people there. I think I learned a couple of things as well. I was enrolled in the first class on blogging that NYU’s journalism school put into place with William Patrick Phillips, the author of I Want Media, this led to my getting an internship with Gawker Media for a summer, and which led to my getting hired on at New York Magazine when they launched their blog network.

I escaped after three years, because being in college for four just seemed way too long. I had all of my required courses wrapped up, so I just went ahead and graduated. This saved a lot of time and money, in my opinion.

It all seems to make sense in hindsight, but that’s how these things work out.

In all honesty, my biggest problem with the college system is how much money it costs vs. the value that is provided by the institution. I’m not convinced that all of the money that went into educating me during the three years was worth what I got in return. We used to go to college because that was honestly the only way to obtain information, so it became the single most important measure of how much a person was worth. These days though, information is freely available to anyone. Seth Godin had a post on this a few days ago that rang very true to me.

I know plenty of people with masters degrees who don’t know anything. I know plenty of people who never went to high school who know far more than anyone I went to college with. What college you went to has no barring whatsoever on how intelligent or how valuable you are as a person.

How do you feel unschooling shaped your life today (positive, negative, etc.)?

I can’t see any negatives, in hindsight. At the time I really wished I had a girlfriend pre-college, but doesn’t every teenager? In hindsight, whatever. No one keeps track of the people they knew from high school anyway.

The positives: I have an incredible ability to intrinsically motivate myself to accomplish goals that I set for myself. I developed a skill set when I was high school aged that formed the basis of the work that I do now.

We’ve been conditioned our entire lives to follow the same ‘secure’ path: graduate college, find a job with a large company, retire 45 years later. That’s why when we’re faced with entrepreneurs doing their own thing, we freak out and label them as unnecessary risk takers. ‘It’s too risky’ is the lazy argument to make because it relies on false logic we’ve been forced to believe since we were children–that working for the man is the most secure way to achieve financial solvency.

So let’s debunk the myth that entrepreneurship is risky. What we’re actually afraid of is control and the responsibility that comes with it.

Just think about it: what could possibly be more secure than having full control over your business? ‘Risk’ is something that exists when you don’t have control over a situation (i.e. working for the man). I’m not sure how the argument against entrepreneurship exists when faced with the fact that control and risk are inversely related. We all want more control of our lives, yet most of us continue to show up for our 9-5 jobs, where control and decision-making are nothing more than facades.

Face it: when working for the man, we have no control over whether or not we receive raises or bonuses or get fired. We like to believe merit is enough to receive that promotion, but as was made evident by the recent economic meltdown, hardworking and deserving individuals lose their jobs everyday. We sell our souls when we choose to work at a place where we don’t have say in what happens. Our livelihoods can be destroyed without warning for something as vague as ‘cost cutting.’

Entrepreneurship solves these problems. Unless you fire yourself, you won’t ever lose your job. Logically, what is more secure than having complete control of your life? If you couldn’t figure it out, the answer sure as hell isn’t working for the man!

Emotional solvency

I’ve only mentioned the ‘security benefits’ of entrepreneurship. I’ve yet to touch on its emotional benefits, which could be a whole article in and of itself. The problem with the outdated ‘secure’ path (college -> job -> retirement) is that it only takes into consideration financial solvency. Entrepreneurship solves the problem of what I call ‘emotional solvency,’ or being happy and passionate about your work life. We’ve been conditioned to think working for the man in a mundane job is how life is supposed to be lived. Let’s face it: life is short, and as Glen Allsop so eloquently puts it, we all die at some point. Doesn’t it make sense to pursue your passion and live happily rather than force ourselves through another 9-5 day?

Yes, entrepreneurship is difficult and requires a tremendous amount of hard work, yet it’s completely rewarding. The thing is, when you chase your passion, working 12 hour days doesn’t feel like work. And better yet, if you work hard enough, you–and you alone–enjoy the fruits of your success; screw those tiny end-of-the-year bonuses!

So if you’ve always considered branching out on your own, I say go for it. People who you love and are close to will surely call you crazy and try to prevent you from taking “unnecessary risks,” but as the saying goes: It’s often easier to ask forgiveness than it is to ask permission.