This is how the seminal exercise in Drawing on the Right Side of the Brain works: you take a drawing, turn it upside down, and then duplicate it. Instead of looking at it as "draw a nose, then draw eyes" you have to refer back and forth to the drawing, again and again, because it becomes a collection of lines and intersections. Through this exercise, you begin to see the world as lines and connections while you're drawing.

I'm not talking about "thinking outside the box," which is tame by comparison. As long as you respect the box, you're still beholden to it, whether you're inside or outside. It's relatively easy to think outside the box because the box gives you a lot of structure and comfort; all you're doing is variations on a theme.

I don't mean "upside-down thinking," which often occurs during the so-called debates of our country's policies (example: "Keep your government hands off my Medicare").

I'm talking about doing something much harder, which is to question everything. This is both difficult and disturbing -- your brain fights these kinds of inversions using (what it thinks is) cold logic, which is more likely to be a simple fear reaction.

Here's a relatively simple example: In Tribes, Seth Godin tells of a restaurant in New York which is only open about 20 days a year, on Saturday nights. You keep track on the web of when it's happening and what they're serving that night, and make your reservation. The idea of it is outrageous from the standpoint of the restaurant business model, but apparently it's quite successful; going to one of these events is more like going to a party than a restaurant, and the people running it aren't the typical restaurateurs run ragged by their business.

On top of books like Freakonomics and those by Malcom Gladwell, I have had two upside-down experiences which have caused me to start questioning and wondering about everything we "know" to be true.

The first has been Open Spaces Conferences, which I've talked about in numerous other posts. I tried to create a different kind of conference on my own, but all I did was work around the box of existing conferences. The shift happened when Martin Fowler suggested we try this completely different way of thinking about conferences. The upside-down factor in this case is "what if we let attendees spontaneously design their own conference?" It's very hard to think this way because everything you know about conferences gets in the way, and you quickly get lost in details of why it won't work. This is where it's very important to keep the brainstorming and specifications about what we want to achieve separate from implementation details, otherwise your brain gets gridlocked. And on balance, until you come up with a mechanism to implement your idea, it can seem totally impractical. It's very challenging, because it involves social engineering -- figuring out ways to leverage self-interest so that people want to do the right thing.

My second experience has been with Burning Man, where participants create the most amazing city in the world, for one week out of the year. Black Rock City is the only place I've seen (so far) that I would live in other than Crested Butte. The first time I went, I spent a couple of days being stunned, in serious culture shock, because I never imagined such a place could exist.

And now I think I'm trying to invent a new business model, and running into the same kind of brain-rigidity that I did with conferences. Actually, I feel a bit more flexible because of the previous experiences, and I'm actively looking for things that I might be able to turn upside down. But it's hard, because we are so schooled in conventional-think from day one, all through school and in most businesses. There are workshops and experiences that can help loosen you up (improv, for example) but I've never heard of anything that specifically focuses on freeing your brain. Wouldn't that be something. If I knew how to do it, that's a thing that would get me excited about giving workshops again.