Over the last decade, I’ve lived globalization, entrepreneurship, change and crisis, complexity and chaos. I must have run into at least a dozen intractable, impossible, show-stopper, nerve-racking, all-or-nothing situations and at least several orders higher magnitude wicked problems. I also ran into the entire spectrum of human behavior, what the Clint Eastwood character would call the “good, the bad, and the ugly” (I would actually add the “irrational”).

About five years ago I also started an in depth study of the cutting edge thinking related to complexity and disorder. Finally I also studied and noted my own behaviors and responses in such circumstances; like Hansel and Gretel I traced my steps into the wilderness in case I ever had to find my way back. This ability to not only act but rationalize the act has served me well, substantially increasing my awareness and lowering my stress when faced with the new and unfamiliar. It has also resulted in a problem solving and sense-making body of work which I think rivals the best of what’s available on the market. I have yet to capitalize on all this, but I have learned to be patient.

So how does my track-record of dealing with and rationalizing the ambiguous help me when I encounter the next intractable situation, the next problem of finding a pattern when there are no “beacons” to orient myself, no supporting evidence, and no prior knowledge? The answer is, “it all depends”. Even though I have every reason to be confident, I approach any new intractable situation with due respect, and with guarded confidence – much like an experienced circus trainer approaches a ferocious animal. On one hand I know I’ve solved intractable problems before, on the other I know that “intractable” may indeed mean unsolvable this particular time. Just because I’ve done ten successful strategies in ambiguous circumstances doesn’t mean I’ll get the eleventh one right.

What this apparent lack of confidence allows me to do is to balance two opposable perspectives that form an apparent paradox: “know lots” and “know nothing”. I try to tame the intractable problem with some of the thinking I’ve used before, but don’t expect it to necessarily work. I also approach the intractable problem from the opposite end: the “know nothing”. I force myself to forget everything I know and just allow my mind to try to make new connections. This is excruciatingly hard and it comes with an overwhelming sense of relativity which is psychologically very difficult to deal with. It’s that feeling of starting from scratch that I think only great artists must understand: how do you tackle the next painting after Mona Lisa? But it’s this discomfort that one has to live with continuously if one is to keep an open mind. It’s also the continual risk of saying “it all depends” even as the competition proposes something straight forward and reassuring.

Art comes to mind as the best example of the open mind – experience balancing act.  On one hand learned techniques are essential and distinguish the artist’s personal style, on another each new art piece is unique and distinct from all others. In this sense, Roger Martin’s design thinking, Dave Snowden’s context relative sense-making and Russell Ackoff’s idealized design and views on aesthetics reinforce my assertion that wicked problems solvers are true artists. They have mastered not just the techniques, but the psychology of continual renewal and learned to live with a healthy dose of discomfort. They are comfortable with the feeling and knowing that “it all depends”. Are you?