Creative problems are rarely well defined. Whether you’re an artist, a scientist, or an entrepreneur, when you’re creating something new, you have to deal with a lot of ambiguous problems.

Nowhere is this easier to see than in entrepreneurship. When sales go down, you have to figure out why. Is something wrong with the product? Is it the marketing? Or did your competition just make a surprise move? You need to find a solution when you’re not even sure what the problem is. The problem is ambiguous.

Ambiguous problems are exhausting and frustrating. Growing up, schools gave us thousands of multiple choice questions, but never taught us what to do when we don’t know what to do.

This is almost daily life for the creative person. If you solving a problem that’s never been solved or if you’re building something that’s never been built, then there isn’t much advice people can give you. You’re often the only one who’s ever asked the questions your asking. The world can’t give you a black-and-white answer.

This is why being able to tolerate ambiguous, ill-defined problems is so important to creativity. People with a high tolerance of ambiguity tend to be very good at the early stages of the creative process. They’re more comfortable with not knowing the answer right away. They’ll allow themselves to have more questions than answers. They’re OK with having a wide variety of options to choose from. All of these benefit our creativity.

In fact, the only real downside to having a high tolerance for ambiguity is that it came make it hard to find closure sometimes. Sometimes you can be TOO tolerant, you can be just a bit too OK with gray areas. This is why creative people often have a hard time finding closure and deciding when to finish a project.

I struggled a lot with ambiguity while I was writing Playfully Inappropriate. As a stand-up comedy teacher, I always pushed people towards using their natural sense of humor. I was always searching for a way of teaching comedy without teaching highly structured jokes. I wanted my students to be funny in a way that was indistinguishable from their natural, everyday, conversational humor.

A few years back, I stumbled upon the most genius scientific theory for humor that I’d ever come across. It was called Benign-Violation Theory. Unlike other theories of humor, it was able to handle everything I threw at it. I tried to find the most bizarre forms of humor possible. To this day, I still haven’t found any exceptions. It’s the closest thing humor researchers have to a universal theory of humor. I knew early on that the theory was something special. I had no idea what to do with the theory. All I knew is that it worked and that no other comedy teachers were taking it as seriously as I was.

For the next 9 months, I created new writing strategies using the theory. I had to throw away traditional stand-up comedy ideas and start over. I was both inspired and frustrated at the same time.

I wasn’t sure where I was going, what I’d find, or if people would even value it. Everything was ambiguous. I had explored so far from the conventional stand-up comedy training industry that I was no longer able to receive help from others. It was an apples-to-oranges comparison. One comedy teacher actually told me that it was “a neat theory that would never work.” I also reached out to Dr. Peter McGraw, the humor researcher who came up with Benign-Violation Theory. While he gave me some encouragement, it also became apparent that I was still on my own.

I lost track of the number of rewrites I made a long time ago. If I’m honest, the first version was a disaster. The writing system was complex and disjointed, and it only achieve its goal a fraction of the time. But each subsequent version of the course slowly fixed these problems. By the time the book launched, what started as a Frankenstein idea had evolved into something that felt natural and authentic. Each version of the book cleaned up some of the ambiguity.

You should always expect ambiguous problems as a creative person. The more you value uniqueness, the more you’ll struggle with ambiguity. That’s just the nature of creativity. You don’t know what you’ll find when you explore the unknown, but setting out on the adventure is one of the most important acts you can take as a creative person.

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