Published on Oct 03, 2020

Knowing where the line is


I love stand-up comedy. It’s amazing to see an artist that masters their art on stage. People laugh because a joke is funny. It’s the purest expression of real time feedback. You’re either funny or you’re not. I can’t imagine the feeling of bombing and an audience not laughing.

For a comedian to be funny, they need to push against the line of what is expected. Oftentimes, that line brushes up against what is socially acceptable. The challenge with this line is that it’s always changing. What was acceptable five years ago can be deemed inappropriate today. For instance, my favorite movie of all time is Pulp Fiction. There is gratuitous use of racial profanity that back in the 90s didn’t cause too much trouble. Watching some of those scenes again today is cringe worthy.

Coming up with insights

The parallel I’m trying to make is just in an artistic endeavour that breaks through the line, an insight is needed. A comedian uncovers a funny joke by going right up against what is seen as normal & acceptable.

An early stage company doesn’t break through easily by coloring inside the lines. It has to go right up against what is known and what works today. My analogy still needs some work but it’s the image that I’m trying to convey.

In both cases, an insight is needed as to where the line is and also where it is moving. A company doesn’t easily succeed by copying what’s been done in the past. It has to innovate. Sure, it can copy but a breakthrough success needs to go right up against the line.

Pushing against the line

Just like in comedy, this is where knowing where the line is can also backfire. Saying a joke that was acceptable a few years ago will most likely backfire today. For a startup that hasn’t achieved product-market fit, going over the line most likely means that the idea won’t work. Perhaps it’s time hasn’t come yet.

This can be a useful guide for companies that need to innovate. It means they can’t stay stuck with what is always expected. They need to continuously push against the line and improve.

The line is of course always changing and that’s the hard part. The job of a leader (or artist) is to scan the environment and know not just where the line is, but how to go up right against it.

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