One of the hardest writing lessons I ever learned was also one of the most amazing lessons I ever learned, and it was in two parts.

The first part was that being a standup comic is hard. Doing improv is comparatively easy, but walking up onto stage and doing standup is just… brutal (and I can tell you exactly why that is, now!). Comics aren’t people who walk up on stage and be funny so much as they are fantastic actors playing the part of a comic who walks up on stage to be funny as if it’s the most natural thing in the world.

The second part I learned was a writing lesson, and that every joke, every line, every paragraph is written and rewritten a billion times, and exact word order matters (my girlfriend Quinn [also a great stand-up] lent me a copy of Zen and the Art of Stand-up Comedy). A joke can fly or fail based on transposing even two words. A joke, a bit, an act all contain parts and the parts have to be in the right order in order for the joke to succeed. Two people can tell the exact same joke and one tells it brilliantly and the other flops. It’s all in how it’s written and how it’s delivered (because timing is part of writing, too…


The reasons these lessons were so hard was because I wanted the process to be fluid. I wanted the process to be organic and flowing and natural and brilliant.

The notion that there was a mechanical structure underlying successful comedy felt wrong to me, felt like I was being shown the closet where all the Christmas presents were hiding before Mom and Dad wrapped them and marked them “from Santa”. I almost felt betrayed.

But then I started listening — really listening — to comics. When they were funny, I saw the structure working. When they weren’t funny, I saw them violating the structure.

Some just seemed to have a knack, and others floundered.

I also started spotting this in comedy writing of my favorite columnists.

So I swallowed my feelings of betrayal and started really looking at how I structured gags. I started placing elements in certain orders.

And it worked.

Holy christ in a blender — it worked! Getting things in the right order worked!

Now, I’m not going to say I’m a brilliant comic now. I haven’t been up on a stage in ages, and when I was, I had some very clever moments, but a ton of inexperience, which resulted in some spectacular failures (I destroyed the evidence, thank what gods exist!).

But this lesson was about more than comedy. It was about how I present ideas, how I write, how I speak. On any subject.

And then I started seeing patterns in my interactions with other people. And interactions between third parties.

I… I was stunned.

And yet intrigued.

My current state is “Holy chrome, I’ve still got so much more to learn!”

I don’t think that’s a bad state, honestly.

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