Sometimes my dream assignments are the ones I know I enjoy: creating a juicy communications strategy, writing about something I find fascinating, getting sent on an all-expenses-paid trip to the Atacama Desert. (Maybe one of those has never happened.) But sometimes they come as projects outside my comfort zone that end up teaching me a lesson about how pliable that zone’s boundaries are.
For the second year in a row, I was tasked with writing a regular client’s employee awards show script, a project that originally made me quake at the direction to “make it funny.”
This year was so much easier than last because I’d done it before, and they know me and my sense of humour, and I know them and theirs, and I knew that by funny they mean corporate funny, not Ali Wong funny. But the first year brought me straight to my insecure place.
I have a certain sense of humour. I crack myself up often. I make other people laugh occasionally, sometimes even on purpose.
I try to inject some humour into much of my own projects, and what I can for corporate projects. My favourite headline to write was “What the hack is a hackathon?” so that’s my sensibility in a nutshell.
Obviously I don’t write comedy for a living. I know people who do and I am not those people. So the thought of writing a funny speech for the CEO in particular was mildly terrifying.
I thought about his personality: warm, friendly, confident, good-natured, sincere. I sat on the project for a while, mulling over ways to approach it, googling CEO jokes, hoping the hilarity would percolate and come out fully formed. When my insecurities and I sat down to the computer to write, everything came out forced, stilted, unfunny.
Finally I thought about my natural sense of humour. I thought about the time I was asked to give the introduction at a comedy fundraiser for the arts centre where I sat on the board. Why me? No one else wanted to do it and I said yes as part of my mission to push myself outside my comfort zone.
I just had to provide the outline of the event, housekeeping details, and introduce the MC who was also the headliner, but I found the idea of standing up and reading a piece of paper full of boring information in front of 200 people attending a comedy show more terrifying than the idea of being myself up there. I wrote the script to sound like my natural speaking patterns, including some self-deprecating humour, which also made it easier to memorize.
I knew I would come across as nervous-to-petrified, so I leaned into it. Introducing myself, I pointed out “I’m the least funny person you’ll hear from tonight.” I compared myself to Oprah when telling them they’d all get gift bags. I promoted the arts centre classes with some comment about my lack of artistic ability. I’ve blacked out any other memories of the brief speech but I remember getting laughter – I don’t even care if it was pity laughter, as long as it came at the right times to show they were listening — and I got offstage without tripping on the mic cord. Success.
So I started again with my client’s award show draft. I wrote it with both the CEO and myself in mind, sprinkled with the kind of humour I use in everyday life. They know me, and they were commissioning me.
I ended up playing on the fact that he’s no more a comedian than I am. I added a self-deprecating comparison to a famous comedian and some lighthearted but not trying-too-hard-to-be-hilarious comments, and threw in a a couple of actual jokes along with a scripted response if they fell flat. (“I was going to tell you a time travel joke but it turns out you didn’t like it. No? Not even a pity laugh?” I TOLD YOU I’M NO COMEDIAN.)
In style, if not substance, it was a lot like my arts centre speech. I edited, came back to it after a few days, edited and polished some more, and ended up happy with it.
The client was too, enough that they came back for a second year, and that should be the most important reassurance. My main takeaway, though, is that I can best tackle projects outside my comfort zone by bringing more of myself into that zone. Even if that self won’t be getting an offer to write for Jimmy Kimmel any time soon.