Last month I went to the Sundance Film Festival for the first time ever because, against all odds, I had a film premiering there. The film is a documentary called Misery Loves Comedy, and it basically asks the question, “Do you have to be effed up to do stand-up, or does doing stand-up eff you up?” (Spoiler alert: yes.) I’ll talk in a moment about what it means to “write” a documentary, but first I’d like to tell you how I got the gig to begin with, and why I took it, because it speaks to one of my core values as a writer: flexibility.
Years ago, as some of you know, I wrote a book on writing comedy called The Comic Toolbox. Fewer years ago, as fewer of you know, I became something of an expert in the field of poker (well, “expert” – I wrote many books on the subject). At some point in the dim and distant past, I played poker with a guy who, as it happened, was a fan of The Comic Toolbox, and we stayed in vague touch for many, many years. Eventually he went into the business of producing documentaries, and since my ideas resonated with him, he asked me if I’d like to be part of Misery Loves Comedy.
So, first lesson: You never know what’s going to wash up on your beach. A book I wrote to clarify my own understanding of comedy, plus many books I wrote to exploit a hot market (poker) created the unforeseen opportunity to do something I’d never done before, write a documentary.
What does it mean to write a documentary? In my case, it meant writing a bunch of framing documents that moved the concept from amorphous goo into something more structured, and writing a lot of questions for the director to ask many comedians. When I said yes to the gig, though, I didn’t know the first thing about writing a documentary. I’d never done it before, didn’t know if I could do it, but that didn’t stop me, or even slow me down, because, second lesson: Never leave money lying on the table. If someone wanted me to pay me to write a documentary, I was by gum going to write a documentary, whether I knew how to do it or not.
Did I have to fake it? Somewhat, but it really wasn’t a problem. I’m long practiced at the art of representing myself as an expert at anything. Frankly, it wouldn’t occur to me not to. If I am committed to learning and growing as a writer (and I am) then I must necessarily accept every challenge that comes my way – especially ones that pay – even if they scare me. [pullquote] If I am committed to learning and growing as a writer (and I am) then I must necessarily accept every challenge that comes my way.[/pullquote] So, third lesson: Do it, even if you’re scared. Do it even if you’ve never done it before and even if you’re not sure you can do it. Don’t let fear of failure ever stop you from trying.
I’m looking over my own shoulder as I write these words and I’m thinking, “That’s easy for you to say, JV. All these wonderful opportunities just seem to come your way – wash up on your beach, as you say. What about other writers, struggling writers, who don’t have their fingers in so many comedy-writing and scriptwriting and poker pies as you?” Well, what about them? They know many things that I don’t know, right? They have many skills that I don’t have, yes? And they have a synergy of knowledge and skills that will create all sorts of opportunities just for them; opportunities unique to their experience. Which brings me to lesson four and back to lesson one: flexibility. Go off in all directions at once, you’re bound to arrive somewhere eventually.
One thing my writing life has taught me is that I never know what lies ahead. Incredible gifts have come to me – amazing opportunities to write things I’d never dreamed of writing – just because I let myself be open to them, and because I never said no. I seized every writing gig that came my way, the ones I thought I could master and the ones I was sure I would blow. I just didn’t care. Writing is writing and a gig is a gig, says the guy who once wrote 5,000 questions for Sports Jeopardy Online.
A lot of writers, I think, labor under the misapprehension that “if it’s not my passion, it’s not legit.” Though I clearly understand the difference between my passion projects and my paycheck projects, I don’t look down my nose at the latter, because I know how the paycheck projects sustain the passion ones. The paycheck projects also – always – shed new and unexpected light on how to be a writer; they make me better at my craft. Thus they they create opportunities to extend my passion in new and interesting ways.
Sometimes they bring me to Sundance.
So that’s why I say go off in all directions at once. If there’s a downside to this strategy, I haven’t found it yet. There’s one perceived downside, and that’s that the pursuit of paycheck projects will somehow distract us from the passion projects. This hasn’t been my experience. I’ve learned so much from writing things other than what I “should be writing” that I can’t see anything but benefit. Maybe I’m blind. And maybe I’m a slacker, squandering my gifts on dumb documentaries when I “should” be writing that 800-page philosophical magnum opus that places me in the pantheon. Oh, well. If it’s mean to be, it will be. Meanwhile, I’m going to keep doing what I do (lesson five): Walk down the beach, pick up everything you find, and turn it into a party hat.
What about you? How do you balance the work you do for love with the work you do for money? What strategies do you find particularly effective both in getting paycheck projects and then executing the ones that take you outside your comfort zone?