Reader Case Study: Building a Comedy Writing Career in the Short and Long Term
How do you balance short-term and long-term writing goals if you want to make a stable living by writing?
I got a thoughtful question recently from Henry, a reader.
It’s a bit longer: closer to a case study. But it’s a good case study, so let’s dive in…
How do you balance short-term and long-term writing goals if your long-term goal would be to earn somewhat of a stable living writing comedy, selling long-form projects?
Obviously, I’m not trying to ask “how do i become rich and famous from comedy”. I genuinely love the craft. I’m in a writing group. I love writing comedy and it’s a blast.
But at the same time, I do have goals of creating and selling longer-form projects, like comedic graphic novels and short stories/books. I have an email newsletter and am in it for the long-haul.
Just trying to find the balance between short-term goals of working on the craft and cracking into selective short humor comedy publications to build a following and long-term goals of collaborating with an illustrator on a comedic graphic novel (think Emily Clouse’s comedy cartoons and website as a whole) or creating a longer-form comedic story like Simpson’s writer John Swartzwelder’s Detective Frank Burly series. - Henry L
Thanks for the question, Henry.
You’re already doing a lot right, so let’s acknowledge that.
You’re in a writing group. Good. I’ve talked nearly ad infinitum about the importance of elevating your craft through peer critique. e.g.
You’re treating yourself like a pro. You have a writing newsletter, a personal-professional website, and you’re publishing funny pieces on Medium. Great.
Even better: you’ve identified what you specifically want in the long-run.
Write and publish comedic novels, comedic graphic novels, short stories/a short story collection, or maybe other comedy books.
Make a living doing this.
That’s more specific, and therefore much better, than just a vague sentiment like, “make a living with my writing.”
You’ve also identified some short-term goals:
Work on your craft and keep getting better.
Get humor pieces into selective humor publications.
Build an online following.
So, your question boils down to: how you do you balance those two sets of goals?
I think your goals are well laid out and thoughtful.
Here’s how I’d approach your situation.
First, I agree with you that “work on your craft and keep getting better” should always be an anchor goal, short-term and long-term. With that goal, there’s no conflict or need to balance anything. Eternal growth and evolution is a cornerstone. Keep chipping away and pushing yourself, day by day, month by month.
Second, why not concurrently work on short form humor pieces while writing a longer-form work? Lots of feasible ways to work this. Maybe you work on your book draft every Mon, Tues, Wed, and your short humor every Thur, Fri, and Sat. Sundays off. Or maybe you write 2.5 hours every morning (early), M-F only: 75 minutes for your book, then 75 minutes for your humor pieces. Weekends off. Or whatever works for your schedule.
In my experience, having a couple of different concurrent writing projects is not too much and can energize you. It can feel good to swap one project out of view and focus on something else for a few days.
Third, publishing pieces in selective comedy publications will increase your funny writing skills across the board. And it will boost your visibility and portfolio in ways that will, directly or indirectly, open up opportunities for publishing longer-form work. So, here, the short-term goal will serve the long-term goal. These should balance quite well.
My advice would be to work on publishing some top-tier humor pieces you are very proud of: perhaps at least five to ten pieces. Every 6 months or so, evaluate where you’re at and whether additional short form pieces are in the cards, or whether they’re offering diminishing returns. At a certain point, the marginal value of more short form pieces may diminish. (But still, if you’re having a lot of fun doing it, you can keep doing it, as long as it’s not detracting from creating the long-form work.)
In short, publish several top-tier pieces, check in with yourself, then make sure you have sufficient time to pour into your longer-form projects.
Fourth, publishing short form pieces in selective comedy publications (e.g. McSweeney’s) will not grow you a large audience. These pieces do not include any direct way for readers to follow you, so they’re more about improving your craft, getting a by-line, and getting the portfolio credit than they are about raw following. You may get a handful of loyal followers from such pieces, but not a thousand handfuls.
