How I Write: Sarah Kessler, author of GIGGED
“At some point, I realized I should start.”
Every month, I interview an author with a new book about her or his writing process. This month, it’s Quartz editor Sarah Kessler, a former colleague of mine at Mashable and a fantastic journalist and storyteller.
She’s the kind of writer that gives me a motivating amount of professional jealousy. And her new book, Gigged: The End Of The Job And The Future Of Work, is fantastic. You can learn more about the book here, and about how Sarah writes below this photo of her writing desk:
What’s your process for a big writing project like GIGGED?
SK: When I started working on GIGGED, I knew I wanted to tell the story of the “gig economy” through the perspectives of people who were actually working in it. I also wanted to explain how this Silicon Valley idea fit into wider labor trends (spoiler alert: companies have been outsourcing work to non-employees whenever possible for a very long time) and what it meant for our future.
I wanted to do all this in a narrative-driven way that would be pleasant to read, rather than in a business book full of bullet points.
I had no plan.
But because I had a full-time job as a reporter, I was already somewhat immersed in this world. When I met someone interesting who worked in the gig economy, I would ask them if we could talk regularly. I started nine relationships like that, and five of them ended up in the book. At the same time, I was reading everything I could about the history of this kind of work, and reporting day-to-day on gig economy businesses and the conversations around them.
At some point, I realized I should start. I used post-it notes to make an outline on the floor of my bedroom. I moved the outline to the wall. I wrote a terrible first draft.
Then, I waited about six months. This ended up being great because it gave me the space I needed in order to see that the first draft was terrible. I rewrote it. I rewrote it again.
What’s the worst gig you ever had?
SK: Early on in the gig economy, for a magazine story, I signed up for a bunch of apps like TaskRabbit and Fiverr to see if I could make the minimum wage. Somehow, I ended up in a proposal flash mob. At the rehearsal, I learned that everyone else was a professional dancer who knew what it meant when someone yelled “sashay!”
The final performance involved stuffed penguins and 10-degree weather. If you were to see a video (which if I can do anything to prevent it, you never will!!), you would spot my unique interpretation of the proper dance moves instantly. I think I made $20 for two hours of rehearsals, plus the performance (which required two hours of travel time and 30 minutes of waiting outside).
What rituals, if any, do you have as a writer?
SK: When I was working on the second and third draft of GIGGED, I would come home from work, make dinner, and then write for a couple of hours before bed. I always made a cup of tea before I started writing, which was a helpful routine that made it easier to transition into writing mode.
What’s your writing toolkit?
SK: I used a software program called Ulysses to write GIGGED. It allows you to write in “sheets” that you can drag and drop to rearrange, which is helpful when you’re thinking in chapters rather than about one short piece.
Where do you go for inspiration?
SK: Anywhere there is great writing. Sometimes that’s reading a perfect magazine story. Sometimes it’s taking a break from facts and reading fiction. Also, a walk will always help.
What’s your favorite thing you’ve ever written in your life?
SK: This is such a hard question. I’m sure that I have some amazing poetry tucked away in my high school journals, but I’m going to keep that idea alive by never going back to read it. One piece I loved was about my time hanging out with YouTubers in LA. Another was about how the sharing economy is dead. And of course, that time I tried to make it in the gig economy.
What’s the first book you remember loving?
SK: The Chosen, by Chaim Potok. A novel about teenage boys in Brooklyn and their evolving relationships with Judaism was probably an odd choice for a fifth-grade girl attending Catholic school in rural Wisconsin, but I think that was part of the appeal — it described a world so different from my own at a time in my childhood when I was just beginning to realize that such worlds existed.
What’s your best piece of advice for writers?
SK: Be willing to shift mindsets. Writing, for me, is about letting go and being confident in my instincts. Self-editing, which is a requirement for good writing, requires almost the opposite state of mind. It’s about doubting every word I’ve written and challenging my own ideas.
What do you want written on your tombstone?
SK: “TKTK”
Shane Snow is author of Dream Teams and other books. Get his newsletter about thinking differently, The Snow Report, here.
