scorecardI've made thousands of dollars writing trivia questions as a side gig. It helps me pay my rent and makes socializing so much easier.
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I've made thousands of dollars writing trivia questions as a side gig. It helps me pay my rent and makes socializing so much easier.

Noah Sheidlower   

I've made thousands of dollars writing trivia questions as a side gig. It helps me pay my rent and makes socializing so much easier.
Careers3 min read
Noah Sheidlower writes and edits trivia questions as a lucrative side gig.    Noah Sheidlower
  • Noah Sheidlower has made thousands writing and editing trivia questions for school competitions.
  • His side gig has helped him improve as a reporter and connect with people from varying backgrounds.

A few weeks ago, I was at bar trivia struggling through a music round when one of my friends asked the table: "Who actually writes these questions?"

"Me!" I shouted, followed by, "sort of."

My friends were shocked. "I thought AI wrote some of these, honestly," one said. To be fair, I don't often write the one-liner, pub-style trivia questions that trivia enthusiasts and beer lovers alike play every Tuesday night. In fact, most of the people who compete on my questions aren't legally allowed to drink.

Outside of journalism, I write and edit trivia questions for various high-school and college competitions as a side gig. I've made thousands of dollars writing and editing thousands of questions in the last year, and I'm still going strong.

My questions are written for everyone from elementary schoolers to graduate students, meaning one day I'm writing 75-word questions on the most basic of history facts, and another I'm spending half an hour on a 250-word question about obscure classical music. For many of them, the answers are much, much harder than what you would ever see on Jeopardy!

Learning more about the world through writing questions helps me pay my bills, do my job as an economy reporter better, and ultimately connect with people from all sorts of backgrounds — a particularly useful perk as a recent graduate trying to make new friends. And they've helped many in the quiz bowl community want to learn more and become more inquisitive about the world.

The art of the trivia question

Getting these gigs was years in the making. I started playing for my high-school quiz bowl team as a freshman, learning the ins and outs of which artists were asked about, what authors were worth studying, and what historical events were fair game. I started as a 14-year-old not knowing the order of the US presidents, and by the following year, I was answering questions about each president's specific policies.

After attending national competitions in high school, I joined the Columbia University quiz bowl team, winning a national competition in 2021. While in college, though, I realized I enjoyed writing and editing questions even more than competing, and I successfully applied to a few companies looking for writers.

Some weeks, I was writing as many as 100 "pyramidal" questions — meaning the more obscure information comes first, followed by increasingly more well-known clues — on everything from Asian geography to British poets to jazz standards. It wasn't until I graduated college that I saw more opportunities open up through word of mouth and online applications, especially now that I could write collegiate questions, many of which are notoriously difficult.

With practice and lots of reading — at one point, a book a week — I kept improving. Sometimes my questions fell flat or were written in the wrong order, though I became more confident in my craft.

I use "craft" intentionally. Players only want to hear the same Jane Austen or Frederick the Great clues so many times. Part of what makes quiz bowl writing so fun — and what keeps me going even when it feels like I've asked about everything I could think of — is figuring out a fresh and interesting way to ask about a topic.

The joy I get when a player shouts "That's a cool clue" for one of my questions is often unmatched.

Using trivia to inform my reporting

Sometimes as I learn new facts through writing questions, I notice that hidden within them are stories. For example, after researching historical questions on the Hmong people over the last year or two, I realized that many new Hmong businesses have been opening across the country this year, inspiring an enterprise project I completed in July.

My knowledge of the history of the nation's Chinatowns and Chinese American culture from writing questions inspired a lengthy story on how luxury development has in many ways harmed the fabrics of Chinese enclaves nationwide. And my studies of composers and their works inspired a story on how Black composers who have been mostly forgotten by orchestras have recently had their works played by major ensembles.

In the last few weeks, I've found myself talking to friends I recently met on everything from US industrial labor history to Singaporean culture to Australian politics.

It's also made socializing easier, since I'm usually able to chime in on random topics that people are passionate about.

And who knows, maybe the next trivia question I write to make some extra change could be my next big story? (No spoilers.)