What is “Taking a Chance?” Lessons from a Day on “Jeopardy!”

As you may have seen on our social media, our very own Katie O’Shea appeared on Jeopardy! earlier this summer. In addition to being proud of Katie, we have enjoyed getting some behind-the-scenes insight of how one of the world’s most famous game shows operates. We asked Katie to share her experience here.

If you’ve ever watched the show Jeopardy!, you know that there’s the classic music, the acerbic host, the three players, and, of course, the answers that are all in the form of questions. (You probably also know all of that if you’ve gone to middle school in America, where some teacher along the way inevitably will use the Jeopardy! format as a means to engage the tweens.)

What you probably wouldn’t be able to guess is that the studio is smaller than it looks on TV, that Alex Trebek is charming and gracious in person, and that the buzzer is much trickier to handle than you would expect.

In March of this year, I had the opportunity to make all those realizations myself, when I found myself standing on the stage in the Jeopardy! studio, buzzer in hand.

My Jeopardy! story begins back in January 2017, when I signed up to take the online test for potential contestants. I had just recently come back from visiting my family for the holidays, where we had, as we always do, watched a lot of Jeopardy! (That’s one of the main perks of having access to cable TV.) I just thought the test would be fun to try. The tests are only offered once or twice a year, so I knew it would be a little while before the next one. I signed up, then mostly forgot about it.

A few months later, in May, I got a reminder about the upcoming test. On June 1, I took the test. I felt relatively confident about my answers, but had no real expectations of it going anywhere.

That’s why when, in mid-July, I received an invitation to audition, I was more than a little shocked. The audition was held one month later in Chicago, in a conference room of a Michigan Avenue hotel. There was an in-person test to prove that we hadn’t cheated on our prior online test, then each of the 25 or so people in the room took turns in simulated gameplay, which was recorded, as they said, “in case one of you ends up being the next Ken Jennings and the local news wants to play a clip about how it all started.” In the course of that, people introduced themselves, and I started to see just how wide a range of people were fans of the show. There were teachers from Wisconsin, dads from Minnesota, retirees from the suburbs, and even a Canadian. At the end of that session, they told us that we would either hear from them sometime in the next 18 months or not at all — in which case, we were welcome to retake the online test at that point.

Within a few months, I had largely forgotten about the whole thing. When I had found out about the audition, I had made flashcards with the names and dates of the U.S. presidents and even perused them a little, but with the odds of getting on the show seemingly slim, it didn’t feel necessary to study.

Fast forward to March 2019: a voicemail message from a Culver City number pops up on my phone. I listen, and it’s someone named Glenn from Jeopardy! who says he just needs to review a few details from my application to make sure they’re still current.

After googling his name to make sure it’s not a scam of some kind, I call back and Glenn asks me the various questions I had answered on my form in August 2017. I confirm the answers to all the questions, then he says, “Okay, great! We’d like you to be on Jeopardy! in two weeks.” I’m stunned. I’m sitting in the 3Points conference room while talking on the phone, and at this point, I have to look through the glass to make sure it’s still real life. He walks me through all the details I need to know and tells me about the different paperwork I’ll need to submit before I arrive. Even though it’s a talk I’m sure he’s given a million times, I’m struck by how personal the conversation feels.

After I get off the phone, I walk back toward the desk area, where just Sam is sitting. “Sam, this is crazy, but… I’m going to be on Jeopardy!” As I fill Sam in about what just happened, I realize I’m shaking and starting to feel a little giddy.

This feeling is quickly replaced by another: the feeling that I really need to study. I begin listing the various topics that I think I need to focus on. The next few days, Sam quizzes me at lunch each day about world capitals, U.S. presidents, and notable bodies of water. Maddie and Mike jump in to ask me general knowledge questions. I end up borrowing an almanac from the library (though, slightly disappointingly, it was a 2016 edition, not 2019 — who knows what new facts I might have missed out on?).

I complete the paperwork, which includes a list of potential fun facts to talk about during the part of the show where the contestants are interviewed (completing that part is much harder than it sounds — and it can lead to the minor existential crisis of realizing you are less interesting than you previously imagined). I pack my bags with the clothing I’m planning to wear on the show, as well as the mandated changes of clothing to wear in case I make it past one show, and of course the flashcards and almanac.

My family and I spend a couple days in LA before the filming day. In the mornings, they go sightseeing while I stay in the hotel studying geography and betting strategy (the latter is not in the almanac, but is widely discussed online).

The day finally arrives, and I find myself waiting at the hotel entrance for the contestant shuttle. It’s unmarked, so I nervously ask someone else if they’re going to Jeopardy! They are, which makes sense — where else would a shuttle of nervous-looking people dressed in business casual on a Saturday morning at 7 a.m. be going?

On the shuttle, someone breaks the silence by asking where everyone is from. Everyone goes around and says where they’re from. A little more silence, then someone asks what everyone’s professions are. Several, it turns out, are teachers. Everyone seems friendly, though a little anxious.

When we arrive at the studio, Maggie from the Jeopardy! team greets us. When she says to the quiet teacher from Minnesota, “Hey, champ!” I suddenly realize that he’s a returning champion. Suddenly, I feel more nervous — it never occurred to me that successful, nerdy interlopers would blend in so well with the hopefuls.

We get ushered through some more paperwork, makeup, and an informational talk about how the day will go and everything else we need to know from Maggie, who deftly puts the room at ease. I drink several of the mini water bottles in the green room. Then we go to the set to film promotional clips and rehearse answering questions. (Note: if you are ever on the show or at a taping, wear a sweater — it is freezing in there.) Jimmy from the Clue Crew plays Alex as we practice buzzing in to answer questions. We learn that it is difficult to get the timing right — buzz in too early and you get locked out from buzzing in again on that question for a quarter-second.

Soon the filming begins. There are five episodes taped on each filming day. (There are usually two filming days per week.) The two people chosen to face the returning champ for each episode are chosen randomly before each episode. Everyone else waits and watches from the audience, just across the aisle from their anxious friends and family. I have no photographic proof of this, as you are not allowed to take photos in the studio. (I can confirm that my mother was caught attempting to take a photo anyway.)

I watch the first three games, feeling more confident about my coming game as I get questions right — and less confident when I have no idea. The returning champ, Sam (the teacher from Minnesota), wins the first two games of the day, but loses the third. After he leaves, the remaining contestants assemble for lunch in the green room. Someone jokingly asks what everyone’s weakest categories are — but it’s all in good fun, and everyone laughs.

We return to the studio, and now I know for certain what I had suspected might happen — I’ll be on the last game of the day. I sit in the audience with just two other people. A local retired doctor who was an alternate that day is told to sit between Jason, who will be one of my opponents, and me, to prevent…collusion, I guess? Or maybe trash-talking?

Then it’s my turn, and honestly, it’s a blur. I answer questions quickly and sometimes get them wrong. Sometimes I struggle to get the buzzer timing right. I go into and pull out of negative scores a couple times.

Spoiler: I didn’t win.

I wasn’t really disappointed about not winning or not getting more money. But I was worried that my friends, family, and more distant acquaintances, who had already sent so many messages of support upon learning that I would be on Jeopardy! would be disappointed. As the air date for the episode approached and others would tell me that they were excited to watch the episode, I would try to remain sphinxlike and say, “thank you,” and try not to reveal in my reactions anything about the way the game had gone. I fought the impulse to try to temper their expectations, knowing that it would violate the NDA I signed. (I wasn’t allowed to say anything about the results of my episode, individual questions or categories, who I played against, etc. — it was a strange four months.)

Yet, on the air date, surrounded by friends and 3Points clients current and former, I was surprised by how wrong I had been to be worried. No one seemed to mind that I didn’t win. No one cared that I had invited them to leave work that afternoon to watch me not win. (Or, if they did care, I guess my friends are very thoughtful and/or very talented at deception, because they hid it well.)

And when I rewatched, I realized that I couldn’t have done it any other way. Yes, I buzzed in and sometimes gave the wrong answer to questions I wasn’t sure about, but if I’d stayed silent and hadn’t tried, I would have felt worse about the whole thing. Maybe it’s not the smartest way to play Jeopardy!, but it was the only way that felt right to me.

I recently realized that I was essentially doing what the head of my high school and 9th grade English teacher had always urged us to do: “dare to fail gloriously.” Yes, I didn’t “win,” but I put in my all and, in that way, I won.

I may have failed, but I think I did so gloriously. I walked away with the memory of a truly incredible experience. I had met kind, intelligent people (and one of these people, my opponent Jason, went on to win another 18 games). I had seen photos of Alex Trebek standing halfway in the floor of his home in work clothing, remodeling his wife’s bathroom. I had actually met Alex Trebek, period. I gained a fun fact about myself that I can use in icebreaker activities for the rest of my life. And then I got to have a party a few months later with many of those who are near and dear to me.

Plus, I did at least end up winning $1,000 from the game, so if you want to chat more about it over a beer sometime, drinks are on me.

PR & Communications for Fintech & Chicago Tech. www.3ptscomm.com