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Amy Schneider has always been smart, but she hasn’t always felt like it. It wasn’t until her 30s that it became clear just how many ways of thinking exist. With this new perspective, she saw her identity and abilities in a new light and, famously, went on to shatter records on the quiz show Jeopardy!. Amy and Stephanie talk about how the more you know, the more you realize you don’t know, the fateful timing of her success, and how she now realizes it couldn’t have happened any other way.

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Transcript

SPEAKERS

Amy Schneider, Stephanie Wittels Wachs

Amy Schneider  00:00

I had been okay with going on TV as a trans person, because I just thought I was going to be on Jeopardy for a game or two, the only things I was thinking about were like, would I feel dysphoric watching myself and seeing myself on TV like that was the only downside I was worried about. And then realizing that I was going to be, you know, in in headlines and things like that, and, you know, was like going to become a target for people. It was frightening, to be honest.

Stephanie Wittels Wachs  00:33

Some big dreams take forever to realize, years, decades even and lots can change between now and forever. So imagine your big dream finally becomes a reality. And it is nothing like you expected it to be. But you have to take the leap, whether you feel ready or not. Some people well, they leap.

Amy Schneider  01:01

This is the only chance I was ever going to have to make you know, $150,000 in a day. And I wasn’t about to let any you know, sort of fears of like, you know, Twitter trolls like distract me from that opportunity.

Stephanie Wittels Wachs  01:26

This is Last Day, a show about the moments that change us today, a story of preparing your entire life for one moment, and it’s still catching you by surprise. What happens when you choose to take that headfirst dive into the unknown?

Stephanie Wittels Wachs  01:51

Amy Schneider occupies a coveted role in society. She is known for being smart, really smart, shattering records on the quiz show Jeopardy smart. But she’s not just smart, she’s curious and she always has been. In fact, the tagline of her new memoir reads the joys and rewards of a curious life. For as long as she can remember, Amy was this way, she aced tests and spelling bees, she knew a lot about culture pop and otherwise, she was also incredibly well mannered. And this well behaved star student persona all started in a small Catholic community in Dayton, Ohio.

Amy Schneider  02:33

It was really kind of a mixed bag, and like politically, like it was very, I would say, progressive in terms of sort of racial equality in terms of economic point of view. But when it came to the teachings of Mother Church was very much Orthodox and by the book and and rule bound, and that sentence, so not progressive at all, in terms of sexuality, for example. So that was definitely one of the things that shaped me. I think the other aspect of my upbringing that shaped me was our parents that were intellectual. You know, my mom was a math professor. My dad was a computer programmer, he worked at university. And so they were very much about learning and curiosity and discussing intellectual things, the life of the mind, as my mom called it.

Stephanie Wittels Wachs  03:27

I mean, I love the direct A to B like discussing electoral things to a Jeopardy champion.

Amy Schneider  03:34

Indeed, no, it was very preordained by, you know, I’ve watched the show my whole life, and it was always exactly, you know, not just education and intellectual stuff, but like that specific kind of just sort of being well read and familiar with the canon and knowing the basics about everything, as opposed to necessarily being about grades and getting into the right college and all that sort of thing.

Stephanie Wittels Wachs  04:01

Knowledge, like actual pursuit of knowledge.

Amy Schneider  04:04

Right, exactly, you know, for my mom in particular was something she had been raised with, because she was raised in a very wealthy Protestant suburb basically, and was always very conscious of being looked down on as Catholic and that Catholics were unintellectual and suspicious. And so she’d been raised to be very like, no, we can talk about classical music and Shakespeare just as well as anybody.

Stephanie Wittels Wachs  04:29

I love that, which classes are you sort of connecting with in school and outside, like, what are your interests in school and extracurricular really?

Amy Schneider  04:38

Yeah, I think that in school, math certainly was one that that came very easily to me. I was sort of a year ahead for almost my entire academic career. I was taking one year ahead and maths. And it’s one of these things where I would be a terrible math teacher. You know, my mom was a maths teacher, but I wouldn’t be able do it because like, people would ask me for help, and I’d say, will you do this? And they’d be like, I don’t get it, it’d be like, well, then I’m out, I don’t know, because I got it the first time. and I don’t know how I did it. It just was obvious to me.

Stephanie Wittels Wachs  05:12

As you go into high school, I’m so curious to dig in here. It seems like your understanding of being smart, I started to kind of shift that things started to become more challenging, different difficult, can you talk about that time?

Amy Schneider  05:27

Yeah, I think that, you know, in high school, and I think as I have found sort of, you know, community, academic performance in and of itself, I found, you know, it was great for getting approval from grownups, but in high school, that becomes less important, and you want approval from your peers, and I found that, you know, my academic performance was at times somewhat counterproductive towards that, that there was a certain amount of resentment, I guess, I would say, which I, you know, I don’t want to overstate it, but things came easy to me in terms of getting grades and, you know, my SATs scores and everything like that and the people around me who are working harder and not getting the same results, you know, weren’t thrilled for me, I have to say, and so it became something that I became almost more defensive about than the thing you know, the thing that had previously been kind of my whole identity became something I was starting to try to downplay more.

Stephanie Wittels Wachs  06:28

And there was also some struggling with undiagnosed A D D, and how is that kind of rearing its head or not in school and out?

Amy Schneider  06:38

Yeah, I mean, I think that you know, A D D at the time wasn’t something that I considered was like a thing for me because add meant that you were like, misbehaving and couldn’t sit still, although, I mean, in retrospect, I couldn’t sit still I remember like being asked, like, what do you have to go to the bathroom or something? Like, why are you so like fidgety in your chair? And I’m like, What? No, I, you know, I don’t even realize that I’m fidgeting. So here, I am attempting to downplay the sort of academic success I’m having while at the same time, A D D makes it really hard for me to do homework and complete assignments and things like that, which all fit together very neatly. So yeah, it was something where whatever it is about my brain enabled me to skate by, and then the A D D, helped me, I don’t know what the opposite of skating by is, but help hold me back in a way that I wanted to be held back at the time.

Stephanie Wittels Wachs  07:34

So as Amy gets older, her notable brain power is taking up less of the spotlight, which is somewhat by choice, and somewhat for reasons out of her control. She starts finding connection with her peers through other outlets, like theater, which, as you might already know, I deeply relate to.

Amy Schneider  07:55

You know, outside of school, the main thing was theater. I got into that when I was like 11 and.

Stephanie Wittels Wachs  08:01

I was four, I was, yes, I get.

Amy Schneider  08:05

Oh, yeah and once once I found that I was like, you know, there was no looking back for me I loved, loved loved it. You know, I think from the outside, I think when people think theater kid, they just think of the sort of diva theater kid that wants to be the star and all that sort of thing, which is definitely one of the types of theater kids. But there’s a bunch of other types too. You know, I always say people are in theater, either because they want to be seen or because they want to be hidden, they want to disappear into some other role or even, you know, the theater Tech Kids, which is a whole nother group, and it takes all of you to put on the show and every one of you can ruin it for everybody else. You’re all dependent on each other, you’re all exposed in this, you know, sort of vulnerable way. And when it works, there’s nothing like it.

Stephanie Wittels Wachs  08:57

Even with a thriving theatre life, there’s still something about academics, that gives me comfort, for one, it’s something that adults, including her parents, pretty much all agree as good, a high grade, something she can show to the grown ups in her life and know they’ll be impressed. And as it turns out, this black and white nature of school, especially math, is a refuge for young Amy in other ways.

Amy Schneider  09:24

You know, even beyond just my parental praise, it was you know, grades and standardized tests and spelling bees, they were unambiguous. You got a number and the number of said that I had done the best and that, you know, I had achieved as well as I could and I didn’t have to feel any doubt about it. There was no ambiguity about it. I think that for whatever reason, and it’s one of the many things that I kind of like read back my gender confusion on too, but I found so much of what was expected of me to be unspoken and conveyed Using like, unwritten rules that you’re maybe supposed to be following, and maybe not. But when it came to a test, there was no confusion about what the thing to do was you get all the answers right, and you get the best grade and you can feel good about that.

Stephanie Wittels Wachs  10:17

But Amy didn’t know at the time and wouldn’t know for years is that she’s trans. As a kid, she’d get enrolled in things like Boy Scouts and hate every last second of it. She was confused about what she could and couldn’t do, how to gain social approval, why it mattered so much, you know, all those rigid unwritten rules that young people are expected to follow, but are never actually taught. Growing up in the Midwest in the 80s isn’t exactly the best environment for someone trying to make sense of themselves, especially when it comes to things like gender, and neurodiversity. It isn’t until years later, decades, actually, that Amy finally gets a chance to look at her brain, her body and her identity with a gentler, more curious gaze. Much to her surprise, the absence of black and white grading and tests actually helps, and perhaps less surprisingly, it all starts with a move to California. When did you move to the Bay Area?

Amy Schneider  11:24

2009, so the year I turned 30.

Stephanie Wittels Wachs  11:27

Oh, wow, so into a new decade into a new state and to a completely new community? Can you remember those first like few months, was it wonderful was a terrifying what was?

Amy Schneider  11:40

It was, you know, it was it was all of these things. It was, you know, I had not really ever envisioned moving out of Ohio, it was, you know, I just believed that I was stuck with what I had been given, which was, you know, being a boy that was Catholic in Ohio and all of this sort of thing. And I hadn’t let myself think about another way of doing things. But my now ex wife, Kelly wanted to move out here, and she was a powerful personality and brought me along in her wake. And I’m extremely grateful for it. I mean, really moving to the Bay Area was really where I truly got comfortable with my sort of intellectual prowess or whatever. Again, after high school, people wanted to talk about ideas and you know, discuss interesting, abstruse topics and all of that sort of thing in a way that I immediately like felt at home in.

Stephanie Wittels Wachs  12:37

And if you’re confused about your gender expression, or identity as a young person, it’s interesting as you become an adult, learning for the sake of learning and gathering knowledge for the sake of enjoyment, and then figuring out that identity and it not being this confusing morass, but this sort of thing that you are claiming, right?

Amy Schneider  13:00

Yeah, yeah, definitely. I think that the thing about learning is that, you know, especially once I was doing it for myself, and not for passing a test, in order to learn, you have to let go of things that you’ve learned that we’re incorrect, you know, like, the way that history was taught in the 80s like American history and things about like reconstruction and things like that, and then growing up and exploring it for yourself, and and, you know, learning what wasn’t true about that, and what was misleading and what things I I believed about the history of our country and, and race relations and things like that, that weren’t actually true. You know, it took me a long time to move from doing that in the intellectual sphere to doing that about myself. But I was able to, you know, take in new information about what trans people were, and you know, what sexuality is all of these things. Because I had that sort of mental pathway built up that skill built up of being able to realize I had been wrong and let it go. So moving to the Bay Area, I was definitely exposed to a much different view of human sexuality and gender expression than I had had on Ohio.

Stephanie Wittels Wachs  14:29

We are back and it’s now 2016. Amy has been living in Northern California for seven years, and it’s around this time that she begins her gender transition. She’s coming into the truest version of herself, and it’s a result of being steeped in a community that honors curiosity, and different ways of thinking and expression. Learning is becoming fun again. And for Amy, that means giving more attention to a long standing passion of hers. It sounds like you always wanted to be on Jeopardy. You said you watched it as a kid. At what point were you like, I want that.

Amy Schneider  15:10

Um, I mean, you know, more or less as long as I could remember. I mean, it was pretty much a nightly thing with our family. We always watched it, our television watching was fairly closely monitored and circumscribed. But it was something that I could watch with my parents that they enjoyed it, you know, and it made me feel like a grown up to be watching it with them. And it was, you know, again, the sort of thing that came pretty naturally to me it fit exactly with this sort of skill set that my brain was wired for. You know, it’s, it’s a standardized test every night.

Stephanie Wittels Wachs  15:46

It’s your love language. And to be clear, this love language sticks around, even once Amy starts to, for lack of a better phrase, expand her mind in California. Before and after her move to the West Coast. Amy is thinking about Jeopardy. She’d started auditioning for the show a few years prior to the move. And she feels encouraged to keep trying when she meets all those like minded thinkers in the Bay Area. She tries out for the show every year for 15 years. And she occasionally gets called up to do in person auditions. For people who like to take time tests and then be put on a waitlist for 18 months that may or may not result in having to demonstrate their smarts on broadcast television. It is a fun process. Amy treats the tests and occasional callbacks, like a hobby, which she especially enjoys as an escape from her lackluster career as a computer engineer. But by 2017, Amy has transitioned. So even though Jeopardy has long been a positive presence in her life, some new concerns start to creep onto her radar.

Amy Schneider  16:56

Yeah, I mean, I started trying out well before I transitioned probably a decade and so for all that time, you know, the fear of being in the public eye was not a problem. That’s where my theater background had come into play that like I knew I could go on stage not have stage fright, and be fine with people seeing me like that. But then I transitioned, and in that early period of transition, I didn’t want anybody to see me, I all that theater kid confidence was lost. Because I felt so you know, I felt so self conscious, so aware of how people were perceiving me, were they perceiving me as a woman, were they perceiving me as a man and address as I sort of always put it in my mind? You know, I said something on, there’s like, Trans Day of visibility and I was always like, I don’t want no, that sounds awful. I don’t want Trans Day of visibility, I’m tired of being visible. And so, you know, for a couple of years there, I put the Jeopardy thing on pause, because I could no longer, you know, imagine being on TV, and all the sort of psychological stresses that would go with that. But transition is you know, that that stage is temporary, it feels like you’re always going to feel that way it feels like you’re never going to get past it. And you’re never going to be comfortable that you’re never going to stop wondering how people are perceiving you. But it turns out that you do get past that, and you do get to the point of this is who I am. Most people seem to be fine with it, those that aren’t are wrong, and I just don’t care anymore. You know, and it wasn’t as simple as that. And certainly when I did start, go back into the process of auditioning for Jeopardy, there was still a lot of fear and anxiety there. But it was outweighed by I just had always wanted to be on Jeopardy, and I was not going to be denied anymore.

Stephanie Wittels Wachs  18:56

And denied she wasn’t by 2019 Amy is auditioning for Jeopardy again. And by the fall of 2020, she gets that call that she has been waiting for her entire life. They want her on the show. And just like that this hobby has officially left happy territory.

Amy Schneider  19:17

You know, there was years and years where it was sort of like a background process in my mind was thinking about Jeopardy going through old Jeopardy games on the J archive.com on my phone when I’m commuting and things like that. You know, it’s not something that was ever I was like, you know, cramming for that I was like putting a huge amount of effort to but it was just a little bit all the time and fun and like low stakes. It wasn’t anything that you know, I wanted to be on the show, but I knew it was largely out of my control and it was just something that was just kind of fun and you know nice. And then yeah, yeah. And however while I was going to do it wasn’t going to be this like low stakes idle dream anymore.

Stephanie Wittels Wachs  20:00

The country is in the throes of COVID. So things inevitably get delayed and rescheduled. But by September 2021, she’s finally got her appearance booked. She, Amy Schneider is about to be part of the competition she spent her life dreaming of and preparing for when you get this call, and it’s time like you’re like, okay, it’s happening, it’s happening. Like that is so rare that you have a dream, and then you get to do it. You get your dream. When you get the call, like, is that registering? Are you like, holy shit, it’s happening?

Amy Schneider  20:41

Yeah, I mean, I was, I mean, again, this sort of weird thing where with that year passing, like, I knew over that whole year that I was going to be on the show. So I kind of went through that whole Oh, my God, it really happened. Like it’s finally happening. And then a year of like, Wait, is it happening? Like, I already told everybody I was going to be on Jeopardy? Like, did they think I was lying? So you know, there was that aspect of it. But then yeah, once it was those, the last, you know, week or two, before the actual real taping, it became really scary. All of a sudden, you know, because again, it was no longer this idle fantasy, this is going to be by Jeopardy experience, and most likely, that will be it, like no matter how you do, like most people who are on Jeopardy, don’t win or win one or two games. And like, that’s the end of it permanently. And so I had to kind of work through that fear and that sort of pressure. And I did feel like if I had, you know, put these decades of work into it, and then went on and had my 30 minutes on stage and lost. And that was it, that I would feel like a failure. And that was really freaking me out, and I had to get past that, in order to have a chance to win, like if I could feel how panicked I was going to be if things started going wrong. And that would become a self fulfilling prophecy. So I had to really spend a while sitting with the idea of, yeah, probably I’m gonna lose. And that will be okay. That will be fine, my dream has been to be on the show, I’m getting to live my dream, one way or the other. This is the dream, and it’s going to happen, and it’s going to be a great time. And I’m going to do my best and a lot of the rest of it is out of my control. And that’s okay.

Stephanie Wittels Wachs  22:34

So do you feel like Okay, I’m ready to be on Jeopardy. In terms of my acquired knowledge, like I feel prepared. Do you feel prepared to go on the show?

Amy Schneider  22:44

Yeah, basically, I think that, you know, I picked up the intensity a bit in the last week or two before the taping, of course, but at the same time, I mean, the one thing I didn’t like really pressure myself with was that I’ve my feeling was, the odds are minuscule that, you know, something that I like studied in the last week before the taping, is going to make the difference. Like at this point, I know what I know. I’ve watched the show my whole life, I know that I am, I’m perfectly capable of winning a game or two. I’m perfectly competent at this. I didn’t know how good but I knew I was fine. And so I wasn’t going to pressure myself about that, I was just going to, you know, that part I could trust myself on that I knew plenty of answers and it was either going to be enough or it wasn’t. But that part was going to be okay.

Stephanie Wittels Wachs  23:35

I’m so curious to know what you were feeling during those first few games, especially with what you’re telling me now that you expected you had prepared yourself to fail, you would prepare herself to to not win and win and win and win right? You were like sort of protecting your, your heart and all of that and so as you the first few games, you’re winning, you’re getting another home, you’re getting on another game.

Amy Schneider24:04

An alternative to MTV for the more mature viewer. It launched on New Year’s Day with Marvin Gaye singing the national anthem. Amy, what is the H one? Yes. And you’re on the board?

Stephanie Wittels Wachs  24:15

How are you feeling? What how are you squaring that now? What’s that conversation with yourself?

Amy Schneider  24:20

Yeah, definitely. Well, I mean, you know, the first game I played, turned out to be in retrospect, the hardest competitor like Andrew He who I defeated my first game is one of the best Jeopardy players ever. And we ran into each other early in his run and I was quite frankly lucky to beat him in that game. It came down to Final Jeopardy and he missed a question that he will say he could have gotten.

Speaker 3 24:46

Andrew He five day returning champion. What did you write down little headshake Ellis Island, you’re going to drop down 12,401 which means Amy Schneider with $31,600 you are new Jeopardy champion.

Amy Schneider  25:03

So that was an amazing feeling was like great, I won, it was so close, I got lucky at the end, but I did it. Now everything from here on out is gravy, like we’ll see how this goes, you know, blah, blah, blah, then I keep going. And the next few games, I’m not just winning, but they’re not that hard like it. They’re not that, you know not to be dismissive of anybody I played against, but I’m, you know, kind of comfortably in control of the games for the most part and, you know, and because they take five games in a day and so, as soon as you finish a game, you go to the greenroom, you change outfits, you come back, the next game starts, and there’s not really time to think about it. You know, the first day, I won three games, because I started in the third game of the day, the next day, I’ve won five more, that’s eight wins, that’s already like fairly high on the all time list. And that all of a sudden, it was something much, much more than that. And that was not something I had prepared for.

26:03

Internet International Friendship is the Final Jeopardy category today. Contestants, here’s your clue. The organization, these International was founded in 1956. Their partner states in Germany, and view Izumi lay in France. Amy Schneider, did you get […] cities? You did. And you’re going to add? Wow, another 13,000 38,000 today, your 10 day total is now $380,200. You’re in double digits. You’re a 10 day Jeopardy champion, congratulations.

Stephanie Wittels Wachs  26:49

A 10 Day Jeopardy champion, Amy has not only made it to the Jeopardy stage, she is sweeping the competition. By a dozen or so games in she realizes she’s got a hold on this game, then she’s had 20 consecutive wins, then 30 a huge turn of events for someone who had so strategically prepared herself to lose.

Amy Schneider  27:12

It still doesn’t feel real. Exactly. You know, I mean, it’s something that as what was happening, I was like, this is the sort of dream that I laughed at myself for having like my big focus throughout the streak was keep myself in the same mental state that I was in game one and keep everything the same keep my routine the same. Stay afraid of losing and keep telling myself, this was my only chance this you know, they’re coming for me like this is this is the only chance I have to win this game. And this could be the one I lose. But after telling myself that for 30 games in a row, and it not happening. I could feel my brain not believing me in the same way. And just I could feel myself just sort of taking it for granted that I was going to win. And then and I fought against that. But I could I could tell that there was a slight bit of edge that I was losing.

Stephanie Wittels Wachs  28:04

How could you not? That’s so interesting, like your brain all now is being becoming acclimated to winning, and you can’t talk yourself out of what your brain knows.

Amy Schneider  28:15

Yeah, yeah, no, for sure. I mean, Jeopardy is such a weird thing in that way, because it’s for the most part, you play until you lose and that’s it. You know, it’s not like any other you know, sport, you train your whole life to get there and you lose your first game, okay, well, you lost your first game. That’s learning experience. You come back tomorrow and try again. And Jeopardy is not like that. You don’t get to learn anything from losing. Because when you lose, you’re done. It’s very like that.

Stephanie Wittels Wachs  28:43

Well, and as a fellow theater kid, I don’t I don’t know, sports, when you’re talking about like the mindset of winning and losing. It’s so athletic, it’s so like, like, how did you know how to I don’t even know if I would know how to do the Sports Talk?

Amy Schneider  28:59

Well, I mean, I think that’s, yeah, well, I mean, I’ve been a sports fan my whole life. And I do think that that is something that was helpful that I was able to, you know, I’ve been a Golden State Warriors fan since I moved out here. And, you know, I was able to be like, I see Steph Curry going out there and being extremely confident and just trusting himself and trusting that he is that good. He deserves to be there, he’s not having imposter syndrome, because if he did, he would be you know, he wouldn’t be able to do what he does. And so be able to be like, yeah, Steph never has two bad games in a row. You know, and I won’t either, like, I’m gonna come back from this yeah.

Stephanie Wittels Wachs  29:40

After winning 40 games in a row, Amy loses. She can’t come up with the response to this high stakes final clue. The only nation in the world whose name in English ends in an H. It’s Bangladesh, by the way, which I certainly didn’t know. In the end, Amy racked up over $1.3 million in winnings, making her the most successful woman to ever be on the show. And her run is the second longest winning streak in jeopardy history.

Amy Schneider  30:18

When I lost that game, and my streak ended, and one of the contesting coordinators was kind of like walking me back. And I was like, really just sort of devastated by it, it had just happened. And she was like, you know, it’s like the end of the run of a show. All of you have put all this into this, and now it’s over, and they’re tearing down the sets, and you’re returning the costumes and it’s just over. And not just that, but like a show that keeps going on without you, you know, because then I was done. And then there were two more games that day, and I just had to sit in the audience and watch them and not be on stage for them and that was tough.

Stephanie Wittels Wachs  30:50

You were the understudy again? Perhaps one of the most mind bending parts of this experience was that Amy got on stage, she broke all of those records, she won over a million dollars. And the world didn’t know. And they wouldn’t know until months later. And now Jeopardy is this truly unique world, right, where everything’s filmed ahead of time, you’re doing multiple games in one day. You’re sworn to secrecy,

Amy Schneider  31:24

Indeed.

Stephanie Wittels Wachs  31:25

Until the episodes come out. So you had this like, wild to fold situation of basically knowing that you’re about to be famous. You were like, I broke every like, hello, I’m a record breaker. And you just have to sit with that.

Amy Schneider  31:44

Yeah. Yeah, no, and you really do that you’re sworn to secrecy, and they do not give you your prize money until after the episodes have aired. So that they can hold that over you? And if you yeah, like they technically could withhold your winnings, if you like, leak the results. Yeah, yeah but I mean, I think I’m also glad about that, I’m glad I had a bit of time to prepare myself for that. Sort of mentally, and especially because, you know, the fact is not just that, I was sort of, you know, I had the second longest streak of all times, and things like that, but that I was demographically different from everyone else would have my level of success being a woman being trans in particular, at a time when trans issues were, as they’ve continued to be, but this is like, sort of, early on and sort of the the kind of trans backlash that we’re living through. It was frightening, like, to be honest. I had been okay with going on TV as a trans person, because I just thought I was going to be on Jeopardy for a game or two. Like, the only things I was thinking about were like, would I feel dysphoric watching myself and seeing myself on TV like that was that was the only downside I was worried about. And then realizing that I was going to be, you know, in in the headlines and things like that, and you know, was going to be become a target for people. And so that was, that was something I had to get comfortable with pretty quick. And, you know, again, thankfully, because everything was taped in advance, I didn’t let myself think about that until my streak was over. You know, there was no studio audience, I was able to just divorce that from my mind. Because, like, you know, it’s not like, again, this was the only chance I was ever going to have to make $150,000 in a day and I wasn’t about to let any, you know, sort of fears of like Twitter trolls, like distract me from that opportunity.

Stephanie Wittels Wachs  33:49

Yeah, they’re not getting $150,000 in a day, that’s for sure. Stay there for a second. I’ll be back with you momentarily. Right? What happens when it finally does happen? It airs your success starts to trickle out into the world. You now don’t have to live this double life. When do you remember feeling like, okay, my life has changed. I this is this is a thing.

Amy Schneider  34:19

I mean, I think one of the big moments was, um, so a few weeks into my run. I got I mean, I got I got mugged I got my purse stolen in Oakland. It was nothing to do with being on Jeopardy it was just a random random thing. And so I just posted on something on Twitter saying that oh the my usual like things that I post are gonna be delayed a bit because I just got robbed. And then I got a bunch of like, texts from like friends and family saying, oh my god, are you okay? I just saw the headline, and I was like, the headline. And you know, then I go Google my name and there’s all these little like clickbait articles about like Jeopardy champion Amy Schneider robbed In Oakland, and yeah, and I mean, it was, you know, it had already started to be a funny thing that I had noticed, you know, because I had Google Alerts on my name, of course. And just all these, again, like SEO optimized headlines would say, Jeopardy champion, Amy Schneider reveals such and such, and it would just be, you know, a paragraph wrapped around something I posted on Twitter. I was like, I didn’t reveal that I just said it, you know.

Stephanie Wittels Wachs  35:28

The rich and famous over here.

Amy Schneider  35:30

Yeah. Yeah. But yeah, but just that realization that I had, you know, that I was a public figure in that way and if I did not want things to be put into clickbait, you know, news articles, it was up to me to maintain that boundary between my private life and my public life, because, you know, it was all sort of fair game. I mean, I loved being famous, I think it’s been great I love people paying attention to me and telling me how great I am all the time and all of this and asking for my picture. But it is something that I cannot pause, and I do not have the ability to stop it. I can’t turn it off, like flipping a switch I can sort of like if I wanted to, I could do the thing where you like, tell your computer to turn off and then it’s like installing updates for a while and things like that. And it’ll eventually turn off, like if I really liked withheld myself from the public, eventually it would fade out. But it’s not entirely in my control. And that’s been an adjustment.

Stephanie Wittels Wachs  36:29

Sure. When do you officially quit your job and kind of step into this new phase of strange life?

Amy Schneider  36:38

Yeah, well, I was I mean, the fact is, it’s like I’d already during the course of my Jeopardy run, gotten demoted, because I was really not doing my job at all, at that point, like it had been struck. I had been struggling to care about my job for a bit. And then when my Jeopardy run was happening, it got really hard to care. I’ve been planning to stick around for like, a couple of months, my run ended in January and like, in April, I was gonna get a bonus or something like that I forget what. And then like, one day, I was like, okay, I really have to write this leg, RFD document and get it up done by tomorrow. And I was just looking at it and looking at it, I was like, you know what, I’m not going to do this. I’m just not going to write this document. I’m quitting. Like, I just cannot do this anymore. I don’t care. And so yeah, and so that that was kind of the moment, you know, and it was certainly frightening and remains frightening. Because while I won a lot of money, and I’ve set for a few years, between taxes and like Bay Area, cost of living and things like that, it’s not like it’s enough to retire on. I don’t want to have to go back to a day job. And so I’m going to have to find ways to find new income streams going forward. And, and it’s frightening. It’s frightening not having a salary. Even though I’ve got the cushion that I can afford not having a salary for a while, it’s still scary that as of right now, I don’t know when my next check is going to come in for anything. I’m confident that something will but I don’t know what and I can’t guarantee it. And so it’s thrilling, but it’s definitely stressful in a way that I this was never something I plan for my life. I just thought I’d be a, you know, computer programmer for 40 years and then retire. And that would be it.

Stephanie Wittels Wachs  38:31

Post Jeopardy. Amy’s life has been full of things she never could have expected. Like, for example, just how much money would come out of her winnings and taxes courtesy of the state of California, or that she’d be happily remarried to a wonderful woman named Genevieve. She also couldn’t have expected how perfect it would be for this dream to come to fruition after she transitioned, which for a while was actually her biggest nightmare.

Amy Schneider  39:01

I thought it was going to be an exciting, you know, a couple of months, and then that will be it. I did not expect to be coming up on two years later, like doing this podcast here and talking about it, having written a book haven’t done all these things. But I think you know, what I really remember about it the most is, as I said, I was afraid of like being targeted. And then like trolls, and all these sorts of things. And not that that didn’t happen at all, there was some of that and it was hard not to take it personally. But there wasn’t much of it a lot less than I expected. And a couple of weeks in awhile by you know, not even that far into my run. I got a message on Twitter from a trans woman saying that her you know, I think her dad or grandpa or something like that had started gendering and naming her correctly after seeing me on Jeopardy, and that was not something I expected. And I have have heard over and over again sort of similar stories from other people about how they’re their relatives or themselves, kind of like, understood trans people because of seeing me on Jeopardy. I didn’t think that that was all it would take for so many people. But in retrospect, I realized that it kind of been true for me, you know, everybody, my age older, everybody who was born in the, in the 20th century, was raised with these beliefs and stereotypes about trans people as deluded men, as jokes as serial killers is whatever else. But then I moved to the Bay Area, I met Simon I was like, oh, well, that’s not true. You know, they’re just people, and they’re not weird. And so it had really been that simple for me and so it turned out it was it was that simple for a lot of people who saw me on Jeopardy, because, you know, there’s not that many trans people out there. Most people, you know, haven’t encountered one don’t know, one as a person. And so they only know the stereotypes they were raised with and the scary headlines that show up in their Facebook feeds.

Stephanie Wittels Wachs  41:08

Yeah, that representation of like, trans people go to the grocery store. Transpeople win Jeopardy. See, seeing you in such a sort of normal, typical environment on a show in my living room?

Amy Schneider  41:23

No, I mean, it’s what I say is like, there may be no more normal thing to do in America than beyond Jeopardy, certainly in a way that you can become famous for. Yeah, yeah.

Stephanie Wittels Wachs  41:32

So wholesome in every living room in Ohio.

Amy Schneider  41:38

Yeah, yeah. I mean, not every living room is funny, you know, growing up watching Jeopardy as as so many Jeopardy fans have watched it their whole life, and we’ll just sort of assume that like, everybody watches Jeopardy, and then becoming Jeopardy famous. I found how that that is not true. You know, all the time, it will be a thing like I’m getting checked into the airport and the agents like, Oh, my God, hey, your your Amy right? And I’m like, yeah, they call their coworker. They’re like, hey, do you know who this is? And they’re like, No. on Jeopardy, okay.

Stephanie Wittels Wachs  42:12

Listen, keeping you humble. Keeping your feet on the ground. Jeopardy famous. I love it, I love. I mean, there are probably very few people who are Jeopardy famous actually, like, who are legitimate and crossover to the mainstream?

Amy Schneider  42:31

Yeah, no, it’s it’s a small club, and I am now you know, friends with most of them.

Stephanie Wittels Wachs  42:41

I mean, your story is so it’s so exciting and beautiful and like I said, complicated. And, you know, in your early life, sort of struggling with that, with that concept of like being smart, and what you’re talking about in high school grappling with what’s not cool to be smart. It’s not, you know, and now your entire life has been up ended, because of this amazing intellectual prowess that you have. Right? It’s an amazing story.

Amy Schneider  43:14

What is and I think too, though, like the the parallels of it are, you know, it’s not just the smart thing, you know, I did not succeed in jeopardy, just because I was smart, and knew a lot of stuff. Obviously, that was huge. But I wouldn’t have been able to succeed had I not, you know, if I had, if I had been on Jeopardy, before I transitioned, I would not have done as well, if I had not done the sort of work on myself for all of that I would not have done as well, even if I had done as well, I would not have been prepared to be a public figure, I wouldn’t have been able to, you know, had the courage to quit my job and to pursue other things I wouldn’t have had the confidence to to write a book and put it out there and believe that what I had to say was worth saying, I did this James Holt’s our fellow Jeopardy champion does a fundraising thing in Las Vegas every year, and I did a panel with some of the other Jeopardy champions. And a lot of people they’re asking, you know, tips and tricks for how to get on the show how to do well. And, you know, I really felt that one of the things I wanted to say is you need to care about it less. Like if all you’re focusing on is this and you’re putting all your eggs in this basket, then A there’s a good chance that you’ll get on and you’ll lose your first game, and that’ll be that and it’ll be a waste and B it’s gonna make you less likely to win. I think that it’s not a coincidence that the Jeopardy champions are not the sort of one dimensional sort of trivia nerds that you would sort of imagine as the stereotype. I’ve gotten to know a lot of them like we’re friends and we’re all like, fascinating, well rounded people and that’s not an accident.

Stephanie Wittels Wachs  44:52

Yes, and the great part of your story, there’s so many great parts, but how everything there really are no everything started to fall into place, meeting Genevieve and getting married and feeling comfortable in your skin and, and then winning. I mean, it all does sort of weave together, doesn’t it?

Amy Schneider  45:10

Oh, it definitely does. I mean, there are times in the last few years where it’s like, I’m like, I understand now how, like cult leaders can really believe themselves to be like Jesus Christ or things like that. Because it is absurd, how well things have worked out for me, like, raising.

Stephanie Wittels Wachs  45:34

But even like the fact that, you know, it’s absurd.

Amy Schneider  45:40

To be clear, I do not consider myself to be the recordation of Jesus Christ.

Stephanie Wittels Wachs  45:48

You know, there’s an interesting part of this, where you’re saying, like, I don’t know what’s next, right? I’d love to sort of get a snapshot of today. And then when you envision down the road, like, what are you seeing?

Amy Schneider  46:01

Yeah, you know, it’s like, people ask me, you quit your day job what do you do now? And my answer is, generally, whatever this is, whatever I’m doing right now is apparently what I do. And so yeah, I think it’s, you know, I run a small business, the small business of Amy Schneider, you know, LLC, in fact. And, like, a lot of my life has been kind of like consumed by writing this book. And I’ve loved that as much as I complained about it the whole time, my hope is to, you know, be able to write another and to continue writing as sort of like, my main thing would be, you know, sort of ideal. And so that’s kind of what I’m trying to orient things around is how can I structure my life, to make that work to make that possible to make money at it. And at the same time, I can’t tell you what I’m going to be doing next year, I simply don’t know. And that, you know, is certainly terrifying in a way. But I used to set such limits to the things that I could fantasize about, and dream about, and imagine what I could do. And I’ve learned that that was wrong, there are an infinite number of ways that my life could play out. Even before being on Jeopardy. I could never have imagined moving to the Bay Area, I could never have imagined becoming out as trans. I could never have imagined so many other things happening in my life. And they did and they’ve been wonderful. And so I now think that there are going to be more things that happen that I’m not imagining now. That will be more amazing things that I will just find out what they are when they happen.

Stephanie Wittels Wachs  47:42

What’s the Shakespeare quote, there are more things in heaven and earth than to be dripped. What is it dreamed of? What is it that?

Amy Schneider  47:49

Are dreamt of in your philosophy? Horatio? Yeah, yeah.

Stephanie Wittels Wachs  47:54

I love it, I could ask you and you told me the right answer.

Amy Schneider  47:58

I mean, it is sort of my thing.

CREDITS  48:10

There’s even more LAST DAY with Lemonada Premium. Subscribers get exclusive access to bonus content like an AMA with yours truly. AMA stands for Ask Me Anything in case you didn’t know. So just FYI and FYI means for your information. So subscribe now in Apple Podcasts. LAST DAY is a production of Lemonada Media. The show is produced by Kegan Zema, Aria Bracci, and Tiffany Bui. Our engineer is Brian Castillo. Music is by Hannis Brown. Steve Nelson is our Vice President of weekly content and production and Jackie Danziger is our Vice President of narrative content and production. Executive Producers are Jessica Cordova Kramer and me Stephanie Wittels Wachs. If you’d like what you heard today, we have three other seasons that you can check out. Have a story you’d like to share, head to bit.ly/lastdaystories, or click the link in the show notes to fill out our confidential Google Form. follow and subscribe wherever you get your podcasts or listen ad free on Amazon music with your Prime membership. You can find us online at @LemonadaMedia and you can find me at @WittelStephanie. Thank you for listening, we will see you next week.