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In 2013, Courtenay Hameister, head writer and host of the hit syndicated radio variety show, Live Wire! Radio, had an anxiety attack so terrible that she had to step down from her decade-long position as host of the show. A longtime struggler with Generalized Anxiety Disorder and OCD, she realized that suffering through persistent extreme angst was ruining her health. So, with her newfound freedom, she decided the best thing to do was… a bunch of stuff that scared her.

As a way to try to manage her anxiety, she began writing a column for the online magazine GoLocalPDX, in which she experimented with activities that made her uncomfortable — like a sensory deprivation tank, a session with a professional cuddler, and a Brazilian wax. Build-Your-Own-Burrito Night at the sex club. Dating. I loved Hameister’s “Reluctant Adventurer” column and was very excited when I learned that many of her essays about these adventures were going to be made into a book. Okay Fine Whatever: The Year I Went From Being Afraid of Everything to Only Being Afraid of Most Things is a collection of surprising, sometimes brutal, sometimes blushworthy, sometimes heartbreaking, always hilarious essays told with honesty, insight, and ferocious wit.

Gigi Little: You spent a year doing things that gave you anxiety as a way to try to become less anxious in your life. One thing I noticed about this book is that you didn’t just make a list of random scary things and do them. You don’t bungee jump, eat a cockroach, let yourself get covered in spiders… It’s a very specific set of fears you take on, which feels way more personal. How did you choose which particular anxieties to tackle?

Courtenay Hameister: In some ways, it started off fairly randomly. Actually, when I said that I was going to write the column, I put it out on Facebook to my friends. I said, Hey, I'm writing this column. I'm looking for things specifically that are going to make me uncomfortable.

Someone suggested ecstatic dance, which I didn't end up doing. I went to an escape room. What started to happen was that I clearly was on this path where it wasn't just about things that made me uncomfortable; it was also about things that I needed to work on. Going to a professional cuddler was an idea that came from my editor, but when I thought about it, I recognized: Oh, this is something that could really illuminate something for me. 

I started to try to choose things like that. The sensory deprivation tank — I had heard that it can help creative people. During the course of the book, I was clearly struggling creatively as well. So, the process was random in its own way, but now as I look at the arc of it, I was obviously trying to fix some stuff about myself. 

Gigi: That’s interesting, because as a reader, I definitely felt that arc through the book. It doesn’t feel like a collection of individual experiences as much as a journey. But it sounds like there were things you did in the Okay Fine Whatever project that didn’t end up in the book?

Hameister: Yeah. It was really interesting because when I wrote the first draft, I put a lot of different stuff in there, like a Zumba class. Zumba was actually the first thing that I did for the column. I went to a cat café. That was uncomfortable because the person that I was going with was a date who didn't like cats. But the material that resonated emotionally with my editor was the stuff that in some way created a shift in me and I grew a little bit. 

The Zumba class… I didn't have an epiphany in the Zumba class.
Gigi: In the course of this project you did a lot of dating, something that you’d been avoiding for years. You used OkCupid and you made a spreadsheet and rated your dates on various traits.

Hameister: I'm the worst.

Gigi: Yes, you said doing this turned you into an asshole. I was curious about your strong feelings about the spreadsheet being a jerky thing to do, because I kind of thought it was a cool idea. So, I guess my question to you is, am I a jerk? 

Hameister: Yes.

[Laughter]

Hameister: No. You don’t know how much of a jerk you are until you do it. It's not until you are actually looking at it in black and white — or green and white with Excel — that you see that you're actually assigning a number to a person.

Part of my rationalization was that I felt like my categories weren't too dickish. I did rate attraction, but I didn't say he's this attractive. It was: this is how attractive I find him. He has an interesting job or he’s passionate about things and loves to talk about ideas: these were my categories. I’d come home from a date and I’d work on the spreadsheet and I’d think, It’s fine, it’s fine. Then I would know someone for a few months and look back at their number, and think, That’s awful! It really does feel like something that a villain in a John Hughes film would do.

What's interesting about it, too, is that the relative numbers shift as well. You meet someone new and suddenly the number for that other guy is much lower by comparison.

Gigi: See, that's fascinating!

Hameister: Then I realized about halfway through the process that I should have put in some categories that would take away from their numbers, like “still in love with someone else” was really important. “Completely not interested in me” was super important...

One of the categories was my overall attraction. That was interesting to me, because a man could have lowish numbers in other categories, but attraction, that thing that you cannot quantify… you can't even call it attraction because it has to do with your entire reaction to that person. Maybe it's pheromones. Maybe it's that he reminds you of someone in your past. Experts talk about how in relationships we are constantly trying to fix all of the things that are broken in our family of origin. So maybe a guy reminds me of my father, and I have this thing that I want to fix with my father, so I'm massively attracted to him.

For me, the difficulty was in trying to quantify the unquantifiable: First of all, it didn't make sense. And second of all, it felt dickish when a man that I loved was on that list. 

Gigi: Was there any point during this project where you just said, I can't do this anymore?

Hameister: The cuddler was definitely very difficult for me. That was something that I didn't feel like doing. Honestly, the dating part was where there were multiple times when I said, I'm done. I'm just done.

I had a friend. I remember seeing her at Thanksgiving of that year. I think I was talking about the cuddler, and she said, Why are you doing this to yourself? It just seems like you're making yourself miserable. It really did.

I felt ashamed. I thought, Oh, so I quit a job that was making me miserable, and I started a project that is apparently making me miserable. Am I just self-flagellating, here? I didn't stop after I had that conversation with her, though. It was too important to me to try to see it through, because of what I had lost with Live Wire. I didn't want to lose something that wonderful again.

Gigi: Yes, as the book opens, you tell the story about having the anxiety attack that caused you to stop hosting Live Wire! Radio. In some ways, it seems like joining Live Wire must have been a prototype of the Okay Fine Whatever experiment. As a self-proclaimed “professional nervous person,” how did you end up doing something so anxiety-inducing?

Hameister: I met Kate Sokoloff, the cocreator of Live Wire! Radio. She and Robyn Tenenbaum, the other cocreator, had just wanted me to do some copywriting in order to sell the show to OPB. I did what I always do. This is how I got into a band. This is how I get into a lot of stuff. I am not completely 100 percent sure that I want to or can do a job, but I quietly suggest that I might try. I asked, Do you guys have a head writer for the show yet? They didn't. I said, Maybe I could try?

And they let me try! It really was this series of, Oh, there's not anyone to do that. 

I actually auditioned to be the host of the show. I studied acting in college. I always thought I wanted to be a performer. Back then, when I initially auditioned, I wasn't having stage fright. It wasn't really an issue for me.

Gigi: Oh, interesting.

Hameister: I auditioned and didn't get it. Then, when Rob Sample, who was the original host, couldn't do it any longer, they said, Well, why don't we try Hameister? And so I did it for a decade.

The anxiety was something that built up. I've always had Generalized Anxiety Disorder, but as the show became more successful, I felt more pressure. We originally did the show once a month. That week of the show was always the worst week of the month for me. Then suddenly we're doing it twice a month. Now two out of four weeks of the month are miserable for me. That's when it became an untenable situation. That's when it actually affected my health — I had so much cortisol in my system all the time that it became really unhealthy.

Gigi: You hardly have time to recover from one week, and you’re rushing headlong into the next.

Hameister: Exactly. It absolutely was the frog in the pot thinking that he's in a Jacuzzi. I didn't realize how unhealthy I was until it really, really came to a head. Of course, as I say in the book, there were so many extraordinary things that the show brought into my life, and I felt so lucky to be doing it. It was insane to think about not doing it. Who would quit that job? It was one of the coolest jobs in Portland, if not the coolest, honestly, just by virtue of the people you get to meet and talk to. I learned so much. I got to ask all these unbelievably talented people how they did what they did. Who gets to do that all the time?

Gigi: If the Okay Fine Whatever project brought you to a place in your life where good friends were asking you why you were doing this to yourself, did you ever get to a point where it finally turned a corner and you thought, Hey, I think it’s actually not miserable anymore?

Hameister: Yes. The funny thing is that the column started winding down. The website got a little… different. I think a lot of people were leaving the site. And then I met Date #28.

I don't want people to think I thought, Oh, I met someone, so I’m done with the whole thing, everything's fixed. It's not fixed when you meet someone. In fact, being in a relationship, to me, just puts a bright light on the places where you're still broken. That's where all of your insecurities come out, all of your fears of abandonment. And that fear of abandonment is living in your head, going through all of the reasons why someone's going to leave you. 

Gigi: All the issues that you talk about in the book — self-doubt, feelings of inadequacy, body shame — they’re all illuminated.

Hameister: Exactly. I loved someone, and I wasn't sure that I deserved to be with him. That's when I really realized, OK, these are the things that I need to fix. And it’s not so much that they're things that I need to fix about myself. Really, they're things that I need to fix about the ways that I think about myself and my experience. 
Gigi: There are books that are similar to yours in which the writer goes on a journey where they do something particular for a year to try to change their life — but the difference is that those books tend to spin it like they get to the end and, abracadabra, their whole life is changed. Everything’s wonderful. When that’s just not true.

Hameister: Yeah. I hope that the title of the book lets people know that that's not what's happening. [Laughs] It's a little bit of a spoiler, right? 

Gigi: I like knowing that, though. As a reader, I am much more apt to pick that book up if I know that you're not going to try to sell me on the idea that all of my anxiety's going to go away if I read this book or do these things.

Hameister: Yeah. You have anxiety; is it just generalized or social? You don't have to answer that.

Gigi: It's… lots of things. Definitely social. Obviously, I couldn't get on the phone with you.
[Editor’s note: Gigi and Courtenay spoke in person.]

[Laughter]

Hameister: I've been amazed at the number of people whom I've told about the book, and whom I've known for a long time, and who are like, Oh, my god, it sounds like me! The number of people who have anxiety, and I just never knew. Obviously, the number is growing now, just with what's happening in the country. I think psychologists have named it “Trump anxiety.”

Gigi: When you started the project, you were just writing a column, and then at some point it turned into a book. When you started thinking about it as a bigger picture story, with an arc, did you have expectations as to where that arc might land? And were those expectations met by the end of the project?

Hameister: I had no idea where the arc would go when I started it. I didn't think it through that well. Like I say in the book, it was exposure therapy, but to the entire world. If you do that, you really should have a therapist [laughter]… Someone working with you and helping you decide: What's your goal with this? I talk about how I think that the biggest thing anxiety stole from me, and continues to steal from me, is optimism, my ability to hope for the best.

There's a psychologist who writes about grit. There were these people who were all fired from the same company. And this group over here totally thrived, and this group over here were just downtrodden, and it took them forever to find a job. What the psychologist discovered was that the people who thrived did so not because their skill set was better or they had better connections. It was because they had grit. It was because they were resilient. 

If you are a pessimist, your resiliency is affected by that. It is much easier for something to take you down. That's part of the reason why I had to leave my job. 

What I wanted at the end of the Okay Fine Whatever project was to try to see if I could figure out a way to make myself more resilient and optimistic. In the smallest way, I did. I changed my perspective. 

I can't say that I'm an optimist now. I'm not. I probably won't ever be an optimist. What was hugely significant for me was that I realized that I don't have to be an optimist. I lived the most interesting year of my life, I did things that I enjoyed, that were illuminating, that taught me things about myself and the world, and I did it as a pessimist. 

Did you read Moonwalking With Einstein? It’s by Joshua Foer. He was on Live Wire. I got to read his book and talk to him. For the book, he spoke to a memory expert who explained about how when we do the same thing every single day of our lives, what our brain does, because it's our most efficient organ, is accordion all those days so that they feel like one day.

That's why, if you've been doing the same thing for a couple of years, it feels like, Oh my god, did two years just go by? If you do something different every day, even something as simple as walking to work in a different way, then that accordioning doesn't happen.

I think that doing different things every day literally lengthens your life, or at least it feels like your life is lengthened. I don't like feeling like all these days have passed in one hour. That was important to me: to try to teach myself to strengthen that muscle.

Gigi: I love that. And I love that you came to the conclusion about things being interesting rather than scary. That's a huge shift. 

Hameister: That's part of the message of the book. People think, I can't change my life. I'm not going to jump out of a plane. I'm not going to bungee off of anything. I'm not going to learn to skateboard. The thing is you don't have to.

It changed my life to go to a sensory deprivation tank for an hour and a half. I think that we have our comfort zones, and all it takes is the tiniest little nudge just push it out a little. You just have to keep pushing it out a little at a time. You'll be amazed at the end of a couple of years how far out it's been pushed. 

I say this in the book, but I also recognize that it's my white privilege that allows me to go out and do stuff that scares me just for fun.

Gigi: So, what’s your next big adventure?

Hameister: Oh, my gosh. Honestly, the book tour is a big adventure.

Gigi: I wondered if that was going to be just as anxiety inducing as some of the things in your book.

Hameister: I'm going to have to really figure out how to manage my stranger anxiety. I have some tools in my toolkit, now, to deal with that. But that's going to be a big deal. 

My boyfriend has this old RV, and we're just going to travel down the coast in it. I'm not really a camper, so that's a big deal for me.

Also, I'm going to the Austin Film Festival in October. I did it last year too. I go there and I moderate panels. I've gotten to talk to people whom I admire greatly, similar to Live Wire. I wrote to the AFF and I offered up my services. I don't think in a million years I would have done that before Okay Fine Whatever.

It's on a smaller scale than Live Wire. I'm just sitting in front of maybe 100 people at the most, and the stakes aren't as high. I still get to meet these extraordinary people and ask them about how they do what they do and learn from them.

Honestly, after going through this whole process, I can say that while the experience itself was significant, writing about it absolutely made all of those messages land. And all of it together enabled me to get back a little bit of what I'd lost — a little piece of what I used to do and the parts of it that I love. I feel like moderating at the AFF, and hopefully other projects like it, will be the next professional adventure that I get to go on.

I spoke with Courtenay Hameister in person on July 2, 2018. Courtenay Hameister is a professional nervous person. During her 12 years as host and head writer for Live Wire, a nationally-syndicated public radio show, she interviewed over 500 intimidating people and wrote 200 personal essays in bursts of anxiety-fueled inspiration at midnight the night before each show. Her work has also been featured in McSweeney's, APM's Marketplace, More Magazine and some scathing emails to the customer service department at Macy's. Okay Fine Whatever is her first book.