Going the Wrong Kind of Viral: Q&A with Andrea Askowitz

Andrea Askowitz

Author, editor, and podcaster Andrea Askowitz (@andreaaskowitz) discusses what she learned from going the wrong kind of viral, the power of vulnerable truth in writing, and whether she would rather be famous for her writing or good at it, if she had to choose one or the other.

Askowitz is the author of the memoir My Miserable, Lonely, Lesbian Pregnancy (Cleis Press) and the editor of Badass: True Stories, the Double Album (Lominy Books). She produced a documentary about homelessness that is currently nominated for an Emmy and founded Lip Service, a Knight Foundation award-winning night of true stories, which she produced quarterly for nine years. Now, she is the host of the podcast Writing Class Radio. In just five years, the podcast has been downloaded more than 650,000 times.

Her work has been featured in The New York Times, Salon, The Rumpus, Huffington Post, Glamour, AEON, The Writer, Manifest-Station, Mutha, NPR, PBS, and numerous anthologies.


KRISTEN TSETSI: You join Barbara Ehrenreich, JK Rowling, and Lauren Hough, among others, in the unenviable club of authors who have gone viral for the wrong reasons. Your piece in the Independent, about being a rule-breaking, lockdown-flouting entitled American, received a lot of negative attention, including Damon Young’s response essay in The Root, “Andrea Askowitz Invents New Level of Whiteness, Writes the Worst Essay You’ll Ever Read.”

You couldn’t have imagined your piece would generate such a powerful response. What drove you to share that lockdown-era travel experience, what kind of reaction to the essay did you anticipate once you learned it would be published, and what was it like for you to see the actual reactions coming in?

ANDREA ASKOWITZ: Thank you for asking this question and for not cutting me out of your will. I’ve been thinking A LOT about cancel culture and my role in it. I hurt a lot of people and I am really sorry.

What I meant or tried to say in my lockdown-era travel story got totally lost, and now I see why. When I got the piece published, I didn’t expect a reaction at all, which I’m totally embarrassed to admit. I was accused of being tone-deaf, among many accusations. It’s true, I was tone-deaf.

My point was that biblical idea that whoever is without sin should cast the first stone. I judged a man for breaking lockdown rules, then when I broke lockdown rules, I became that man. I had no business judging. I was trying to say we are all hypocrites. I was using myself as the example. I thought people would see themselves in me.

A year later, I realize EVERYTHING about my story was wrong, maybe even the central premise. Stones were cast at me. And while I do not condone meanness, I may have deserved the stoning.

It’s odd to say this, but I think I came out the better for it. I was accused of being privileged and of saying something racist. I hate the racist part the most. But I learned something, and that is why I’m better for it. The privileged part is more complicated because coming out okay after being slammed online for my privilege is probably only possible due to privilege. I didn’t lose my livelihood. Many people do.

Damon Young did a good job. His story is funny. I hate that it’s about me, but it’s Young’s job to call out racism. He’s built a career around this. He didn’t just fly off and call me names, like so many people did online. Young made me think, and in the last year, I have done a lot of reading and tuning in to what’s going on for people of color. The Black Lives Matter movement helped me understand what police brutality really means. I had an idea, but now I know that there is a long and terrible list of people of color who have been brutally treated by the police. So many people have been killed by cops. I never trusted cops, but I didn’t understand how dangerous it is to be confronted by a cop if you are a person of color. I also didn’t understand that some people—because of how they were raised or because of the color of their skin—won’t or can’t ask for what they want the way my wife, Vicky, did.

I’m afraid to stir up anger again by explaining what happened, but it doesn’t really make sense unless you know that Vicky was stopped by a cop at the border of Monroe County, which is the entrance to the Florida Keys. Our kids and I were quarantining at my mom’s house in Key Largo. We’d been separated from Vicky for more than two months because we had just returned from Spain. When the pandemic started, Vicky was in the U.S., while the rest of us were in Madrid.

A few days after returning to the U.S., the kids and I scheduled COVID tests. Vicky had our car and headed down from Miami, where she was staying separate from us (we were trying to do the safe thing), to take us to get our tests. She was stopped at the border because Monroe County restricted tourist entry. This was not a black-and-white case because we weren’t tourists, exactly. Vicky demanded that she be let through. The cop was mean to her and held her up, and this was the big mistake I made. I wrote that she experienced police brutality.

Vicky is Latina and considers herself white. She demanded to get through, which I understand, now, has everything to do with her being able to pass as white. I now know what Vicky experienced was not police brutality. I also know that naming what happened to her as police brutality diminishes other people’s real and sometimes fatal experience.

What was your takeaway from the reader response, both on a personal level and on a professional level?

At first, the response shocked and scared me. I could not speak. Not even at home. I was so afraid to say the wrong thing. Like, I’d say, “Pass the salt.” And then I’d think, Oh no, did someone else need it first? Did that come out entitled? I questioned everything down to who I am and who I thought I was. I thought I was someone who challenged society to be more just.

I am afraid to say what I’m about to say because I know this sounds like virtue signaling (something I’ve learned since my story came out), but before writing full-time, I spent many years working full-time as a social justice organizer and activist. I thought my heart was in the right place. And maybe it was. The problem was that my brain was in another place.

This is the problem with perspective. I was limited by my perspective. I didn’t know what I didn’t know. This whole experience helped me broaden my perspective.

On a professional level, I got lucky. I am lucky. I didn’t lose my livelihood. My wife was threatened and that was scary, but her boss stood by her. So, in the end, the worst part of being cancelled was that I silenced myself.

Your Twitter bio says you’re seeking an agent for a new memoir. Your debut memoir, My Miserable, Lonely, Lesbian Pregnancy, published in 2008, is about subject matter made clear in the title. Can you talk about the new one?

I’m working on two projects. One is ready to go out to agents and editors. It’s a collection of linked essays currently titled No One Knows I’m Famous or maybe it’s called She Married a Jewish, Gringa Attention Whore about my relationship with Vicky and how I risked everything when another woman gave me the attention I thought I deserved. I think I come as close to anyone I’ve ever read in telling the truth about a marriage.

My other project is a memoir titled The Year of Living Spanishly. In September, 2019, we took the family to Spain to learn to live less like spoiled Americans. Six months later, we were shut inside our Madrid apartment because of COVID-19. When we returned home, five months short, I was no less spoiled. It took getting reamed on the Internet to teach me a lesson I needed my whole life.

What attracted you as a writer to memoir writing? And what attracted you as an individual to the idea of telling your personal story?

I am fascinated by the truth. I also like how truth can become art. It’s sort of a miracle when someone goes through something terrible and can come through it and also create something beautiful out of that experience.

Telling my stories helps me feel connected. On Writing Class Radio’s first episode, I tell the story of what happened to me when I took my first memoir class and revealed something embarrassing. Basically, I threw myself at a man. I begged for sex. He said no. I know, I’m a lesbian. I know. There was a lot about that moment that humiliated me. I was at a low. Okay, I was desperate and pathetic. I actually swore I wouldn’t tell anyone what happened, ever. Then I wrote about it the next week in my writing class and then read my story out loud. What happened changed my life. I felt understood. Loved even. This is why I’m attracted to telling my stories.

What are some memoirs you’ve read that have helped guide your own memoir writing, in terms of how to creatively approach one’s own life?

Joyce Maynard’s memoir At Home in the World is a wonderful example of structure. It’s just logical, in my mind. Her second memoir, The Best of Us, is also instructive for structure and all things storytelling. She’s one of my best teachers. She’s just a brilliant storyteller. I also just finished Lauren Hough’s Leaving Isn’t the Hardest Thing, and there were so many moments when I thought, yes, this is why I read and write.

Many years ago, I read The Things They Carried by Tim O’Brien. And while it’s not billed as a memoir, I know it’s based on his experience. I loved how his stories built on each other. I love this book so much because I despise war, but I felt for his characters. Structurally, the way his characters show up again and again in new ways fascinates me. I also loved how each story worked on its own.

I saw this again when I read Olive Kitteridge by Elizabeth Strout. Again, this is fiction, but storytelling techniques cross genres. I just loved how the characters came and went. Recently, Kristi Coulter’s Nothing Good Can Come from This actually helped me in how to creatively approach my own life because she took one subject, alcoholism, and built a love story around that subject. That’s what I am trying to do with No One Knows I’m Famous.

Speaking of fame, you asked on Twitter, once, “Serious question for #agents and #publishers: If I create a giant platform, why would I need you?” I imagine this was in response to the preference agents and publishers have for nonfiction writers with established platforms to help sell their work. What answers did you receive, and were you satisfied by any of them?

I directed my question to agents and publishers, which was more a rhetorical question. But some writers answered and the discussion was a lot more thoughtful than I expected.

Some said we don’t need agents and publishers. Someone else said we need agents and publishers for legitimacy, which has been my bias. One writer compared an agent to a realtor and explained that, technically, we could sell our houses on our own, but we’re not experts and we don’t have the contacts or the expertise with contracts and legality. I thought that was a solid point.

What sort of platform do you need to have, as you understand it, to satisfy an agent or publisher? Do you need more Twitter followers (is it that simple?), or are you supposed to cultivate a platform more narrowly aligned with the subject matter of your new memoir—and how do you feel about that? Have you started planning how to do it?

What I understand about the business of publishing is that you have to have people who will buy your book. I don’t like that this is the case, but it makes sense in our current marketplace. The whole world is vying for the whole world’s attention at all times. And because people get their news and entertainment from specific, personalized channels, authors have to create our own channels.

In 2006, I created Lip Service, a live storytelling show, and I needed an audience. My mom gave me her personal mailing list, which included about 300 friends and family. I emailed my mom’s list and about 65 people came. Every show after that, I passed out a sign-in sheet, asking for people’s emails. I announced from the stage that I was taking attendance. When I go to a restaurant and have a fun conversation with a server, I ask for their email. I was/am very assertive about my mailing list and most people sign up when I ask.

This is exactly the same challenge authors have. We need an audience to buy our books. In the last 15 years, I’ve built a pretty strong mailing list, which I add to every week. Now, I have about 9,000 people on it, which is pretty much everyone I’ve ever met.

I’m also active on Twitter and Facebook. I’m bad at Instagram. And because I have a teenager, I’ve recently been introduced to TikTok, which I actually don’t hate. TikTok is fun to watch and fun to make videos. In a way it’s a more honest medium because it’s not about creating relationships, which to me can feel fake. TikTok seems to be all about producing content. Everyone is saying: Look at me! Look at me!

A few years ago, I set out to become Twitter famous. I spent a summer tweeting hard. I write about it in She Married a Jewish, Gringa Attention Whore. At the end of my Twitter summer, I got to about 6,000 followers and then slowed down. I failed. Now, who knows. Maybe this will be my TikTok summer and someone will finally know I’m famous.

I think what agents and editors want is not necessarily a giant number of followers, but an active presence, which would include a large number of people who engage with you. If you can position yourself as an expert on the topic of your book on social media, that’s awesome. Ashleigh Renard, a sex advisor on Instagram, has gained a lot of followers.

Writing Class Radio, the podcast I host, has been downloaded more than 650,000 times in five years. I get about 10,000 listeners a month. So, I do have a loyal following. I also give writing advice on social media, which is almost, but not quite, as sexy as sex advice.

Agents and editors are also looking for stories that hit a nerve and go viral. So, I write and send out essays for publication.

You also put some of them on Medium, and in one Medium essay, about your challenge to yourself to write one essay a week for a year, you write that you asked yourself during week 32 why you’d challenged yourself that way. Your answer was, “I’d finished a book and spent three years revising it with an agent. She sent it out to 12 publishers and it got rejected. Then my agent lost confidence in my book. I sent it out 26 more times. All rejections.”

What were those three years like? Specifically, were submissions ongoing throughout the revision process with changes being made according to editor critiques, or did submissions not begin until the final revisions were complete? And how did you feel about the agent’s revision suggestions when they were made—did you agree they would improve the book, or did you feel pressured to comply because “agents know what publishers want”?

I love a collaboration. LOVE. I don’t always agree with every note I get from editors, or, in the case you’re asking me about, my ex-agent, but I always appreciate and consider their feedback. Usually there is something that can be improved in the place someone notices a problem. So, when my agent asked me to rework, I reworked.

The process was too slow on both our ends. So that was frustrating. But, she would give me edits and I would revise. She kept saying, “Leave some blades open.” I may be a little dense, but it took years to understand that she meant: don’t kill the tension by tying up each issue at the end of every chapter.

While I was revising with my agent, we were not going out to publishers. A lot of time was wasted, and in the end, that’s why I left. She lost faith in my book, but I lost faith in her, too. I didn’t think she worked hard enough. I had the wrong agent, and I’m now looking for the right agent.

So, yes, A LOT of time was wasted. But I also believe that my book wasn’t ready. Writing a good book is hard and takes time and experience. I know that book number three, my next book, will come easier and faster because of the work I did on book number two, which I’ve heard is often the hardest.

This is a building process. Writing and building a career takes hitting a lot of balls against the backboard. To someone who is frustrated by the time it takes, I’d say: You have to love hitting the balls. If you don’t, get out of the game.

Have you ever considered, or would you ever consider, self-publishing?

I’m considering this option more and more. But I still want an agent and I still want to publish with a publishing house. It doesn’t have to be big. But I also want an editor. I love collaborating. I think my book is ready to hit the shelves, but I also think it would become a better book with a trained, professional agent and editor behind it.

How do you, as a reader, perceive work that’s self-released—written work, specifically, because it’s perfectly acceptable to self-release other art, like music, sculptures, paintings, etc., without the associated stigma?

You make good points about other kinds of art going public without any gatekeepers. I have an old-fashioned biased against self-published work. I need to get over it, because I realize that writers are going outside the gates all the time and if they’re good, they get readers.

Ashleigh Renard just put out a book called Swing, which sold 5,000 in pre-sales, which is pretty good. Renard has a strong following and she wrote a solid book about swinging. So, writers are self-publishing successfully.

But even Amanda Palmer got a publisher for her book, and she might be the poster child for crowd funding and independent producing. She taught the art world how to go straight to fans. So why, then, does Palmer’s The Art of Asking have a publisher, which is Grand Central Publishing, which is an imprint of Hachette? I think because even Amanda Palmer can’t reach as many readers alone as she can with a big publisher.

In a recent tweet, after expressing how it made you feel to give your work away for free (a Medium publication had published a piece of yours but didn’t offer upfront payment in return), you and I had a brief exchange that led to a broad question open to all writers: If you had to choose, would you rather be well-paid/famous for your writing, or be good at it?

Your answer was, “This is a hard one. I think…I think I’d rather be good. But then how would I know [if I were good]?”

I’m not suggesting you were doing this, but I see writers on Twitter popularizing a message that essentially boils down to, “If you think you’re any good, you probably aren’t.” It’s as if it isn’t enough to be humble; writers are, these days, supposed to self-deprecate and be ever uncertain of their skill. “I’m pretty sure I suck” is probably the only acceptable self-evaluation when it comes to writing.

And yet. Writers approach literary agents all the time, which they wouldn’t—and shouldn’t—if they really believed their writing wasn’t good enough for traditional publication.

Which brings me to my question: How would you know if you were good? How did you know you were good enough to submit your first memoir to a literary agent? How did you know you were good enough to offer writing advice on Writing Class Radio? How did you know you were good enough to post one essay every week for a year on Medium?

There must be a way of measuring skill. What would you say that measure is for you, and how might another writer seeking their first publication or representation answer the question, “How do I know if I’m any good?”

Can we talk for five hours? I know I’m good. I know because I’ve practiced and practiced. I also know because I read the competition. I don’t actually think of other writers as competition, but I do think of writing as a sport. Or I think of writing in terms of sports. I grew up playing tennis and running cross country. Both sports informed my approach to writing. As a kid, I’d hit 300 forehands and 300 backhands against a backboard for warm up. I knew that Bjorn Borg did that. He was the best player when I was getting started. He never missed. Writing 52 essays was my way of hitting against a backboard.

I know that not every story I write is good. I know there is a lot that goes into good, and that good is also subjective and that sometimes what makes a good story, even a great story, is not even good writing. It’s heart. It’s the willingness to tell the truth.

All that said, I was not self-deprecating when I wondered how I’d know if I were good. Some days I know I’m good. Then other days I’m not sure. I think Jews are famous for being equal parts confident and insecure. These opposing and frustrating qualities are good for any artist, especially writers, because it gives us the hubris to think we have something to say, and the insecurity to rework and rework whatever we’ve said until maybe it becomes pretty good.

I really wonder if I’d rather be good vs. famous. The right answer is good, I know that. But I’m not sure that’s my answer, because I really like recognition. This is part of what I explore in my memoir, She Married a Jewish, Gringa Attention Whore. I know it’s my Achilles heel. I know it’s stupid. This need for attention, recognition, fame, love almost cost me my marriage and my family.

Since we touched on the offering of writing advice in Writing Class Radio, and because choosing details is my second favorite thing (writing dialogue is the first), the episode The Devil’s in the Details discusses the importance of specificity in the use of details. If someone who listened to that episode needed a little bit more help understanding what makes a detail effective, how would you explain which details have more value and which can or should probably be left out?

I love this question, because while I understand the importance of including vivid details, I also love the process of editing out shit you don’t need. I actually get pleasure out of tightening a story down to its barest bones. So how do you distinguish which details to include and which to cut?

Details help a story come alive. Details are the parts we see. They describe character, place, mood, and time. For example, if you’re describing your childhood home, it’s a good idea to name the town, Miami, Florida. If you grew up in the 70s, mention the satin rainbow pillow on your bed and the poster of John Travolta you taped to your wall with Scotch tape.

Other details reveal character. A good way to get to those details is to answer the question: Like what? Or: In what way? For example, my dad is a mellow guy. Like what? In what way? My dad takes a nap every afternoon. His favorite book is Zen and the Art of Motorcycle Maintenance. He spent most weekends of my childhood shuffling around the house in a brown terry cloth towel skirt that fastened with Velcro.

If that last detail makes my dad sound like a creepy weirdo, I’d cut it. Details that almost always need to be cut are ones that read like travel plans. For example, if you are telling a story about traveling to meet your mother-in-law-to-be for the first time and you took American Airlines and arrived at terminal C early, but then American moved to terminal B for some reason and you had to walk the entire airport to find your gate and you started to run and got sweaty and then your flight was delayed, anyway, you probably wouldn’t include all those details unless those travel plans directly related to the story you were telling. I doubt they do. Everyone has an annoying time at the airport, so those details should probably be cut. Sure, you were nervous, but if you want to write about your nerves, tell us you were nervous in a way that specifically reveals your character. So maybe you bought a grey silk button down instead of your usual black because you thought you should spruce it up a little, and when you went to hug your new mother-in-law, giant sweat circles showed under your armpits.

Prior to starting the Writing Class Radio podcast, you were the head of operations for (and had created) the live storytelling program Lip Service. Writing Class Radio, like Lip Service, features writers reading their stories, but it’s followed by writing tips and host commentary to help listeners learn from the writers you showcase.

What motivates you to be a collector and presenter of writers and their writing for an audience of listeners and learners? And has what drives you changed over the years, since your start with Lip Service to what you’re doing at this moment with Writing Class Radio?

I love this question. For nine years, four times a year, I told stories on stage at Lip Service. Every time, after the show, I got surrounded by people who could not wait to tell their own stories. I was like, “Hey, can we talk about my story?” But so many people would just start telling me their own story. I couldn’t get through the lobby of the theater. It would take me an hour to get to the after party a block away because people were so jazzed. And then I’d spend the next three hours talking to people about their stories.

I realized that telling my stories inspired people to tell theirs. So, that’s how I built Lip Service.

I’ve always believed, and still believe, that stories connect people. I think storytelling is the best way to bridge differences. This idea has been challenged lately, especially with what happens online, but besides for inspiring people to open up, I saw in real-life people loving on each other, even when the stories told were controversial or hard to hear.

For example, we had a gay man tell a story about a time he met a guy through a dating app and ended up being asked to strangle the guy. The story was about how he was afraid he’d kill the man, but also how it turned him on. We had another story about a woman who came to Miami in 1980 on a Cuban shrimp boat. Her story ended with, “I am a Marielita.” That term is very heated in Miami. But both of these storytellers were mobbed after the show. They were admired and praised for their honesty and vulnerability. In both cases, I think they helped everyone in the audience—and I’m talking 500 people—understand something they didn’t understand before.

This is what I love about storytelling. I hope that when people hear stories on my podcast, Writing Class Radio, they are also inspired to tell their own stories, and I hope they learn something.

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