Mallory Ortberg on being a writer online, her love of The Simpsons and how to respond to criticism.
As editor of feminist literary website The Toast, Mallory Ortberg has carved out a lucrative niche for herself, covering #highly #relatable topics such as Which Jane Austen heroine are you?, Why are you lonely? And Grumpy Hermits I would like to cuddle in Art History.
Three years ago she turned down a job offer from The Atlantic to start The Toast with her business partner Nicole Cliffe, whom she met while writing for The Hairpin. Her style is wry and often involves poking gleeful fun at jerks in Western art history and literature. Her book Texts from Jane Eyre and Other Conversations with Your Favourite Literary Characters reimagines conversations between beloved fictional characters as if they occurred in the modern age of WhatsApp and “nm, wbu?”
Currently in the country for Writers Week, we caught up with Mallory to learn more about her work.
Reading through all of your work you have so many unique ideas and it is clear that you also consume and read a lot of media. How do you find time to write, as well as find that inspiration?
It helps to have a lot of deadlines on a daily basis. The more I have to write, the more I have to read and it sort of feeds itself, if that makes any sense.
I had a really classical education in a lot of ways. I grew up reading a ton of stuff about western church history and Greek and Roman and Persian mythology and a lot of the books of the western canon, so I feel like a lot of what I do now is just riffing on the things that I learned as a child.
I was also an English major so I’ve always been a big reader. It’s the kind of thing where it’s your job to come up with three things a day. You come up with ideas or the site doesn’t have any work, so you have to do it.
Did it take you long to get into the rhythm of posting three times a day?
A little bit. Definitely in the year or two leading up to starting the site I was writing a fair amount on the weekends, as well as my day job, so in some ways I was fairly prolific and obviously there’s a difference between that and posting every day, but it’s a sort of rhythm that works for me.
It’s easier for me to have a lot of little goofy ideas and you can riff on them and then move onto the next than it is for me to spend a really long time on an essay developing really thoughtful ideas. I’d rather make a bunch of quick jokes and then move on.
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How would you describe the tone of The Toast?
On the one hand, I think it changes all of the time because I think the tone is just whatever Nicole [Cliffe, co-founder of The Toast] and I feel like talking about. It’s not as if we sit down together every morning and say, ‘Now what is The Toast’s tone on such and such a topic?’ but, I would say in general we try to discuss things with a fairly light touch.
That doesn’t mean that we don’t take things seriously, but it means we try not to take ourselves too seriously.
What was the pitch for The Toast like in its early days?
Luckily, since we didn’t [need to] go out and get funding we didn’t have to do the elevator pitch too much, which is great, because in the early days I was mostly just like, ‘Just read it, it’s going to be great. Now go away’, which is not a great pitch for a site.
But yeah, we had a vague idea of what we wanted to do and we also felt like, ‘Well, I think that the things that we like other people like and I have a feeling that if we start talking about it, they’ll show up’.
Where did you find that self-assuredness? How did you just know it was going to work?
Nicole had been one of the editors at The Hairpin at that point for at least a year and a half, and I had been writing at Gawker and a couple of other places, so we’d both already built a bit of an audience, each as individuals.
So we knew in some ways it was a calculated risk, it wasn’t just a leap off a cliff. We knew, “Okay we have an audience, we write about certain things, there are people who share these common interests and the style and tone”.
I think that was what made us feel like that would be do-able to try something just the two of us. We both had seen a degree of success individually that we felt like were five points in a good direction.
For you personally to have that degree of success it would have come with some confidence as well. How did you establish that or what contributed in building that confidence in yourself so early, and confidence in your work, as well?
I have obviously written some things that are good, some things that are not good, some things that needed a lot of work and I have been able to see over the course of my life as a writer. But generally the progress has been in a good direction, so I have been able to see my own work get better.
I think I have a fairly healthy self-regard, which is to say, I know my strengths, I know my weaknesses. I can point to ways that I have gotten better. I can see things that I can do really well and in general I just feel really good about my place in the literary world and I do work that makes me really happy. I think I have a great audience and sometimes I get a chance to improve on something that was harder for me in the past and that’s really nice.
I think sometimes the really standard narrative you hear about writers is just this ‘Oh, it’s so frustrating, it’s the hardest thing in the world’ and you’re always staring at this blank piece of paper and that’s just not really my experience. That does not mean that it is not true for some people, I just think it’s not inevitable as a writer.
I think I can separate my identity as a person from my identity as a writer pretty well. Generally I see writing as a job. Sometimes I do better than others. If I write something that is not great I just move on and write something else.
I understand that I am not going to do everything the absolute best way I can every time. That is okay with me, I just move on and do the next thing. If anyone out there is starting to write and are worried that they don’t feel enough anguish about the writing process, I just want to reassure you that you’re fine.
Do you think that publishing writing online is a good way for writers to develop their voice and their style these days?
It works really well for me, I can tell you that. I know that there are a lot of different ways to write online and there are pros and cons as there are with every medium. One thing that is really great about it is that you often have a chance to find an audience that works for you. Often there is a lower barrier to entry than in some other ways of publishing, so it’s sometimes a little easier to get your foot in the door, especially if you don’t live somewhere like New York City.
A lot of time when you’re just starting out it is very difficult to get paid much, if at all. I know in my own experience, probably the first year or two that I was writing I wrote mostly for free. That’s not something I would ever encourage someone else to do, but it did ultimately help me find other places that were able to pay me and provided me with a better and bigger platform.
But it was something that I eventually stopped doing.
Again, I would never say to someone, like, you should or shouldn’t write for free because the answer is a very personal decision and that depends on your own situation and obviously I think everyone should be trying to get as much money as they can, within reason.
They should be advocating for themselves as writers, but that’s certainly something that everybody has to answer for themselves. Am I going to write for free? If so, for how long? If so, for which publications? If so, is it reasonable that they’re not offering to pay me? Am I at least going to ask? So that’s a difficulty, for sure.
And then there is also a lot of online writing is geared toward … We know this perspective will get you clicks and in some ways people will sometimes feel like they wrote something that is excessively personal or took a stance they weren’t really sure that they felt, but they did it because they had to drive traffic. That is also part of the nature of publishing, right, everybody wants readers, but that’s probably a question for writing in general than it is for writing online.
With The Toast, do you have any expectations of your writers to be generating page views?
We don’t really talk to any of our freelancers about page views, because that is not really an expectation or burden that we want to put on them. It is certainly something that we learned as we went - that sometimes pieces we thought would do really well, in fact, didn’t. Or sometimes we would be surprised by some of the pieces that ended up bringing in huge traffic.
Generally, our monthly numbers are pretty good, so we try not to focus too much on individual pieces. Every once in awhile, one of the three of us will do surprisingly well and that’s kind of always funny and interesting to see what was the cause around that, but we try not to say to our writers like ‘Hey, your last piece didn’t drive enough traffic, so you personally are responsible for writing a big viral piece.’ It generally balances out by the end of the month so we feel like if we’re interested in a piece, if we think it’s worth writing, we’re not going to obsess too much over making sure that it brings in big clicks because I can always just write another bunch of jokes about guys wearing helmets in art history and that’ll take care of that for the day.
Tell me about the dynamic between you, Nicky [Chung, managing editor] and Nicole and the roles each of you have at The Toast?
Nicole and I are the co-founders of The Toast and we brought Nicky on about a year later and it’s so helpful. Nicole and I have talked about if you were to divide people’s work by Bert and Ernie, like from Sesame Street, you really need one Bert and Nicole and I are both Ernies. She had to be Bert in Bert’s absence and it was definitely not easy for either one of us.
Nicole spends a ton of time on day-to-day management of the site and handles all of the link round ups and works a lot with the freelancers. Nicky is our managing editor so she handles the bulk of our submissions and edits pieces from our writers as well as writes wonderful pieces for us.
She’s just so fantastic at helping somebody find the best version of their piece that exists. She can take something that is really good and take it in an interesting new direction and just is that fantastic kind of editor that makes your work better than it was before, but still remains yours. She is not the type of editor who will force a house style on you, but she will craft it.
I just have always been so impressed with her. I am so glad that we found her. I can’t speak highly enough of her.
We’re on opposite sides of the country so we talk on the phone a lot and email a lot and we all have different perspectives on things that I think the three of us together make a really excellent team. That’s really cool, because we all have such different strengths.
I noticed that there are a lot of references to The Simpsons in your work, so I am curious to hear how the show might have shaped your sense of humour or your writing style.
Yes, I do write a lot about The Simpsons, which is something I always feel a little stupid about, because “Oh look, another person in their late 20s thinks The Simpsons is funny”, like of course, we all grew up on it. We all quote the same sentences to one another. There are so many ways that that show is some of the best writing in the 20th century and just amazing and so perfect.
There are so many little Simpsons moments that I am constantly saying in my daily life and again, that sounds so conventional, like, “Oh, how shocking, a millennial who likes this very popular TV show from the past”.
One of my favourite lines is from the episode $pringfield, which is the one where Marge becomes addicted to gambling. At one point there is a throwaway gag where Bart opens his own casino in his treehouse because the manager of the real casino throws him out for being underage and there’s this little throwaway moment where the manager sees it and he runs away in tears, like, “Oh, he did show me!”.
With your series How To Respond to Criticism, I am interested in talking to you about criticism as well … how you feel about criticism and how you handle it, especially criticism from strangers.
I think, as one grows in this life you have to learn how to deal with criticism and I think sometimes separate the tone from the content of the criticism. There are times when I just want to dismiss what someone said because I don’t like the way that they said it. But it’s important for me at least to go, “Okay, here’s their tone, that’s separate, what’s the gist of what they’re trying to say, what’s the content, do they have a point here? Can I react to this?” Not defensively as if I am being attacked, but as if I am being given information. “Is there something here that I can utilise? Great, how can I use it? If not, how can I gently dismiss it?”
It can be so easy, especially if you lean towards being sensitive, being insecure, if you have the artistic temperament that is conventionally associated with being a writer, it can be easy to feel like my self-worth depends on the feedback of either people. So either, I am the greatest thing in the world or I am a maggot.
So it is sort of fun to write about it from the perspective of my worst self. The part of me that I try not to indulge. Like, How To Respond to Criticism is not how I act in real life, I do not do those things. At least not most of the time and not any more. But man, do I get wanting to make it illegal to even mildly criticise me! Other people can be criticised all of the time and they can just deal with it, but not me, obviously not me.
I think it is really important for everybody, not just writers, not just people who write online, to be able to enjoy a compliment without needing a compliment. That’s why I like to write about that, to point out how painful it can be if you don’t figure that out, because then you just spend your life like The Terminator, looking at people through a heat lamp, you know one of those infrared cameras, like you’re looking for a warm body to compliment you. “Can you give me what I need, can you approve of me?” Phew! That is tiring.
How would you recommend other young writers build up their resilience around criticism and recognise when certain criticism is worth taking on and sometimes isn’t worth the time at all?
It partly depends on what your goals are in life and as a person. It’s helpful to figure out, ‘What’s important to me? What do I value? What do I think about the world and the universe and what a good life looks like?’ Some of that is just a natural self-development as an adult, figuring out what matters to you and what doesn’t. Developing a healthy relationship with yourself and with your friends. There are times when I have done and said things that are just flat out wrong. I was just wrong.
Earlier in my life, like in college or in high school, it was easier for me to feel like if I had messed up, I was a bad person. Because when you think of things in those terms, it keeps you from growth. If you hear someone say, “You did or said something that upset me” and what you’re hearing is “You’re a bad person and you’re a piece of shit and you’ll always hurt people”, it’s not only painful, it also keeps you from being able to change, because from then of course, your goal becomes not, “How can I respond well to this, but how can I fight the accusation of badness? How do I rid myself of this accusation and stain on my soul?”
So you’re not able to absorb any information. You’re just terrified that someone is going to find out the real truth of you and expose you. It keeps you from actually becoming a better person.
You mentioned little failures earlier on when you were at university … what is your relationship with failure?
What do you mean, I have never failed! It is not anything I welcome. Certainly I don’t wake up in the morning and think, “Oh I would just love a chance to grow through failure today.”
I’m not that self-actualised.
It’s an important part of being a person. If I had to choose, even if I was trying really hard to be a good person, I’d probably choose success over failure every time. When it happens, it happens. You can have as big of a response to it as you want and you eventually just have to accept every situation that comes. It doesn’t mean that you have to like it, it doesn’t mean you can’t do your best to change it, but… I just really think, after you allow yourself to have an emotional response to something, you get to decide, usually, what you are going to do about it.
Sometimes it just sucks, sometimes you don’t learn anything from the failure, sometimes you just fail and that’s fine. I don’t think everything needs to be a lesson, I don’t think every failure needs to be turned into a greater triumph, I don’t think that is a useful narrative for everybody’s lives. Just, sometimes you’ll fail. You can’t always snatch success out of the jaws of failure. You can respond to it in a way that makes you feel good about yourself.
I can totally see why they asked you to be [Slate’s advice columnist] Dear Prudence!
Oh, that was one of the most fun conversations of my life, let me tell you!
How did that go?
It was totally shocking, I just got an email from the folks at Slate and they had said, “We’re looking to hire for this position in the next couple of weeks, I know you already have a job but if you were interested, would you consider being one of the people who applied for it?” I thought they were joking, I had not thought, “Man, what if suddenly that job was open?”. It was not something that had occurred to me, so I was so floored and so excited.
I talked it over with Nicole obviously and I did a couple of test rounds and I was over the moon when they made me the offer, so it has been so much fun to figure out. It was definitely tricky to figure out at the start, what is my Dear Prudence voice? How is it going to be different from the last Dear Prudence, how is it going to be different from what I’m like at The Toast? What do I want to bring to the column? So it has been super cool.
What is your Dear Prudence voice?
It is Mallory dialled down in terms of craziness about 30% and dialled up in wisdom about 30%. It’s definitely still me. It’s just slightly less likely to tell somebody to set something on fire or run away to the ocean, because while those can be fun rhetorical devices, they’re not always incredibly helpful when someone writes to you asking for advice.
You get all sorts of tricky questions …
Yeah, oh my gosh! Some of the stuff I feel like, “I can really relate to this, this is similar to my own experience”. Some stuff I really have to dig deep and think, “Huh, I’ve never encountered anything like this before, how can I relate to this person?”.
What kind of importance do you feel the readers place on Dear Prudence and the advice that they are looking for?
I don’t think very many people are writing into Dear Prudence, like, “Help me Obi-Wan, you’re my only hope”. Even if they’re going through something really, really difficult and painful, they often have other people or resources in their lives. They are often just looking for somebody who is not in their situation, who has a little more perspective, or even just a different perspective.
Often I think they already know what they are going to do or they have already decided what they are going to do and they want someone else to affirm that they made a good decision.
Sometimes it feels like they want someone to scold them a little bit. I definitely had a handful of letters that felt like they had a little bit of a chip on their shoulder and they felt like they wanted someone to say either “You’re brave and iconoclastic” or else rap them on the knuckles and say “You’re doing the wrong thing!”.
You kind of get a feel for it with each letter, a little sense of what the writer is looking for, what they need… if they need a gentle touch or an emotional response. Do they need something bracing and practical and say, “Snap out of it”? I try to intuit that from each letter.
Reflecting on advice that you have received and advice that you have given as well, what makes good advice?
I think that’s different for everybody, especially with an advice column. There’s a balance between being helpful to the original letter writer as well as being entertaining to the many many more people who are reading. Hopefully it combines empathy with sensibility, practicality and a few cloyingly gentle, “Oh you poor, sweet darling” and on the other hand not something that is unkind, “Get yourself together, you’re pathetic, get a hold of yourself”. Something that is affectionate and yet bracing.
What is editing The Toast like as a job?
There are times running The Toast where Nicole and I have to do administrative stuff, that we don’t love. We have to fill out forms sometimes and do scheduling. It is not what I get up in the morning out of bed for. There are a lot of ways in which I have had jobs where I had plenty of time to do creative stuff or I was able to be creative at work or I was able to build towards the job I wanted. There were a lot of steps that I took to get the job that I have now.
It’s not a job that is going to last forever. I have no illusions about the state of new media, or if I do I have fewer than I used to. I know that I won’t be blogging about art history on a daily basis ten years from now. I understand that things come and things go and I try to have a fairly clear-eyed outlook about that. I have hopes and dreams about things that I would like to accomplish and I also know that if I don’t get to do all of those things and I am going to be okay and still really enjoy my life.
This interview has been edited.