On writing, giving advice, and understanding yourself

You have a substantial Twitter following and sometimes your presence on Twitter intersects with your advice column. On Twitter success is quantitative—you post something and a lot of people like it. But with a column, it’s different. How do you know when you’ve succeeded?

I’ll blog on occasion and there are very clear metrics about whether that’s done well or not. You can see traffic numbers on the backend. The worst thing about blogging for a site where you also work is that you do end up having access to traffic numbers, and so you end up checking, which is a terrible habit to have.

My measure of if I’m satisfied with the column tends to be when I get responses from people either emailing me or messaging me on Twitter saying, “This really helped me in an aspect of my life.” It’s not often that you feel like there are real people reading what you’re writing and that it has impact on their lives. That’s always nice to hear, and definitely a function of an advice column—it being a little bit more personal and a little bit more intimate means that it tends to provoke more personal, intimate responses.

Your identity is at the front and center of the column, and your credibility relies on your experience of having self-identified as a fuck up. It’s this derogatory term that a lot of people wouldn’t want to say about themselves. Does that ever weigh on you creatively?

Yeah, “Trust me because I’m largely untrustworthy, or I have been for large parts of my life.” If anything, I always am vigilant against playing that up too much, like committing to the part a little bit too much because yes, I have woken up places that I shouldn’t, and I have made a lot of bad decisions. And I still do from time to time, that’s not entirely in my past, although for the most part it is. I don’t necessarily want to say one embarrassing thing about myself every column, or get into where it turns the whole enterprise into a bit of a self-deprecating joke.

So if anything, I’m a little bit wary of leaning too far into that premise. Because yes, I think it does function to give some credibility to the whole thing that I’m not going to judge you, I’m not somebody who is here to tell you how to never make a mistake. But I also don’t want it to turn into a self-deprecating stand-up bit about what a mess I am, because I don’t think that that is necessarily appealing either. And I think that women are particularly prone to that, making spectacles of themselves.

Twitter also creates a close-knit community. From an outside angle it seems like you’re a part of a generation of New York writers and people who are very online, and you’re at the center of that. How does that resonate with you?

I don’t know that I’ve ever had, or that any of us ever have, perfectly clear visions of ourselves. And so often when people will describe me, I find it very alienating because I think, “No, that’s not me at all.” And who knows, maybe it is, I don’t always have the best understanding of myself in the present. I’m usually pretty good at figuring out who I used to be. Who I am now is often a mystery to me. So I don’t know. I tend not to think of myself as a writer primarily. It’s something that I do from time to time—well, I hate writing. I hate, hate, hate writing. The only thing I enjoy about the writing process is being done with it.

I am not one of those weird freaks who thinks of writing as free therapy. It’s excruciating, I avoid it until panic and pressure from my editor take over and I have no choice but to sit down and bang something out. So I tend not to embrace the writer-as-lifestyle thing that some people do. And some people do in a kind of pathological way. There’s nothing particularly glamorous about working in media. I think that some people have a disordered relationship with that.

What motivates you to write and edit now besides paying the bills? Why write instead of doing something else?

I wish that I had a plethora of marketable skills, but I just don’t. I mean, I said I don’t enjoy the process of writing, and that’s definitely true. But there are aspects of it I like. It’s nice to be able to have a mandate to work through a problem, to think about something on behalf of another—in the case of the advice column—and I’ve often had little realizations about myself or the choices that I’ve made in the process of trying to figure out what somebody else might be asking me. That’s been rewarding. It’s also a very nice feeling when you put up a piece and a bunch of people say, “This is great, I loved it.” I am not immune to flattery, and so that part of it I like. That’s why I like having written something: When you get to put it up and have a bunch of people say, “I love this.”

There have certainly been points in my life when I became really incurious about the world, and those were always bad periods for me. Writing motivates me to be curious and to be interested in people and what they do, and why they do it. Cultivating a curiosity about the world is something that’s been important to me, not just on a professional level, but definitely on a personal one as well.

And it makes for better writing as well. There’s nothing worse than when you read something and you can tell that the writer just had no really good questions about the subject matter at hand or why they were thinking the way they were thinking. So there’s also a drive to get better at it. I am definitely somebody who lacks hustle, but I’m competitive with myself and so I like to keep writing because there are moments when I can see some definite improvements where I’m like, “Oh, I think that I said that in a way that I would not have been capable of a year ago.” That’s a really nice, rewarding feeling.

What’s your process like as far as from deciding what question you’re going to answer to the final draft?

Avoid and then panic. [laughs] So, I have a dedicated inbox for the fuck-up questions and I’ll try to keep an eye on it to see if anything jumps out at me, if there’s a question that seems like I haven’t answered anything like it before. A lot of questions unfortunately automatically disqualify themselves either because they’re not asking a question, that’s a big problem. Or they tend to be very information-light and so I just don’t have enough to work with. I would say probably 70 to 80 percent of them are just not something that I could use. So what’s left, I try to keep an eye on it to see if there’s anything that sparks my interest.

Although sometimes it’ll literally just be the day before my column is supposed to go up and I will take a look at the inbox and see what’s there. Then I usually will read them, and then go away and do something else for an hour, or a day, and then see if there’s one question that still bubbles to the surface that I’m still mulling over. And that’s usually how I end up picking them. And then I tend to write it the day that it goes up, because again panic is a good motivator for me. I need that outside pressure of somebody saying, “Are you going to file that? Where is it?”

I have no idea what the best way is. I only know the way that I have come to do it. That was also the way that I always wrote my papers in college and grad school. Largely to their detriment I used to really buy into that, like, “Oh, I work well under pressure.” And [now] I’m like, “No I don’t, I don’t.”

How do you know when something’s finished?

When I hit a minimum word count. [laughs]

I mean, that’s something that I would like to improve. I tend to rush through it, and want to hit a couple of points and then wrap things up and be done. I am trying to get better at giving something a little bit more space if it’s warranted. Again, because I don’t really enjoy the writing process and I put it off for so long I will sometimes think, after a piece is published, later that day, “Oh, I should have said this as well,” or “I gave this aspect of it short shrift and that wasn’t fair.” So I’m trying to get better at literally giving myself more time to start a little bit earlier.

I do need to let something marinate in my brain a little bit. And occasionally if I pick a question well in advance—like if I find one that I like a few days ahead of time—I will often end up writing most of the response in my notes app on my phone. I’ll just think of phrases, or sentences. I do, and this is a terrible confession to make, but I do sort of think in tweets, which means a lot of times my writing is a matter of getting from point to point to point to point to point that I’ve laid out in my Notes app.

An outline?

Yeah, an outline or at least phrases that I know will have an impact, or will be a nice break after a couple of long sentences—like one really good punchy one, or a good joke, or something that I feel is just a really interesting metaphor. Something that gives you a little bit of a break. I find when I’m reading, you will reach certain points that feel like you’ve been swimming for a while and you get to a little island you’re like, “Ahh.” I’m trying to find those moments. The columns that I know have a few of those invariably are the more successful ones.

And I keep my phone in my bathroom because the kicker always comes to you in the shower. That’s a lesson that I learned from my friend Amanda Mull. If you’re missing a kicker, hop in the shower, it’ll come. Often [it comes while] on the train or walking my dogs or something. The worst is when it happens just as I’m about to fall asleep and I think, “I’ll remember that.” I never do. I have lost my best sentences. I’m sure they were brilliant.

What do you need to have in place to write or work? As in, what physical elements, what kind of mindset?

I can work almost anywhere, I’m not particular about my physical location. I just need coffee. I used to think that I was a night person, but that was just because I liked drinking and staying up too late. I actually do tend to do better thinking in the late morning, so I will try to structure my day where that’s the time that I dedicate to doing structural edits on features, or doing my own writing, or something other than sending emails.

I don’t tend to listen to music when I write, which I think is weird, as a lot of people like to. I don’t, I find it distracting. I have two dogs, so hopefully [I] get both of them settled and not barking at me.

I do prefer to write at home. I will edit in coffee shops, and I’ll do other work in cafes. Maybe because I tend to be writing personal stuff, I feel a little bit exposed sitting in a coffee shop writing about the time I fucked an actual clown or something. Who knows who’s sitting beside you.

So editing and writing gives you a lot of independence and space. But with an advice column, you’re beholden to multiple people outside of yourself to produce something.

Yeah, that helps a lot. Often my boss would like me to write more often, and she has to really drag it out of me. It’s like pulling teeth because if it’s just something that I say, “Hey, I had an idea, somebody should write about this.” Then she’s like, “Well, you could.” And I’m like, “Well,” and then I sit with it for like a month. And then never get around to it.

But with the advice column, I definitely do feel a responsibility because people are putting trust in me by reaching out and wanting help. I am much better at meeting responsibilities to others than responsibilities to myself. Which actually is a primary theme of the column.

In the column you touch on how edging out of your fuck-up phase meant realizing this responsibility you have to others. It’s interesting that part of the act of making the column involves this responsibility to give someone good advice.

That has been a large part of me reorienting how I think about what it is to be a person. It really is about being in the world with others, and what we owe to each other. That can manifest in very small ways—like, I have agreed to do this column and people are writing in expecting me to maybe answer their questions and so I should meet that demand, through to having dogs who get me out of the house because they need to go outside even when I don’t feel like it. All the way through to a bunch of my very meaningful personal relationships… no longer seeing the demands of others as an imposition, but seeing it as just a way to be fully human.

Was becoming an editor and writer part of that reorientation, or coincidental?

It’s ongoing, so it’s not something where I think like, “Oh, June 12th, 2017, that’s the day I wrapped it all up and figured out how to be an adult.” It’s definitely an ongoing process. Now that you’ve brought up this theme, what I like about editing is that writers expect something from me, and so I like to work with them and try to make their writing better. I get very busy sometimes, but I am definitely much more unwilling to shirk my responsibility to writers—like, I’ve told this writer that I would have edits back to them by this date, so I’m going to do that. Whereas if I have an idea for a piece that I want to write, that idea could hold for six months and then I’ll never write it.

That can be a lacking quality in people in this city. Everyone has so many creative endeavors, and practical things like commuting are so difficult that people just flake out.

There has been a cultural turn towards this idea that life is hard so you should indulge your bad instincts whenever possible because the world wants so much from you, that it doesn’t matter if you flake on plans. My approach to financial responsibility is still very much like, “Lol, that surely won’t matter.” But I don’t know, I try to be in the world more as it gets harder and meaner.

Where do you draw inspiration from?

I read very, very widely and near constantly. I think you can tell when you are reading somebody who doesn’t themselves read very many other people. So far as I have any advice about writing, that would basically be it.

I am just consistently in awe of good writing. There are certain writers who provoke an almost electric thrill when you encounter their work, and when that goes away, again when I find myself uninterested in other people’s reading or other people’s thinking, that’s the biggest red flag that something has gone really off the rails and I need to do some work to get back.

One big change that I made a little while ago in my reading habits is that even though I am still very much an atheist and will almost certainly die one, I’ve been reading a lot more religious writers. Particularly because I am interested in how we can better have intellectual generosity, how we can tackle questions of what is good, and what is just.

There are a lot of writers of faith and people who write about faith who are adept at that. And so that’s been important to how I think about the world. [In] grad school certainly I read a lot of literary theory and there are ways in which that makes you cynical and suspicious and constantly on the lookout for where you can find fault. It was an active decision on my part to try to find people who are smart and thoughtful, but also compassionate in how they think.

As an advice columnist, do you have any other advice for writers and editors?

I don’t feel like I’m in a position to give advice to writers and editors. I guess I am in a unique position in that I came to media and writing for the internet a little bit later in life. So obviously there’s a bias about, well—how I did it clearly has some benefits, and I think it largely does. In so far that this is materially possible for people, it’s good to see the world and do things before you decide that you want to write about them sometimes.

Particularly for young women, there is often this pressure to immediately start thinking of all of your personal experiences in terms of content. That is incredibly destructive both to how you develop a personality, and also how you encounter your writing. I would say it’s a hard industry to be successful in and, who knows, The Outline could go out of business in six months and I might still write on occasion, but I would also be perfectly happy to just go get a marketing job somewhere. Well, I don’t know about perfectly happy, but I would do it.

When you say you came to writing later in life and the industry tends to ask for personal things from women—

There’s been a lot written about the personal essay economy and how that’s fallen by the wayside. A lot of that is good, it’s good that women are no longer getting paid like $75 by XO Jane to write about their sexual assault. That didn’t benefit anyone.

Because we haven’t really replaced that with any other kind of infrastructure for how women in particular might break into digital media or become writers, there’s still a sense that you need to write about things that have happened to you, or in your life, or things you have done. And I don’t think that that’s always the best way to think about your own life and your own self. I also don’t think that very young writers are necessarily the most equipped to write about or write in that genre always.

So coming at it a little bit older has given you more perspective.

I am much better at understanding myself five years ago than I am myself yesterday. And there’s a lot about digital media that will ask you to explain yourself from yesterday and not necessarily give people the time to figure out how they really feel about things. That’s not only just with personal essays, but the take economy and how you need to have an opinion about something, basically simultaneous with it happening. I don’t think that that necessarily leads any of us to our best thinking.

Twitter is fun and Twitter gave me my career, so I realize this sounds hypocritical to say, but I think that if it’s possible, try to get ideas elsewhere. And sometimes an editor’s going to assign you something, or you’re going to need to make 400 bucks writing a quick take about whatever happened yesterday, and that’s fine. But hold tight to the ideas that you care about that come from somewhere else and really spend your energy on those.