Ann Friedman is a freelance journalist who writes about gender, media, technology, and culture. She writes a weekly column at NYmag.com and contributes regularly to The Los Angeles Times, ELLE, and The Guardian. She also co-hosts the popular podcast Call Your Girlfriend. I first came across Ann's work through her newsletter and admired her wittiness, and intelligent writing. She's spent the last three years crafting her ideal role, and I was so excited to learn more about how she fell into being self-employed and how she continues to hustle to do the work she loves. I took a lot away from our conversation and know you will too.

Tell me a bit about what you’re working on right now?

If I have one overarching role it's as CEO of the corporation I've made to oversee all of the stuff that I do. There are two things that, financially and in terms of my time, are guiding my weeks right now. One is my column in New York Magazine which I've done for three and a half years now. It's a weekly column, although I do skip the occasional week. It’s about politics, gender and culture which is, as you may have noticed, three fairly broad topics, so I have a lot of leeway to figure out what I want to write about.

The other thing that is taking up a lot of my time, is the podcast that I do with two friends, called Call Your Girlfriend. We're just at the stage where we're starting to sell ads against it, we're launching a newsletter related to it, and starting to plan more live events. At this time last year it was something that I was doing but wasn't so much a part of my working day.

I'm also working on my own email newsletter, which I started a monetization scheme for towards the end of last year and I'm kind of fine tuning that. In addition, I'm working on some freelance profiles for some magazines in the UK right now.

Those are the four big things: my New York column, the podcast, my newsletter and these freelance profiles are the main stuff I’ve got going on right now.

What was your path to initially going out on your own and why do you choose to remain working that way?

I got fired which is how I became a freelancer [laughs]. Statistically, when you look at entrepreneurs most people come to working for themselves because they were booted from a cozy, full-time position. It was something that I had thought about for a long time, but I don't know if I would have taken the initiative to do it without the prompt of being actively ejected from my job as an editor.

At first, I thought it was just a phase while I job hunted, I said to myself “you know I'm going to do freelance writing while I apply to jobs.” I landed the New York Magazine column within in a couple of months. It became clear that maybe if I did that, and I got a couple other columns, that would be steady. So it started to feel a little more feasible after that. I think it actually took a full year, maybe more before I could confidently answer that I was a self-employed writer when people asked me at parties. Identifying myself as a self-employed writer was the first part of the battle.

I stay freelance because there's a lot of freedom in it. For example, two days ago a friend of mine I don't get to see often, she just came over and we hung out and painted watercolors in my house for two hours, from 2-4pm. Then she left and I did work.

Obviously, that's not a representative day. There's some days when I am chained to my desk and working the whole time. That type of thing where I can construct my own schedule, it's nice. Also, as a journalist it's really nice if an editor I work with says they're not interested in something, I can just find another editor or maybe I can talk about it on the podcast. The fact that I can both create my own outlets for things that I think are important and find other outlets if I need to is really, really liberating.

How do you know when it's time to try something new or find a different challenge? For example, doing something like the podcast or taking on another endeavor?

I thought of 2015 as the first year of my career that I didn't start something, like the newsletter in 2013, we started the podcast in 2014. Then I realized that 2015 was the year that I actually incorporated and in some ways I think of it as the year that I really started to think of myself as a business. All that is to say that I actually feel like I have the opposite problem, I want to start so many things all the time and at a certain point it's clear that I have a lot of demands on my plate. They're all things that I'm interested in and it's possible to juggle them but there's this core of what I do, which is writing.

That's true both in terms of how I make my money and how I self-identify. I didn't do the best writing I've ever done in my career in 2015. I did a lot of really cool stuff that I'm proud of but it wasn't the year where I can point to my writing and be like, "yes I killed it this year." That's something that I'm mindful of.

If I want to produce better writing even though it doesn't feel as exciting or sexy to me the way that figuring out a podcast business strategy does. I have to stop starting new things.

What would you say are the most challenging aspects of the work that you do right now?

I have a macro challenge of trying to make time to focus on getting better at the skills that I think of as core to who I am and what I do. I think that there is also a fundamental problem or difficulty in what I do which is what I take in, who I interview, or who I am writing about versus what I put out, like my own ideas that I put out or things that I make.

There's a tension between the skill sets of being a fact gatherer versus an opinion producer or a producer of stuff like the podcast, which is mostly my opinion and my friend's opinion. That tension is something that I think about and struggle with.

In a typical day or a week, how do you divide your time? Are there strategies you use to make sure that everything that's important is getting the attention it needs?

I think I'm constantly trying to get better at this. There's certain things that give structure to my week. In the beginning of the week, I decide with my editor on a column idea. At the end of the week, I send out my newsletter and we publish the podcast. There's more flexibility in between. I have certain things that I do on certain days of the week, like I put together the newsletter on Friday morning. Every week is different. Every day is different.

I try to adhere to a schedule where if I have something that's mentally taxing, or a writing assignment that I want to devote my best brain to, I do it first thing, in the 7am to 11am range. I try to schedule it, which is a little difficult for me sometimes because I'm on the West Coast. The East Coast is available for phone calls and stuff like that earlier in the day. I vastly prefer to do things like the conversation we're having now in the afternoon, which is the time where I do stuff that doesn't require so much concentration.

What was the most recent time you can think of that you either did something that scared you or took you out of your comfort zone?

This relates to what I was saying about being a reporter and gathering stories and information versus just my opinions. I have a really good friend who's a photographer. She and I, for a long time, have been trying to collaborate on something. In the fall, we went on a reporting trip together which was a full week where both of us were out of our element. We were talking to strangers and laying the groundwork for the project we want to do together. That was something that was a leap because it takes me out of producing work that pays me for a week, which is very difficult psychologically [laughs]. You're just saying, "I'm going to have a week where I'm not invoicing anything."

It was also an outlay of money. I bought my ticket to go and meet up with her. Also, just skills wise it's a stretch. It's not that I haven't done any reporting in the field. I definitely have, but a lot of the work that I do these days is interviewing people who want to be interviewed. They're people who have agreed to be profiled or they're experts who are excited to share what they know. It's less likely that I talk to someone who's reluctant to talk to me. Even though that's something I've done before, it's not something I do daily anymore. That was hard and it was good.

What are the five tools you use on a regular basis?

Simple Note - It's not the notes one in an iPhone, but I have tons of different pages that are ongoing ideas and notes from all these different projects to things I have going on. I have one that's where I keep just general ideas, things I want to write about, people I want to talk to, anything that might be a little thread I want to pull from for work. Anyway, that is a system that encourages me to continually come up with ideas and is a concrete thing that I look at and use, which is pretty crucial to what I do.

Calendar - I think the other thing is trying to actually put on the calendar when I want to take time for things. That doesn't mean I schedule out my whole day. I tried to do that and I failed miserably. It's sort of saying, "Okay, this editor is asking for pitches. I'm not going to do it unless I carve out an hour here to think about those." It's never going to have a deadline against it. It's not going to be a priority, so I have to try to create one.

Time of day - Trying to play to my strengths at different times of the day is important. Leaving the morning for writing time or other intense work is a productivity tool for sure. The better I am at sticking to that schedule, the better my work is.

Google Docs - I know a lot of writers who use Scrivener and maybe if I ever wrote a book and needed a footnote in it or something I would use that. I just use Google Docs, which most of my editors find easy for sharing and pretty simple to use.

Echo Smartpen - It's also a recording device that syncs with a special notebook. You take notes and have a full audio file and if you want to listen to the audio clip from the moment when you wrote a certain note, you just tap that note again and it will play back the audio from when you wrote it. That's very nice. It's also not intrusive to be holding a pen, psychologically. I mean, it helps to interview people that way without staring at your phone.

How do you manage your time between communications and email versus heads down writing or the other work that you need to do?

Yeah, I think it's a challenge. I think I would probably be more productive if I didn't sit with my email open all day. I am a sucker, like everyone is, for clicking on those articles about how to work better. They say, "don't leave your email open all day." I get it. There's also a lot of work that I do that is based in email. Reaching out to people to interview them or corresponding with editors and that is real work, that is not busy work. I associate bullshit busy work with being on staff somewhere. I'm never in a meeting where it's like, "Ugh, what am I doing in this time suck meeting?" It's not part of my life. Thank you, person who fired me.

It can be tough to concentrate when I'm writing. It honestly helps me to go into full-screen mode too, whether it's Google Docs or Word, where I just can't see any other options. That's sometimes very helpful to me.

Why do you do what you do? What makes it meaningful to you?

I think the answer is slightly different for all the different types of work that I do. I'm really interested in people and in strangers and in learning about new things. Being a journalist is like a hall pass into the things I want to learn more about. I can invent an excuse to call pretty much anyone, doesn't mean they'll talk to me, but that's built in and I really like that.

For the opinion type work, I would say that my motivation is giving a structure or a framework or a language for things. Things that maybe many of us have noticed before, or felt, but not been able to articulate why it's annoying or why it's great. I think that giving a language for things, or a vocabulary for them, is really important. I can think of the things that I've read where I've thought "oh, that's a name for that phenomenon." It's so powerful and revelatory, and then it gives that shared vocabulary to other people who are experiencing it.

I think that at it's best, the sort of opinion and essay work that I do, does that. That's a motivation for me personally as well. I want to figure out what these things have in common or why this thing is annoying me, or what to call it when dudes do that, or whatever. That's a motivation.

Who would you want to see featured on Ways We Work?

Kenesha Sneed, illustrator and ceramicist.
Gracy Obuchowicz, self-care coach.
Samhita Mukhopadhyay, dating-book author and editorial director at Identities Mic
Lara Shipley, photographer.
Jos Truitt, writer, artist and activist.
Rachel Kaadzi Ghansah, journalist.
Ali Liebegott, poet, artist, and writer for Transparent.
Myisha Battle, sex coach.
Of course my podcast partners in crime Aminatou Sow and Gina Delvac.