A Freelance Internet Writer’s Hot Take on Freelance Internet Writing

P.E. Moskowitz
Aug 23, 2017 · 5 min read

At the recommendation of friend and all-around-good-person Harron Walker, I’m gonna share some info on what it’s like to make a living as an independent internet writer. And as Harron and others have offered, I am also willing to share contacts with writers (check out petermoskowitz.com for the places I’ve worked and email me if you need a contact there).

First, if you’re not already on it, sign up for the media listserv I run. It’s $1 a month for media workers of color. I know it’s a self-plug, but I really think it’s worth it (and you can cancel whenever if it’s not): Patreon.com/StudyHall.

Second, I think Jessica Glazer’s tips are fantastic. She’s right on the money about pitching. So read that before this.

Third, a huge caveat: freelance writing, at least for me, takes being in a relatively privileged position to begin with. Since I began freelancing in 2014, I’ve always made enough money to pay rent and nearly everything else, but without a financial safety net I’d likely be working full-time instead. I had a mental health crisis about a year ago, and because insurance is terrible in the United States, I had to rely on family to help me pay for treatment. If I didn’t have that I’d be looking for full-time work so I could have better coverage that pays for therapy. I think that really really sucks, but I think it’s important to mention just so I’m being totally honest about what freelancing is like.

Okay, onto the tips:

  1. Organization Will Save Your Life

As a freelancer I need to know what I’m working on today, tomorrow, next week, next month. I need to know how much money I’m owed, by which publications, how much I’ve been paid in a given year (publications often forget to send end-of-year tax forms), my expenses (so I can deduct them from my taxes — remember to expense everything you can). I also want to keep track of my ideas, my pitches, my contacts, and everything else.

So I currently have the following Google Docs:

  • The List: a list of things I need to do today, this week, and next month — basically it’s a calender but more flexible.
  • Pitches: a Google Sheet with columns for the title, description, possible pubs, relevant links/info for, and status of each pitch idea I have (am I working on it, is it just an idea, have I pitched it, did it get greenlit?).
  • Assignments: a Google Sheet with all assignments, who they’re for, when they’re due, what I’m being paid for them, and what status they’re in (waiting to start, in progress, edits, invoiced, paid, killed, etc.)
  • Income/expenses: Who paid me — how much and when on one side, what I spent for everything related to work on the other side. Save all your receipts!!!!!
  • Diary: Freelancing is stressful, so this is necessary.
  • Contacts: Every contact I have, on one sheet.

2. Work Smart, Not Hard (or Work Smart and Hard, but Not Stupid and Hard)

Give yourself days for discrete tasks. Compile pitches on one day, email editors on another (I think Tue-Thur is best), set days aside for writing, and set days aside for dealing with your finances. If you take it all as it comes, trying to do everything at once, you will get extremely flustered and burn out.

3. Start Slow, Ask for Help

Start freelancing a little bit at a time if possible. When you’re first starting to freelance, it’s tremendously helpful to have other income, whether it’s from a job, a part-time thing, sponsored content, whatever. As Larissa Pham has suggested, it’s easier to write if you have a job because it takes away the stress of making enough by doing good writing, and it puts you more into the real-world, where you’ll find story ideas .

Freelancing is really unequal in a lot of ways but it’s also more democratic than full time jobs in the sense that most editors will not know which college you went to, or if you went to college, when you pitch them. They also won’t necessarily know how many years of experience you’ve had. If you prove yourself a good writer, are good at pitching, and have a few clips that’s usually sufficient. Having three good stories that you’ve written over the course of a year or two is WAYYYYYYY better when it comes time to show an editor your work than having a consistent output of mediocre stuff. So try to go for those more ambitious, voicey pieces that prove your writing skills, as opposed to just trying to land stuff everywhere.

And don’t be afraid to ask for help, especially from fellow writers, and even from editors. Some writers and editors are assholes. That is indisputable. You will get nasty rejections, you will get snide remarks. But the more you ask for help, the more help you’ll get — contacts, pitch advice, really anything.

4. It’s all about relationships

90 percent of my money comes from editors I’ve worked with for years. If you like someone, keep writing for them. Give them some of your best stories, treat them with a lot of respect. I have a few publications I write for regularly, and then I try to develop relationships outside when I have story ideas I think will fit for other publications.

So build relationships.

I hate schmoozing as much as (actually probably more than) anyone. Don’t schmooze. Fuck schmoozing. I’ve never landed a story through small talk. But make friends with fellow writers who do the kind of work you like, talk shit with them about the media, have fun.

If you want any contacts, advice, etc, email me: peter.moskowitz@gmail.com.

Some screenshots of my organizational docs:

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P.E. Moskowitz

Written by

Writer, journalist, etc. Author of The Case Against Free Speech (https://amzn.to/31CFMk6) and How to Kill a City (https://amzn.to/31G2Ezi). they/them/theirs.

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