Writing Lessons

What I've learned in a decade of #FreelanceLife

Lesson One: Adopt a leggy assistant.

Hello lovelies,

I hope your new year is going swimmingly so far. Because it’s 2020, everyone has been doing the decade-in-review thing, and I finally did the math and realized I’ve been writing as a job for more than a decade (how??). I went full-time freelance in the spring of 2012, but spent years before that building up a part-time freelance career to make that transition possible. I remain very, very far from an expert, but I feel incredibly lucky that I’ve been able to make this career work. Some writers are able to get to stability because they have significant financial support from parents, a spouse, or some other resource, and that’s wonderful. I did not — although I did build up a little savings during my law firm days (I also left practicing law still holding six-figure student loan debt), and for the first time in almost ten years I have decent health insurance (thank you husband with a traditional journalism job). And to be honest I wouldn’t say that I feel financially or professionally stable, which is… not where I expected to be at 36. But I do feel professionally and personally happy. I feel good about the work I’ve done. I feel optimistic about where things are headed. I feel absurdly grateful to get to do this work, which I maintain is the greatest job in the world.

I still have a lot to learn. But I’ve also learned a little bit along the way. So if you are a writer, or an aspiring writer, or really anyone looking to write for publication, I’m hopeful that the below lessons learned over the past decade can be helpful.

  1. Done is better than perfect

    This is a Sheryl Sandberg-ism (my sincerest apologies) but in the freelance game, it’s true: Editors set up their schedules assuming you will meet your deadlines. Turning in your work when it’s due is crucial to remaining on the list of people they turn to. It sounds really simple, but apparently a lot of writers regularly blow deadlines, which makes you seem flaky and unreliable. It’s better to turn something in on time that isn’t a perfectly polished and gorgeous piece of prose than to turn a slightly better thing in a week late (especially if you’re getting an edit — you’ll have time to make it shine).

  2. File clean copy

    Nothing will make you seem like an amateur more than turning in a piece riddled with grammar and spelling errors. A typo is not a huge deal; multiple typos or sentence fragments create extra unnecessary work for your editor. And definitely triple-check any factual claims, statistics, numbers, etc in your piece — most online publications do not fact-check, and having to issue a correction is really embarrassing. It happens to the best of us, but it really shouldn’t happen very often (shoot for no more than once or twice in a decade). If you want to get more work as a writer, one of the most effective ways is to make yourself easy to work with — and that means filing clean.

  3. Be grateful for your editor

    It’s actually kind of amazing how many publications don’t edit — or how many won’t edit, or will give a very light edit, if your copy is clean and you don’t make mistakes. This is great because it means less work for you, the writer, but it’s also great when you come across that unicorn of an editor who does a deep dive into your piece. I love when I get a Word doc back full of track changes. Is it a blow to the ego to be reminded that my words are not solid gold? Of course. But take a step back and recognize that more eyes on the thing means a better end product. Good editing is a gift. Be grateful for it, not resentful or annoyed. And if you are resentful or annoyed, then (1) this may not be the right career path for you, and (2) do not, under any circumstances, complain either to your editor or publicly on social media. Complain to your friends, bitch to your partner, but keep it off of Twitter, Facebook and Instagram. I am absolutely stunned by the number of people I see — usually folks in academia who have full-time jobs elsewhere — publicly whining about getting a heavy edit, or having a piece killed by a publication. That’s the game, my friends. Play ball or get out.

  4. Don’t burn bridges

    Be mindful about how you write about your own industry, especially in public, especially on social media. That doesn’t mean you can’t critique specific pieces. It doesn’t mean you can’t highlight problematic trends or comment on bad editorial decisions. I write for the New York Times, and I often criticize op/eds from, say, Bret Stephens; I often question the wisdom of a particular headline, or the latent misogyny in a reported piece, or why zero women feature into any given story. What I don’t do is say “The New York Times is garbage because they published X thing I think is wrong, so I’m canceling my subscription.” First, that’s not true — the Times specifically is genuinely one of the best publications in the world, and I am honored to write for them — and second, tarring an entire publication based on one bad piece (or even a series of bad pieces by one person, or handful of screw-ups) is probably a mistake. There are of course exceptions. Some publications are universally terrible and deserve all the derision. But be thoughtful about who and how you criticize. Is it actually true that the entire publication is meritless? Is it actually true that all of the people who work there are bad and immoral? If we’re talking about, say, Gateway Pundit or The Federalist, then yes maybe! But apart from hard ideological pseudo-journalism, be more circumspect — both because it’s always complicated and because you never know who you’re going to work for in the future. It’s true that you can get a lot of retweets and follows by going on the offensive on social media, especially against the editors and publications that are seen as powerful and influential. But also, if editors see you making a name for yourself primarily by trashing other publications — instead of, say, contributing substantive work to the public conversation, or being specific and thoughtful in your criticisms — they’re also going to see you as a liability, no matter how many Twitter followers you have. Cast a critical eye on the media. But do so with specificity, integrity, nuance and honesty instead of seeking the ego-boost of yelling into the outrage machine.

  5. Be available

    This is another really basic one, but if you’re trying to make a writing career work — especially a freelance career — you need to be responsive and you need to be available. Answer your emails. Reply to editors. Even if you’re saying no, it’s better to write back ASAP than to make them wait. Full-time freelance work is profoundly inconvenient. I’ve responded to edits at dinner on my wedding anniversary, from my bed in between bouts of food-poisoned vomiting, and on New Years Eve this very year. I’ve filed from the back of a rickshaw in rural India, from a long-planned romantic vacation, from a 4x4 on bumpy carsickness-inducing roads when I was working on a totally different story, and from more taxis and subways and buses and trains and planes than I can count. That doesn’t mean you can’t carve out time for yourself — you can and if you don’t want to lose your mind, you must — but this is a hustle. If you want to work between the hours of 9am and 5pm and have weekends off, it’s not the right career for you (at least not until you’re really really famous and can do whatever you want — lemme know when you get there). But if you’re willing to be responsive and available at sometimes inconvenient times in exchange for a life where you generally get to work from anywhere in the world, where you decide your own pace and workload (and where you alone either reap the benefits or suffer the consequences) and where you have incredible flexibility, well — let’s just say I would not trade this for just about any desk job. (Unless some great publication wants to make me their roving international columnist, then call me).

  6. Get paid

    Please do not work for free. It’s tempting, especially when you’re just starting out, to accept the bullshit promise of “a great platform” as compensation for your work. Don’t do that. It’s terrible both for your own career and for this entire industry. Your labor is worth something more than “a platform,” and it devalues you and your work if you don’t get paid for it. It makes you look like an amateur. It decreases your editor’s view of your competence and your abilities. It also sets a standard of writers not getting paid, which drives down compensation for all of us. So even if writing is a hobby for you and you don’t need the money, get paid anyway. Money is literally the only way anyone in this industry shows that they value your work. Get it. Negotiate for more of it. Don’t feel bad about it. And definitely don’t criticize other people for getting it. Yeah, there are a tiny number of people who get paid $4 or $15 a word (I’m not one of them). Don’t trash or resent them; push for better pay across the board. Start by pushing for it for yourself.

  7. Celebrate the (deservedly) successful

    So many of us operate from a scarcity mentality in this industry, feeling jealous or bitter when we see someone else succeed — as if their success means fewer opportunities for us. I am as guilty of this as anyone. It’s one thing to feel frustrated when someone who is really bad at their job or is a legitimately terrible writer gets an opportunity or a platform you wanted; it’s even worse to feel resentful of people you like and admire who seem to be moving up faster than you, or going in a direction you covet. It’s also totally normal to feel that way, so don’t spend a whole lot of time beating yourself up. But do remind yourself that excellence begets excellence, and the more people who do well writing about the things you also write about means the more space for that stuff. This has definitely been true of writing about gender, race and social justice: The more that was put into the universe, the more demand was created, and more opportunities opened up. There’s no longer one single Feminist Columnist who has the single coveted gig. And that’s true across the media industry. So when you see folks who are doing well, even if you feel a little twinge of jealous, let them know that you admire them. Send your congratulations. Share their good work. Try to remind yourself that they are paving the way for more good stuff to come — including for you.

  8. Be generous, be kind, be respectful of people’s time — and give the same to yourself

    When you’re first starting out as a writer — or in any industry — you should absolutely reach out to the people whose careers you admire if you need advice. But be thoughtful about what it is that you actually want, and how you are spending that person’s time. Come in with concrete questions they might actually be able to answer (and that you actually want the answers to — not just questions you’re asking because you feel like you should have something to ask). Be thoughtful about the medium you connect in. Can this be done over email? (If what you really want to ask is, “Can you connect me with your editor?” then yes, that can be done over email). Can this be done in a phone call? There may be a very good reason to connect in person over coffee or lunch, but know what that is, and let the person you’re requesting time from pick a convenient date, time and place. Know what you’re seeking and how the person you’re talking to could be helpful to you. Be direct — they’re there because they want to help, but they can’t divine what you need, so tell them. Say thank you.

    At some point, you’ll be the person who is being asked for advice. Give it. Be generous with your time and your ideas and your feedback. Consider how many people gave you a hand, and see if you can behave in kind. Be especially generous to folks who may not have other hands up — the folks who don’t have connections, aren’t the kid of anyone important, didn’t go to the fancy schools, are just scrapping and trying. There are so many promising writers who don’t come from privileged backgrounds who are pushed out of this industry. Be someone who pulls them in.

    At some point, you may be a person who gets asked for advice a lot. You may have many, many requests every month or every week or every day. You may have acquaintances who ask you to please talk to this or that friend or mentee or relative of theirs. You may have the experience, over and over again, of offering your time only to have it pretty thoroughly wasted by a person who wants to “pick your brain” but doesn’t actually have anything to say or to ask you, who just wants to “connect” or “network” without any substance, or who perhaps has been assigned by a professor or teacher to talk to you but who could not care less. You may find yourself very frustrated by this. It’s ok to decide you want to invest your time wisely when it comes to advice-giving and mentorship. You can ask over email: “How can I specifically be helpful to you?” You can set clear time parameters for a conversation. You can say no if there’s a clear reason to say no (you’re generally overwhelmed and out of time is a clear reason).

    But this industry is inherently connective. You will succeed thanks to the help and work of others. Your best work will be thanks to years of groundwork being set, the bricks laid by people who are not you. You did not build the road you walk on. Cultivate that gratitude. Look backward at who you might help along. Smooth the path for those walking behind you.

  9. Lean into your strengths

    Different writers offer different things. It can take a while to figure out what yours are, but be thoughtful about what you do well and what sets you apart from the pack — and recognize that sometimes, what you see as a weakness is actually really useful. For example: When I started blogging, my co-blogger Lauren was incredible about writing about her own life. Her posts were deep and lyrical; they fostered intimacy and community. I was… not so good at that. Writing about myself felt uncomfortable and stilted; I wrote from a place of fear of being picked apart, not from any space of authenticity or serious self-examination. I tried and I tried, but it never clicked, and at the time, that felt like a failure. Now, many years later, I’m glad I didn’t keep pushing myself down a path that never felt like it was mine. I’m glad I leaned into writing about ideas that interested me and issues I felt strongly about. I’m glad I built up some expertise for myself in certain areas that had nothing to do with my own life. I still love reading great personal essays, and I still envy that particular set of writing skills. But I’m also glad that I took a good hard look at what I was actually good at and decided to build a career primarily from that toolbox.

    Another example: When it comes to op/eds, I write really, really fast. I think this is also left over from my blogging days, when I got used to posting multiple times a day without being too precious about my words. It didn’t have to be perfect; it just had to be interesting and good enough and live on the site. As a full-time freelancer now, that is how I make enough money to pay New York City rent: I write and publish all the time. I get an assignment at 10am and I file it before noon. When I realized that was a skill both rare and in high demand, I sought out a few places where I could consistently write and publish day-off, and set aside a few days of my week for these quick-hit pieces. It’s made my income and my workflow more consistent.

    That doesn’t have to be you. Maybe you write at a turtle’s pace, but what you’re really great at is telling a long and complex story. How can you maximize that strength? (Not by pitching quick-hit hot takes, for one). Maybe you’re great at distilling down a set of seemingly unrelated events into one coherent narrative about the state of things. Work with that. You don’t have to be good at one single thing, but it is worth giving some thought to where you’re strongest — especially if you’re just starting out.

  10. Take risks to grow

    You don’t have to have a five-year plan or a dream job or even a clear vision of where you want your career to go (I sure don’t, and never have). But it is useful to have an idea — many ideas! — about the kind of work you want to put out in the world. And it’s especially useful to see those ideas change over time. For most of my career, I’ve loved writing opinion pieces and being a columnist. But I’ve also been doing that for a decade-plus now, and I’m finding myself more drawn to reporting, magazine writing, and story-telling. None of that comes as easily to me — not the skills themselves, nor the opportunities. But when I think about the work I’m proudest of, it’s my magazine pieces. When I think about what feels challenging in the best of ways — when I think about which pieces keep me up at night, which ones make me obsessive, which ones I often avoid because they are so all-consuming and I am so terrified of fucking them up — it’s the long-form narrative nonfiction ones, the ones I spend months reporting out and conceptualizing. What keeps you up at night? What are you dreaming about but not doing? What do you read and think, that was beautiful — and I want to do that? If you’ve developed your own strengths and you feel steady in your work, where can you take a leap — or at least a big step — toward something fresh and scary?

  11. Just write

    That’s it. That’s the biggest piece of advice I have. Put words on the page. They are not your children; don’t get attached to them, and never fall in love with them. You want to write? Write. It doesn’t have to be good. The “delete” key exists. Give yourself permission to write crap. Some days you are going to write a steaming pile. And other days, you’re gonna polish that turd into gold. But you have to put the words down, and put them down again, and put them down again. Take some time. Then go back and read them. Ask yourself which ones you need. Ask yourself: Does this word say precisely what I really mean? Does this sentence say precisely what I really mean? Do I need every paragraph of this piece? Do I need every sentence of this paragraph? Do I need every word of this sentence? Cut the fat. Fill in the gaps. Cut it again. I promise: You will get to good. And then you will get to great.

Happy writing, loves.

xx Jill