A week of journalism: How to be a freelancer without starving

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Here’s how I became a writer. I started writing when I was six and wrote nonstop, about things no one cared about.

Nineteen years later I thought, I like to write, I should get paid for this.

So I went to graduate school for writing, and the first day, the teacher said, “If any of you can imagine yourselves doing anything but writing, you should do that. Writing is hard, and lonely and full of rejection and you’ll never make any money.”

I stayed in school (I had a fellowship – who can give up free money?) but after school I got a job in marketing at a Fortune 500 company. And I made a lot of money.

But I kept writing. For ten more years. I wrote after work, and when my jobs were slow, I wrote at work. I used my vacation time to send writing to publishers who rejected me. But then they stopped rejecting me. And slowly, I realized that I could support my family with my writing. So I took the leap. (And, note, a huge salary cut.)

If you think you want to be a writer, first pay heed to my teacher’s advice. If you still want to write, remember that most writers spend years and years writing before they get published in a national magazine. So keep your day job until you’re sure you won’t starve. Here are three other things to do as well:

1. Rethink your ideas about time and space.
The best way to build up a freelancing career is to have another job with a steady paycheck, to support you while you’re honing your skills as a freelancer. This means that you need to be able to write in small, disjointed spurts of time, because you have a day job, and responsibilities, and you don’t have three days to craft each sentence.

But maybe you’ve already quit your day job as an expression of commitment to the freelancing. That’s fine, but maybe you don’t have a lot of money. Writers do not need their own pristine office and gorgeous PowerBook. I wrote for years on my kitchen counter because our New York City apartment didn’t have room for a desk. It wasn’t great, but it was fine.

2. Accept self-promotion as a way of life.
No one likes to do self-promotion, but the people who really, really want to work for themselves force themselves to be good at it. There is no one to get work for you except you. And it takes a lot of time to get the word out about what you do and why you do it well.

There are a ton of freelancers who can do a competent job at any given job. The freelancer who gets the work is the one who is best at marketing herself. So don’t talk about the injustice of the world and how you are too much of an artist to promote yourself. Instead, set aside 40% of your day for self-marketing. I used to think that as I got to be a better writer I would do less self-promoting. But in fact, it never happens, as far as I can tell. It’s forty percent forever.

3. Give up the notion that there’s one, perfect way to do it.
Not that the perfect word doesn’t exist. But it’s in the eye of the beholder. Who, in this case, is your editor. But look, you’re not writing the next Magna Charta. Maybe you’re writing a how-to piece for a men’s magazine. Or, if you’re lucky, you’re writing some travel piece about a hotel that’s giving you free lodging. What I’m saying here is that the stuff you’re writing isn’t so precious that the editor can’t rip it to shreds and rewrite it in his voice.

So what? You still get a check. You still get to say you were published in that magazine. Don’t write for that editor again if it’s so upsetting to you. But remember that the best money does not come from the best assignments, and there’s a reason for that.

So be flexible. I have found that when I took assignments that I didn’t like, I still learned a lot, even if the editor didn’t love my word choice. Focus on the learning, and the side benefit will be that you’ll have better relationships with editors. For a freelancer, the steady work comes from a combination of good work and good relationships.

Other posts from “A Week in Journalism” series:

Why do journalists misquote everyone (and how I met my husband)

How to move from print journalism to online journalism

Seven ways to get an agent’s attention (by my agent, Susan Rabiner)

37 replies
  1. Jenflex
    Jenflex says:

    Great commentary on writing as a profession, esp. that last item. All of it fits, even as a full-time staff writer in a private-sector, non-publishing job.

    Just curious: were the better-paying, less fun jobs also better learning experiences because of the editor’s skills? Seems like for the glamour writing jobs, the editor might be able to get away with being more of a jerk.

    * * * * * *
    The jobs I have learned the most from were the one’s I was the least prepared to do. I had very little reporting experience before I started writing for the Boston Globe. I think I learned the most possible from my first column I wrote for the Globe. The column went through fifteen rounds of editing and never ran. Basically, my editor was taking the time to show me how to write a newspaper column. I’m still grateful.


  2. Andrew Flusche
    Andrew Flusche says:

    Hi Penelope,

    This is a great post. Your points apply to many types of freelancing, beyond just writing. This is definitely one of your great qualities as a career columnist: transcending career boundaries.

    Take care,

    * * * * *

    Thank you, Andrew. I, too, think this advice applies to many types of freelancers. I think really, what unites all freelancers is the struggle to balance the need to market and the need spend time doing what they originally set out to do because they love doing it.

    Of course, you always bring the legal perspective to things. And you make me realize that even attorneys who strike out on their own have these issues.


  3. Rachel
    Rachel says:

    I’ve been reading this blog for a month or so and have been holding back. But “writers” is plural and does not need an apostrophe. In the reply to the comment, “ones” is plural and does not need an apostrophe. Just as a note, “it’s” means “it is”, and “its” is possesive, like “his” and “hers”.

    I’m a freelancer and had been waiting for a post like this. And even though, apparently, in the new work world, details don’t matter as much, I really am having trouble reading advice about writing from someone who doesn’t seem to proofread.

    I hate to leave a nasty comment, but some people DO notice these details.

    * * * * * *

    Hi, Rachel. I don’t think this is a nasty comment at all. I appreciate it. You are sort of a wake up call to me.

    There have been many discussions about typos on my blog. Which I will tell you about. But first, some background.

    I do not believe you need to be good at spelling to be a good writer. I don’t think you get hired for good attention to spelling. You get hired for voice, ideas, clever ways of saying things. Perfect grammar doesn’t get you hired as a writer, it gets you hired as a copyeditor. They are different skill sets. I get final edits back from high-level editors all the time that have spelling errors in them, and that’s becasue there is someone else to catch those errors.

    So, this was my reasonning when the woman who I hired to help me with stuff — editing and other stuff — said that I should let her go through the whole blog and corret my spelling errors. I told her it’s a blog, it doesn’t matter. It’s too fastidious for the medium. We went back and forth. She actually volunteered to do it for free. I said no to that, even.

    Then, my contact at LinkedIn mentioned somethign about how I should use Spellchecker. And then I thought, oh, that’s bad. LinkedIn is sponsoring me and they are commenting about errors. So yesterday (when that happened) I told the editor to go ahead and fix all the errors.

    I see, though, with the errors you point out, that I don’t actually know the rules. I am not good at the rules you are pointing out that I break. I need someone to check it. And, in fact, Spellchecker doesn’t pick up all the errors you point out.

    So, two things for us to take away from this discussion:

    For you: No one ever got to be a great writer because they were great at spelling and grammar. It takes something else.

    For me: My spelling and grammar errors have reached a tipping point of being totally annoying and someone needs to be fixing them if I can’t do it.

    Good learning for everyone here, I think. Thanks, Rachel.


  4. AjiNIMC
    AjiNIMC says:

     English is not my mother tongue and I always had problems in writing lucidly. I always read for information and became an artistic programmer, I am trying to catch up, any advice for people like us?

     * * * * *

    I  don’t really  know abou this. I’m sorry. But  maybe other people have some helpful tips?…


  5. Andrew Flusche
    Andrew Flusche says:


    Penelope’s so nice that she might remove this comment, but I’m going to leave it anyway…

    Why is it that every blog & forum has a few comment trolls? Instead of adding something positive with a critique, you just went after this great writer for a tiny grammatical typo in a 733 word article.

    Where’s the link to your work, so we can see what errors you make?

    Penelope, keep up your great writing!


  6. Frank Roche
    Frank Roche says:

    Excellent advice…and I think this applies to not only freelancers….young writers and designers need to know that they will get edited…it always seems a shock to them for the first year…being an artiste and $3.25 won’t buy them a cup of coffee at Starbucks!

  7. Recruiting Animal
    Recruiting Animal says:

    Penelope, great posting.

    Rachel, you spelled “possesive” wrong, I mean incorrectly.

    Andrew, you’re not a troll if you disagree. Being afraid to say something important to you is worse than saying something wrong. (But I still love you, The Recruiting Animal).

  8. Sujatha
    Sujatha says:

    Even though I’m not aspiring to be a writer, I still found this honest and practical advice very refreshing. Thanks!

  9. Brad Maier
    Brad Maier says:


    Would it be possible for you to comment further on what you do to market yourself during this “40%” time? Also, do you have any insight on locating the correct places to submit your work and how to find publications that might be interested in a piece?

    **To Rachel:

    I wonder how editors deal with your style. Though not grammatically incorrect, starting sentences with coordinating conjunctions is a bit odd. I’ve also never seen someone use commas and non-essential phrases so frequently. Perhaps you should think about reworking your sentence structure. Anyway, I found it much easier to read through Penelope’s typos than your comment, at least she added content I can use.

    * * * * * *

    That 40% of the time is tough to understand at first. The more you work as a writer, the more clear your goals for youreslf become. And when your goals are clear then you know how you should be marketing yourself. For example, Laura, below, commented about her book proposals. That’s marketing. Pitching stories is markeitng. So is networking with people who can give you work – even commenting on blogs :)

    Really, this question deserves a separate post — how to promote yourself. I’ll work on that. Stay tuned….


  10. Laura Vanderkam
    Laura Vanderkam says:

    Hi Penelope: I don’t know if I spend 40% of my time self-marketing (I probably should) but what’s crazy to me about freelance writing is the amount of time I spend on things that have no guarantee of ever paying off. Ever. I think I spent 80% of my mental energy today on projects that are not only not on the revenue line (is that Julie Morgenstern’s phrase?), it’s not even clear how close they are to it. This includes a non-fiction book proposal and a novel that’s a follow-up to a first novel that hasn’t even been sold yet. However, they are on the list of things I’d like to accomplish in life (ie, being a novelist, and making more of my non-fiction money from books). So I force myself to make time for them first. Laura

    * * * * * *

    This is a great comment. For those of you who are not noticing the commenter, Laura is someone who has made it big-time as a freelance writer. Take a look at what she’s doing. For one thing, she’s working on a novel that comes after the novel that has not been sold. She shows us how much faith you have to have in yourself  to just keep pushing and pushing and believing that something will work. Also, she shows us how much self-discipline you need to succeed as a freelancer. Her list is so self-generated. All deadlines appear to be self-imposed. For a freelancer, the drive has to come from within.

    in terms of marketing, I would say that anything you’re working on that is not guaranteed to pay off is actually marketing. You are doing something with the hope of catching someone’s eye and getting them to pay you. It’s much harder and much more other-focused than when you have a fee already sitting in your bank account, and you’re writing.


  11. Lea
    Lea says:

    As a former journalist, I have to tell you that copy editors — and pretty much all other editors, too — absolutely HATE to work with writers that have your attitude about spell-check, grammar, and following style. A lack of attention to details like that makes an editor think that you lack attention to details in every aspect of your story, which is directly linked to your credibility as a writer.

    Personally, I think it’s a sign of laziness to not care about details like spelling and grammar. If you don’t care enough about your writing to finesse the nuances, then why should I read you? Having voice and an ability to choose compelling topics and research them are all important as well. But what makes the good writers great is attention to detail in all aspects of their work.

    * * * * *  * *

    Lea, I think it’s safe to say that I am doing well as a journalist, which is testament to the fact that being bad with spelling and grammar does not necessarily hold one back in journalism.–Penelope

  12. Rachel
    Rachel says:

    Hello all,
    I just wanted to say that my goal was not to harp on small typos. I commented on the apostrophes because Penelope systematically misuses them, and it was obvious that, as she admits, she does not know the rules and is not paying anyone to check her work.

    This does not make her a bad person, or even a bad writer. It simply seems unprofessional to me, in a way that is not consistent with her work overall. I wanted Penelope to know that there are readers who care about these things.

  13. Sarah
    Sarah says:

    Hi Penelope

    Another excellent post! Every one of these points apply to freelance translators too, something that would have save me a lot of heartache had I realised when I first struck out a few years back.

    Funnily enough, the point about needing top notch spelling, grammar, etc. also applies to translators, as we are effectively writers between two cultures. But instead of putting me off, your occasional typos (the odd time I’m even conscious of them) only serve to further inspire me. If your blog was too perfect I'd probably be too freaked out to ever even try posting a comment myself :)


  14. Sandra Mendoza-Daly
    Sandra Mendoza-Daly says:

    I guess I am really confused about the job descriptions of editors and copy editors. If a writer needs to have perfect spelling and grammar, be able to craft a story, style sentences and write with a unique voice, what the heck do editors and copy editors do?

    Personally, I followed Penelope’s post without a hitch. Never even noticed the errors. And if you had an editor for your blog, I’m sure they would’ve caught the errors and moved on.

    Thank you for the valuable advice for freelancers Penelope. You once encouraged me,via email, to think about writing as a future career because medical conditions were forcing me to think about my future. I’m still thinking, but writing at the same time!


  15. Maureen Rogers
    Maureen Rogers says:

    People who want to forge a freelance career may also want to consider doing non-byline work for corporations.It may not be the great American novel, poem, or essay but it can be interesting and help pay the bills while you work on more creative things and/or pursue byline opportunities. I know a lot of “struggling writers”(poets, essayists, novelists, et al.) who take low paying, physically demanding jobs to support their art – but end up being too exhaustive to get much writing done at the end of the day. Corporate gigs pay better than waiting tables and bagging groceries,are closer to what you want to do in life (i.e., write), and leave you more time and energy for “the real deal.” And, no, it doesn’t have to mean selling out. (It does mean being practical.)

  16. Accidental Alpha
    Accidental Alpha says:

    I have to concur with your first point. When I first started, it was tempting to splurge on a home office. As it turns out, I work better in an easy chair with a TV tray on the side. My time has been far better spent writing than purchasing and decorating a home office. Going without the glamour is a good way to test whether freelancing is the right path for you.

  17. Neale Bayly
    Neale Bayly says:

    Love this topic. Having left school at 15 years of age with some scrappy education here and there since my grammer is not too hot. That hasn’t stopped me from making my living as a freelance writer for nearly a decade now. I have always thought copy editors did what they did because they aren’t writers, and it is nice to see a successful journalist with the same thought process. I employ a copy editor to check my stuff so I can spend more time being creative with my words. Hopefully I will learn something too. I am lucky, I get to write about my passion so it makes it easy. Enjoyed the comments here.

  18. Tim Kern
    Tim Kern says:

    There’s a lot of good in this post and in the comments. One more point worthy of inclusion is that, once you accept an assignment, you should not be late, even if you have a “good excuse.”

    Editors hate filling blank pages at the last minute, and they’ll do one of two things to the slow writer: either they’ll look for a replacement, or they’ll give you silly lead times and phony deadlines. Neither of these is as good a result as if you delivered on time. Editors know that things come up, and they’ll work with you, but not all the time; and when the opportunity to get a sub comes along, that’s what they’ll do. I get a lot of short-lead-time assignments that way, so on a personal level, I should be grateful.

    Nobody (even an editor) likes hassles; nobody likes to be dismissed. Late submissions get you put on a short, bad list.

    I’m a freelancer. I have written for sixteen magazines in the past year, many more than once and some as a columnist. Only when an assignment has changed mid-stream have I asked for an extension, and that happened once in over 200 published articles in the past four years or so.

    As for editing, I’ve edited literally tens of thousands of pieces (10-20 per day, 6 days a week, for over three years), and I feel that I’m typical when I agree with Lea that I consider sloppy writing (spelling, grammar, and punctuation) to be a trait symptomatic of laziness. Unlike Lea, I don’t care that my writers are lazy; I care that they’re supplying the message the readers want. (Most readers, too, can’t spell or punctuate.) Where I have trouble with these sloppy writers is that this kind of writing takes MY time as an editor, and I’m as lazy as the next guy.

    So, if you want to be successful, deliver good quality, on time. That’s infinitely better than delivering Ring Lardner a day after the press run closed.

  19. Tim Kern
    Tim Kern says:

    Oops — that’s “literally thousands.” It’s over ten thousand, but probably not “tens of thousands.” I’m a better writer than mathematician.

  20. Anne Hart
    Anne Hart says:

    What a wonderful article. I’ve been freelance since June 17, 1959 and have enjoyed doing this fulltime. I’ve written 81 books and am proud to have had a career now that I’m retired…as a full-time freelance writer of novels and nonfiction books as well as magazine articles. I still write freelance for magazines when I want to. It is a wonderful life….as a freelancer….and I thank all the intelligence in each parallel universe and beyond that I always had a husband with a job who paid the bills. Amen.

  21. Tim Kern
    Tim Kern says:

    Hi, Anne. When you say, “…I always had a husband with a job who paid the bills,” you’re not really giving advice about how to have freelancing pay the bills.
    On the other hand, I’ll concede you are answering the question: “How to be a freelancer without starving.” I guess that, if someone else’s work can finance your life, you can be anything you want to be.
    It’s tough, though, for us (those who make livings as freelancers) to compete against such subsidized talent. No offense; if I could do it that way, I would, too. Best of everything to you!

  22. Barbara Saunders
    Barbara Saunders says:

    Having worked as both a writer and an editor who is also a dyslexic, I have some empathy for Penelope’s proofreading deficiencies!

    The inner editor says: It’s easier to copyedit the work of someone who has interesting ideas than to make something interesting out of unoriginal thought that happens to be rendered in polished text.

    The inner writer says: It is very, very difficult to proofread one’s own work.

  23. mary speranza
    mary speranza says:

    speaking of entrepneur—-i am trying to get mss to read at home; for pay, not for free. no one has answered me. is it that you think my request laughable and you’re still laughing? i know that that service is out there; i just don’t know how to connect with it.
    i am a senior citizen and love to read. i’m basically shut in—-but don’t want to spend my time “doing nothing” i also am a published author myself.
    so someone get back to me, okay? it shouldn’t take long out of your day. just an email to write to, or a person to call on the phone! i would post here and thank you publically.
    please take this request seriously.
    mary speranza

  24. Brian J. D'Souza
    Brian J. D'Souza says:

    “What I'm saying here is that the stuff you're writing isn't so precious that the editor can't rip it to shreds and rewrite it in his voice.”

    For most people, especially inexperienced or untalented writers, this might be the case. If you’re an expert in your subject area, have a strong writers voice, are dealing with a sensitive subject matter and/or know exactly what you’re doing, you have to stand your ground.

    Above and beyond that, it is your name going on the work. You have to live with it. Your blanket statement doesn’t apply to everyone.

    • Fiona Marsden
      Fiona Marsden says:

      ‘”What I'm saying here is that the stuff you're writing isn't so precious that the editor can't rip it to shreds and rewrite it in his voice.”

      For most people, especially inexperienced or untalented writers, this might be the case. If you’re an expert in your subject area, have a strong writers voice, are dealing with a sensitive subject matter and/or know exactly what you’re doing, you have to stand your ground.

      Above and beyond that, it is your name going on the work. You have to live with it. Your blanket statement doesn’t apply to everyone.’

      Yep Brian, I agree with you. It’s one thing for an editor to make minor changes to an article; you just have to accept that. But if they make huge, sweeping changes (particularly without consulting you first) then you have to speak up.

      What’s the point of having your byline on something that doesn’t fairly represent your work? The pride you feel on seeing my byline against an article will fade rapidly when you realise that what’s been printed isn’t what you wrote. Believe me, I know from experience!

  25. Makarska apartments
    Makarska apartments says:

    You said “I like to write, I should get paid for this.”

    I think its an essential thing whether your writer or whatever your trying to be.

    Do what you’re good at and put some effort in it and only sky is the limit :)

  26. Martin Prest
    Martin Prest says:


    I can only think of one thing I want to do as much as I want to write: act. Sadly, neither writing nor acting are renowned for great pay at the start (or the finish).

    I committed a terrible sin and abandoned a growing alcoholism blog last year. I should have looked for advice like this before!

    Martin Prest

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